n-(4(n-((2-amino-4-hydroxy-6-quinazolinyl)methyl)prop-2-ynylamino)benzoyl)-l-glutamic acid profile

ID Source	ID
PubMed CID	135402053
CHEMBL ID	422395
MeSH ID	M0099304

Synonym
NCI60_002838
ici-155387
nsc-327182
nsc327182
l-glutamic acid,4-dihydro-4-oxo-6-quinazolinyl)methyl]-2-propynylamino]benzoyl]-
n(10)-propargyl-5,8-dideazafolate
ici 155387
n-(4(n-((2-amino-4-hydroxy-6-quinazolinyl)methyl)prop-2-ynylamino)benzoyl)-l-glutamic acid
l-glutamic acid, n-(4-(((2-amino-1,4-dihydro-4-oxo-6-quinazolinyl)methyl)-2-propynylamino)benzoyl)-
nsc 327182
5,8-dideaza-n(10)propargylfolic acid
n(sup 10)-propargyl-5,8-dideazafolic acid
n-(4-(((n-(2-amino-4-hydroxy-6-quinazolinyl)methyl)prop-2-ynilamino)benzoyl))-l-glutamic acid
n-(4-(n-((2-amino-3,4-dihydro-4-oxo-6-quinazolinyl)methyl)-n-prop-2-ynylamino)benzoyl)glutamic acid
CHEMBL422395 ,
2-{4-[(2-amino-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid(n10-propargyl-5,8-dideazafolate, pddf)
2-{4-[(2-amino-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid (pddf)
bdbm50008294
2-{4-[(2-amino-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid(pddf)
2-(4-(((2-amino-4-oxo-1,4-dihydroquinazolin-6-yl)methyl)(prop-2-ynyl)amino)benzamido)pentanedioic acid
2-{4-[(2-amino-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid
PD084553

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Thymidylate synthase	Escherichia coli	IC50 (µMol)	0.0552	0.0190	2.5896	10.0000	AID211082; AID211444; AID282789; AID391733
Thymidylate synthase	Escherichia coli	Ki	0.0030	0.0030	0.0687	0.1500	AID211633
Dihydrofolate reductase	Homo sapiens (human)	IC50 (µMol)	5.0171	0.0006	0.8726	7.3000	AID282785; AID391734; AID56149; AID56150; AID56811; AID56813; AID57111
Dihydrofolate reductase	Mus musculus (house mouse)	IC50 (µMol)	6.8000	0.0020	0.9969	7.0000	AID57301; AID57306
Dihydrofolate reductase	Mus musculus (house mouse)	Ki	0.0140	0.0000	0.2171	3.9000	AID57445
Dihydrofolate reductase	Lacticaseibacillus casei	IC50 (µMol)	3.2740	0.0013	0.2696	4.9000	AID57749; AID57751; AID57755
Thymidylate synthase	Lacticaseibacillus casei	IC50 (µMol)	0.0277	0.0090	1.9324	8.8000	AID211789; AID211791; AID211792; AID211793; AID211798; AID212842
Thymidylate synthase	Homo sapiens (human)	IC50 (µMol)	0.0680	0.0066	2.0637	9.5000	AID211083; AID212167; AID212298; AID212302; AID282788; AID391732; AID671163
Thymidylate synthase	Homo sapiens (human)	Ki	0.0082	0.0001	0.3435	3.0000	AID212331; AID212460
Thymidylate synthase	Mus musculus (house mouse)	IC50 (µMol)	4.8283	0.0004	1.3226	10.0000	AID212474; AID212475; AID212488; AID212489; AID212636; AID212637; AID212638; AID212642
Thymidylate synthase	Mus musculus (house mouse)	Ki	0.0122	0.0034	1.7375	9.3000	AID212656; AID212662
Thymidylate synthase	Escherichia coli K-12	Ki	0.0950	0.0300	0.5415	4.7000	AID211817
Dihydrofolate reductase	Escherichia coli K-12	IC50 (µMol)	23.0000	0.0015	0.5512	6.8000	AID282786; AID391736
Thymidylate synthase	Rattus norvegicus (Norway rat)	IC50 (µMol)	0.3600	0.3600	0.5400	0.9000	AID212678
Bifunctional dihydrofolate reductase-thymidylate synthase	Toxoplasma gondii	IC50 (µMol)	0.2636	0.0006	1.0428	10.0000	AID282787; AID282790; AID391735; AID391737; AID671165
Trifunctional purine biosynthetic protein adenosine-3	Mus musculus (house mouse)	Ki	6.0000	6.0000	6.0000	6.0000	AID72872
Dihydrofolate reductase	Rattus norvegicus (Norway rat)	Ki	0.0745	0.0000	0.0249	0.0745	AID58145
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Thymidylate synthase	Escherichia coli	Kii	0.0052	0.0051	0.0668	0.1900	AID211431; AID211635
Thymidylate synthase	Escherichia coli	Kis	0.0030	0.0030	0.0030	0.0030	AID211432
Thymidylate synthase	Homo sapiens (human)	Kii	0.0105	0.0100	0.0277	0.0620	AID212463; AID212464
Thymidylate synthase	Homo sapiens (human)	Kis	0.0120	0.0120	0.0120	0.0120	AID212465
Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)	Km	49.2000	0.4000	4.5344	7.3000	AID71218
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
tetrahydrobiopterin biosynthetic process	Dihydrofolate reductase	Homo sapiens (human)
one-carbon metabolic process	Dihydrofolate reductase	Homo sapiens (human)
negative regulation of translation	Dihydrofolate reductase	Homo sapiens (human)
axon regeneration	Dihydrofolate reductase	Homo sapiens (human)
response to methotrexate	Dihydrofolate reductase	Homo sapiens (human)
dihydrofolate metabolic process	Dihydrofolate reductase	Homo sapiens (human)
tetrahydrofolate metabolic process	Dihydrofolate reductase	Homo sapiens (human)
tetrahydrofolate biosynthetic process	Dihydrofolate reductase	Homo sapiens (human)
folic acid metabolic process	Dihydrofolate reductase	Homo sapiens (human)
positive regulation of nitric-oxide synthase activity	Dihydrofolate reductase	Homo sapiens (human)
regulation of removal of superoxide radicals	Dihydrofolate reductase	Homo sapiens (human)
dTMP biosynthetic process	Thymidylate synthase	Homo sapiens (human)
dTTP biosynthetic process	Thymidylate synthase	Homo sapiens (human)
circadian rhythm	Thymidylate synthase	Homo sapiens (human)
response to xenobiotic stimulus	Thymidylate synthase	Homo sapiens (human)
response to toxic substance	Thymidylate synthase	Homo sapiens (human)
negative regulation of translation	Thymidylate synthase	Homo sapiens (human)
uracil metabolic process	Thymidylate synthase	Homo sapiens (human)
methylation	Thymidylate synthase	Homo sapiens (human)
response to progesterone	Thymidylate synthase	Homo sapiens (human)
response to vitamin A	Thymidylate synthase	Homo sapiens (human)
response to cytokine	Thymidylate synthase	Homo sapiens (human)
tetrahydrofolate interconversion	Thymidylate synthase	Homo sapiens (human)
response to ethanol	Thymidylate synthase	Homo sapiens (human)
response to organophosphorus	Thymidylate synthase	Homo sapiens (human)
developmental growth	Thymidylate synthase	Homo sapiens (human)
cartilage development	Thymidylate synthase	Homo sapiens (human)
response to glucocorticoid	Thymidylate synthase	Homo sapiens (human)
response to folic acid	Thymidylate synthase	Homo sapiens (human)
intestinal epithelial cell maturation	Thymidylate synthase	Homo sapiens (human)
DNA biosynthetic process	Thymidylate synthase	Homo sapiens (human)
liver regeneration	Thymidylate synthase	Homo sapiens (human)
dTMP biosynthetic process	Thymidylate synthase	Escherichia coli K-12
response to radiation	Thymidylate synthase	Escherichia coli K-12
dTMP biosynthetic process	Thymidylate synthase	Escherichia coli K-12
dTTP biosynthetic process	Thymidylate synthase	Escherichia coli K-12
regulation of translation	Thymidylate synthase	Escherichia coli K-12
nucleotide biosynthetic process	Thymidylate synthase	Escherichia coli K-12
methylation	Thymidylate synthase	Escherichia coli K-12
10-formyltetrahydrofolate biosynthetic process	Dihydrofolate reductase	Escherichia coli K-12
response to xenobiotic stimulus	Dihydrofolate reductase	Escherichia coli K-12
folic acid biosynthetic process	Dihydrofolate reductase	Escherichia coli K-12
one-carbon metabolic process	Dihydrofolate reductase	Escherichia coli K-12
response to methotrexate	Dihydrofolate reductase	Escherichia coli K-12
tetrahydrofolate biosynthetic process	Dihydrofolate reductase	Escherichia coli K-12
response to antibiotic	Dihydrofolate reductase	Escherichia coli K-12
dihydrofolate metabolic process	Dihydrofolate reductase	Escherichia coli K-12
folic acid metabolic process	Dihydrofolate reductase	Escherichia coli K-12
liver development	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
nucleobase-containing compound metabolic process	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
glutamate metabolic process	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
one-carbon metabolic process	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
folic acid-containing compound metabolic process	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
animal organ regeneration	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
folic acid metabolic process	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
tetrahydrofolylpolyglutamate biosynthetic process	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
mRNA regulatory element binding translation repressor activity	Dihydrofolate reductase	Homo sapiens (human)
mRNA binding	Dihydrofolate reductase	Homo sapiens (human)
dihydrofolate reductase activity	Dihydrofolate reductase	Homo sapiens (human)
folic acid binding	Dihydrofolate reductase	Homo sapiens (human)
NADPH binding	Dihydrofolate reductase	Homo sapiens (human)
sequence-specific mRNA binding	Dihydrofolate reductase	Homo sapiens (human)
NADP binding	Dihydrofolate reductase	Homo sapiens (human)
mRNA regulatory element binding translation repressor activity	Thymidylate synthase	Homo sapiens (human)
thymidylate synthase activity	Thymidylate synthase	Homo sapiens (human)
folic acid binding	Thymidylate synthase	Homo sapiens (human)
protein homodimerization activity	Thymidylate synthase	Homo sapiens (human)
sequence-specific mRNA binding	Thymidylate synthase	Homo sapiens (human)
magnesium ion binding	Thymidylate synthase	Escherichia coli K-12
RNA binding	Thymidylate synthase	Escherichia coli K-12
thymidylate synthase activity	Thymidylate synthase	Escherichia coli K-12
methyltransferase activity	Thymidylate synthase	Escherichia coli K-12
protein homodimerization activity	Thymidylate synthase	Escherichia coli K-12
dihydrofolate reductase activity	Dihydrofolate reductase	Escherichia coli K-12
protein binding	Dihydrofolate reductase	Escherichia coli K-12
folic acid binding	Dihydrofolate reductase	Escherichia coli K-12
oxidoreductase activity	Dihydrofolate reductase	Escherichia coli K-12
NADP binding	Dihydrofolate reductase	Escherichia coli K-12
methotrexate binding	Dihydrofolate reductase	Escherichia coli K-12
dihydrofolic acid binding	Dihydrofolate reductase	Escherichia coli K-12
NADP+ binding	Dihydrofolate reductase	Escherichia coli K-12
NADPH binding	Dihydrofolate reductase	Escherichia coli K-12
tetrahydrofolylpolyglutamate synthase activity	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
ATP binding	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
metal ion binding	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
mitochondrion	Dihydrofolate reductase	Homo sapiens (human)
cytosol	Dihydrofolate reductase	Homo sapiens (human)
mitochondrion	Dihydrofolate reductase	Homo sapiens (human)
cytosol	Dihydrofolate reductase	Mus musculus (house mouse)
nucleus	Thymidylate synthase	Homo sapiens (human)
cytoplasm	Thymidylate synthase	Homo sapiens (human)
mitochondrion	Thymidylate synthase	Homo sapiens (human)
mitochondrial inner membrane	Thymidylate synthase	Homo sapiens (human)
mitochondrial matrix	Thymidylate synthase	Homo sapiens (human)
cytosol	Thymidylate synthase	Homo sapiens (human)
mitochondrion	Thymidylate synthase	Homo sapiens (human)
cytosol	Thymidylate synthase	Homo sapiens (human)
cytoplasm	Thymidylate synthase	Escherichia coli K-12
cytosol	Thymidylate synthase	Escherichia coli K-12
cytosol	Thymidylate synthase	Escherichia coli K-12
cytosol	Dihydrofolate reductase	Escherichia coli K-12
cytosol	Dihydrofolate reductase	Escherichia coli K-12
mitochondrial inner membrane	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
mitochondrial matrix	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
cytosol	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
cytoplasm	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
mitochondrion	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
cytosol	Folylpolyglutamate synthase, mitochondrial	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (126)

Assay ID	Title	Year	Journal	Article
AID213149	Concentration required for 50% inhibition against thymidylate synthase of Streptococcus faecium	1983	Journal of medicinal chemistry, Apr, Volume: 26, Issue:4	Folate analogues. 21. Synthesis and antifolate and antitumor activities of N10-(cyanomethyl)-5,8-dideazafolic acid.
AID391736	Inhibition of Escherichia coli DHFR	2008	Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18	Potent dual thymidylate synthase and dihydrofolate reductase inhibitors: classical and nonclassical 2-amino-4-oxo-5-arylthio-substituted-6-methylthieno[2,3-d]pyrimidine antifolates.
AID43393	Growth inhibition against Human leukemic cell line(CCRF-CEM) after 1 hr	1995	Journal of medicinal chemistry, Oct-27, Volume: 38, Issue:22	5-Arylthio-substituted 2-amino-4-oxo-6-methylpyrrolo[2,3-d]pyrimidine antifolates as thymidylate synthase inhibitors and antitumor agents.
AID99481	Inhibition of the growth of methotrexate resistant L1210 leukemia/R 81 cells in culture	1989	Journal of medicinal chemistry, Apr, Volume: 32, Issue:4	Comparison of the biological effects of selected 5,8-dideazafolate analogues with their 2-desamino counterparts.
AID391735	Inhibition of Toxoplasma gondii thymidylate synthase	2008	Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18	Potent dual thymidylate synthase and dihydrofolate reductase inhibitors: classical and nonclassical 2-amino-4-oxo-5-arylthio-substituted-6-methylthieno[2,3-d]pyrimidine antifolates.
AID57442	Inverse relative potency against purified L1210 dihydrofolate reductase (DHFR)	1985	Journal of medicinal chemistry, Oct, Volume: 28, Issue:10	Quinazoline antifolates inhibiting thymidylate synthase: variation of the N10 substituent.
AID211444	Inhibitory concentration against Escherichia coli Thymidylate synthase (TS).	2000	Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16	Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID20936	Compound was tested for its solubility in 0.20 M aqueous NaH2PO4 initially at pH 7	1989	Journal of medicinal chemistry, Mar, Volume: 32, Issue:3	Quinazoline antifolate thymidylate synthase inhibitors: nitrogen, oxygen, sulfur, and chlorine substituents in the C2 position.
AID211791	Inhibition of thymidylate synthase in Lactobacillus casei	1989	Journal of medicinal chemistry, Jun, Volume: 32, Issue:6	Folate analogues. 32. Synthesis and biological evaluation of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid and related compounds.
AID201873	Compound was evaluated for inhibition of tumor cell growth in SW/480 cell line	1991	Journal of medicinal chemistry, Sep, Volume: 34, Issue:9	Folate analogues. 35. Synthesis and biological evaluation of 1-deaza, 3-deaza, and bridge-elongated analogues of N10-propargyl-5,8-dideazafolic acid.
AID671165	Inhibition of Toxoplasma gondii thymidylate synthase	2012	Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14	Novel tricyclic indeno[2,1-d]pyrimidines with dual antiangiogenic and cytotoxic activities as potent antitumor agents.
AID71218	Apparent kinetic constant of substrate activity for Hog liver Folyl-polyglutamate synthase	1991	Journal of medicinal chemistry, Sep, Volume: 34, Issue:9	Folate analogues. 35. Synthesis and biological evaluation of 1-deaza, 3-deaza, and bridge-elongated analogues of N10-propargyl-5,8-dideazafolic acid.
AID80815	Inhibition of growth of H35FF cells; c = Could not be measured	1989	Journal of medicinal chemistry, Jun, Volume: 32, Issue:6	Folate analogues. 32. Synthesis and biological evaluation of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid and related compounds.
AID57749	Evaluated for the inhibition of dihydrofolate reductase in Lactobacillus casei	1987	Journal of medicinal chemistry, Jul, Volume: 30, Issue:7	Folate analogues. 30. Synthesis and biological evaluation of N10-propargyl-5,8-dideaza-5,6,7,8-tetrahydrofolic acid and related compounds.
AID98342	Inhibition of cellular growth against mouse (L1210) deficient in thymidine kinase.	1991	Journal of medicinal chemistry, Jul, Volume: 34, Issue:7	Design of enzyme inhibitors using iterative protein crystallographic analysis.
AID56150	Concentration required for 50% inhibition against dihydrofolate reductase of Streptococcus faecium	1983	Journal of medicinal chemistry, Apr, Volume: 26, Issue:4	Folate analogues. 21. Synthesis and antifolate and antitumor activities of N10-(cyanomethyl)-5,8-dideazafolic acid.
AID57306	The compound was evaluated in vitro for inhibition of purified L1210 dihydrofolate reductase	1986	Journal of medicinal chemistry, Apr, Volume: 29, Issue:4	Quinazoline antifolates inhibiting thymidylate synthase: benzoyl ring modifications.
AID80816	Inhibition of growth of H35N cells	1989	Journal of medicinal chemistry, Jun, Volume: 32, Issue:6	Folate analogues. 32. Synthesis and biological evaluation of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid and related compounds.
AID211792	Inhibitory activity against thymidylate Synthase from Lactobacillus casei	1995	Journal of medicinal chemistry, Oct-27, Volume: 38, Issue:22	5-Arylthio-substituted 2-amino-4-oxo-6-methylpyrrolo[2,3-d]pyrimidine antifolates as thymidylate synthase inhibitors and antitumor agents.
AID58145	Compound was evaluated for the inhibition of partially purified rat liver Dihydrofolate reductase(DHFR) enzyme.	1989	Journal of medicinal chemistry, Apr, Volume: 32, Issue:4	Quinazoline antifolates inhibiting thymidylate synthase: 2-desamino derivatives with enhanced solubility and potency.
AID212672	Inverse relative potency for the inhibition of L1210 thymidylate synthase	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Quinazoline antifolates inhibiting thymidylate synthase: variation of the amino acid.
AID96663	Growth inhibition was evaluated for L1210 cells in culture	1985	Journal of medicinal chemistry, Oct, Volume: 28, Issue:10	Quinazoline antifolates inhibiting thymidylate synthase: variation of the N10 substituent.
AID212637	Inhibitory activity against thymidylate synthase	1985	Journal of medicinal chemistry, Oct, Volume: 28, Issue:10	Quinazoline antifolates inhibiting thymidylate synthase: variation of the N10 substituent.
AID211430	Inhibitory factor uM	1999	Journal of medicinal chemistry, Jun-17, Volume: 42, Issue:12	Phthalein derivatives as a new tool for selectivity in thymidylate synthase inhibition.
AID103440	Compound was evaluated for inhibition of tumor cell growth in MCF-7 cell line	1991	Journal of medicinal chemistry, Sep, Volume: 34, Issue:9	Folate analogues. 35. Synthesis and biological evaluation of 1-deaza, 3-deaza, and bridge-elongated analogues of N10-propargyl-5,8-dideazafolic acid.
AID391733	Inhibition of Escherichia coli thymidylate synthase	2008	Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18	Potent dual thymidylate synthase and dihydrofolate reductase inhibitors: classical and nonclassical 2-amino-4-oxo-5-arylthio-substituted-6-methylthieno[2,3-d]pyrimidine antifolates.
AID213148	Concentration required for 50% inhibition against thymidylate synthase of Lactobacillus casei	1983	Journal of medicinal chemistry, Apr, Volume: 26, Issue:4	Folate analogues. 21. Synthesis and antifolate and antitumor activities of N10-(cyanomethyl)-5,8-dideazafolic acid.
AID212302	Inhibitory concentration against recombinant human (rh) Thymidylate synthase (TS)	2000	Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16	Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID44029	Inhibition of cellular growth against human (CCRF-CEM) leukemias (ATCC) deficient in thymidine kinase.	1991	Journal of medicinal chemistry, Jul, Volume: 34, Issue:7	Design of enzyme inhibitors using iterative protein crystallographic analysis.
AID391734	Inhibition of human recombinant DHFR	2008	Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18	Potent dual thymidylate synthase and dihydrofolate reductase inhibitors: classical and nonclassical 2-amino-4-oxo-5-arylthio-substituted-6-methylthieno[2,3-d]pyrimidine antifolates.
AID212298	Inhibitory activity against thymidylate Synthase from human recombinant sources	1995	Journal of medicinal chemistry, Oct-27, Volume: 38, Issue:22	5-Arylthio-substituted 2-amino-4-oxo-6-methylpyrrolo[2,3-d]pyrimidine antifolates as thymidylate synthase inhibitors and antitumor agents.
AID202627	The compound was tested for its growth inhibitory activity against S180 cells.	1992	Journal of medicinal chemistry, Jan-24, Volume: 35, Issue:2	Synthesis and antifolate evaluation of the 10-propargyl derivatives of 5-deazafolic acid, 5-deazaaminopterin, and 5-methyl-5-deazaaminopterin.
AID212167	Inhibition of pure human thymidylate synthase from extract of Manca human lymphoma cells	1989	Journal of medicinal chemistry, Jun, Volume: 32, Issue:6	Folate analogues. 32. Synthesis and biological evaluation of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid and related compounds.
AID212475	Inhibitory activity against thymidylate synthase isolated from L1210 leukemia cells	1988	Journal of medicinal chemistry, Feb, Volume: 31, Issue:2	Inhibition of murine thymidylate synthase and human dihydrofolate reductase by 5,8-dideaza analogues of folic acid and aminopterin.
AID212656	Binding affinity was evaluated against thymidylate synthase	1985	Journal of medicinal chemistry, Oct, Volume: 28, Issue:10	Quinazoline antifolates inhibiting thymidylate synthase: variation of the N10 substituent.
AID98530	Compound was evaluated for inhibition dose required to inhibit the growth of L1210 cells in culture.	1989	Journal of medicinal chemistry, Apr, Volume: 32, Issue:4	Quinazoline antifolates inhibiting thymidylate synthase: 2-desamino derivatives with enhanced solubility and potency.
AID211635	Inhibition of Thymidylate synthase of Escherichia coli (Kii)	1991	Journal of medicinal chemistry, Jul, Volume: 34, Issue:7	Design of enzyme inhibitors using iterative protein crystallographic analysis.
AID391732	Inhibition of human thymidylate synthase	2008	Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18	Potent dual thymidylate synthase and dihydrofolate reductase inhibitors: classical and nonclassical 2-amino-4-oxo-5-arylthio-substituted-6-methylthieno[2,3-d]pyrimidine antifolates.
AID282790	Inhibition of Toxoplasma gondii thymidylate synthase	2005	Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23	Synthesis of N-{4-[(2,4-diamino-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid and N-{4-[(2-amino-4-oxo-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid as dual inhibitors of dihydrofol
AID230430	It is the ratio of apparent kinetic constant to that of relative maximum velocity	1991	Journal of medicinal chemistry, Sep, Volume: 34, Issue:9	Folate analogues. 35. Synthesis and biological evaluation of 1-deaza, 3-deaza, and bridge-elongated analogues of N10-propargyl-5,8-dideazafolic acid.
AID282788	Inhibition of human thymidylate synthase	2005	Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23	Synthesis of N-{4-[(2,4-diamino-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid and N-{4-[(2-amino-4-oxo-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid as dual inhibitors of dihydrofol
AID211793	Inhibitory activity against thymidylate synthase derived from Lactobacillus casei	1986	Journal of medicinal chemistry, Jul, Volume: 29, Issue:7	Folate analogues. 25. Synthesis and biological evaluation of N10-propargylfolic acid and its reduced derivatives.
AID211432	Inhibitory activity against Escherichia coli thymidylate synthase	1996	Journal of medicinal chemistry, Feb-16, Volume: 39, Issue:4	Structure-based design of lipophilic quinazoline inhibitors of thymidylate synthase.
AID212474	Inhibition of L1210 leukemia thymidylate synthase (TS) enzyme	1989	Journal of medicinal chemistry, Apr, Volume: 32, Issue:4	Comparison of the biological effects of selected 5,8-dideazafolate analogues with their 2-desamino counterparts.
AID21332	Solubility at pH 7.4	1989	Journal of medicinal chemistry, Apr, Volume: 32, Issue:4	Quinazoline antifolates inhibiting thymidylate synthase: 2-desamino derivatives with enhanced solubility and potency.
AID99380	Antimicrobial activity against Lactobacillus casei MTX-resistant strain	1987	Journal of medicinal chemistry, Jul, Volume: 30, Issue:7	Folate analogues. 30. Synthesis and biological evaluation of N10-propargyl-5,8-dideaza-5,6,7,8-tetrahydrofolic acid and related compounds.
AID212842	Inhibitory concentration of compound to inhibit Thymidylate synthase (TS) in L1210 cells at conc. of 200 uM	1989	Journal of medicinal chemistry, Apr, Volume: 32, Issue:4	Quinazoline antifolates inhibiting thymidylate synthase: 2-desamino derivatives with enhanced solubility and potency.
AID72872	Inhibition of GAR transformylase isolated from murine lymphoma cell line L5178Y	1987	Journal of medicinal chemistry, Jul, Volume: 30, Issue:7	N10-substituted 5,8-dideazafolate inhibitors of glycinamide ribonucleotide transformylase.
AID57755	Inhibitory activity against dihydrofolate reductase derived from Lactobacillus casei	1986	Journal of medicinal chemistry, Jul, Volume: 29, Issue:7	Folate analogues. 25. Synthesis and biological evaluation of N10-propargylfolic acid and its reduced derivatives.
AID99391	Concentration required for 50% inhibition against Lactobacillus casei (ATCC 7469)	1983	Journal of medicinal chemistry, Apr, Volume: 26, Issue:4	Folate analogues. 21. Synthesis and antifolate and antitumor activities of N10-(cyanomethyl)-5,8-dideazafolic acid.
AID212678	Inhibitory concentration against rat Thymidylate synthase (TS)	2000	Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16	Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID211082	Compound was evaluated for the inhibition of Escherichia coli Thymidylate Synthase	1991	Journal of medicinal chemistry, Sep, Volume: 34, Issue:9	Folate analogues. 35. Synthesis and biological evaluation of 1-deaza, 3-deaza, and bridge-elongated analogues of N10-propargyl-5,8-dideazafolic acid.
AID72900	Inhibition of GC3/M TK- (human adenocarcinoma) cell growth in vitro.	1996	Journal of medicinal chemistry, Feb-16, Volume: 39, Issue:4	Structure-based design of lipophilic quinazoline inhibitors of thymidylate synthase.
AID212489	Evaluated for the inhibition of thymidylate synthesis in intact L1210 cells	1987	Journal of medicinal chemistry, Jul, Volume: 30, Issue:7	Folate analogues. 30. Synthesis and biological evaluation of N10-propargyl-5,8-dideaza-5,6,7,8-tetrahydrofolic acid and related compounds.
AID212642	The compound was not tested for inhibition of L1210 Thymidylate synthase due to insolubility	1990	Journal of medicinal chemistry, Jul, Volume: 33, Issue:7	Potent inhibition of thymidylate synthase by two series of nonclassical quinazolines.
AID671164	Inhibition of Escherichia coli thymidylate synthase	2012	Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14	Novel tricyclic indeno[2,1-d]pyrimidines with dual antiangiogenic and cytotoxic activities as potent antitumor agents.
AID212638	Inhibitory activity against thymidylate synthase in the intact L1210 cells	1986	Journal of medicinal chemistry, Jul, Volume: 29, Issue:7	Folate analogues. 25. Synthesis and biological evaluation of N10-propargylfolic acid and its reduced derivatives.
AID20935	Compound was tested for its solubility in 0.01 M aqueous NaH2PO4 initially at pH 7	1989	Journal of medicinal chemistry, Mar, Volume: 32, Issue:3	Quinazoline antifolate thymidylate synthase inhibitors: nitrogen, oxygen, sulfur, and chlorine substituents in the C2 position.
AID282785	Inhibition of human DHFR	2005	Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23	Synthesis of N-{4-[(2,4-diamino-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid and N-{4-[(2-amino-4-oxo-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid as dual inhibitors of dihydrofol
AID21328	Solubility at pH 5	1989	Journal of medicinal chemistry, Apr, Volume: 32, Issue:4	Quinazoline antifolates inhibiting thymidylate synthase: 2-desamino derivatives with enhanced solubility and potency.
AID57301	Inhibitory activity against dihydrofolate reductase	1985	Journal of medicinal chemistry, Oct, Volume: 28, Issue:10	Quinazoline antifolates inhibiting thymidylate synthase: variation of the N10 substituent.
AID99397	Inhibitory activity against Lactobacillus casei MTX-resistant	1986	Journal of medicinal chemistry, Jul, Volume: 29, Issue:7	Folate analogues. 25. Synthesis and biological evaluation of N10-propargylfolic acid and its reduced derivatives.
AID98693	Inhibitory dose for L1210 cells in culture. Not tested at higher concentrations because of their limited solubility	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Quinazoline antifolates inhibiting thymidylate synthase: variation of the amino acid.
AID98506	The compound was evaluated for the inhibition of growth of L1210 cells in culture	1986	Journal of medicinal chemistry, Apr, Volume: 29, Issue:4	Quinazoline antifolates inhibiting thymidylate synthase: benzoyl ring modifications.
AID227748	Inverse relative potency for inhibition of thymidylate synthase was measured as the ratio between IC50 value and IC50 value of compound 1a	1986	Journal of medicinal chemistry, Apr, Volume: 29, Issue:4	Quinazoline antifolates inhibiting thymidylate synthase: benzoyl ring modifications.
AID212125	Inhibitory factor against Pneumocystis carinii Thymidylate synthase at 27 uM	1999	Journal of medicinal chemistry, Jun-17, Volume: 42, Issue:12	Phthalein derivatives as a new tool for selectivity in thymidylate synthase inhibition.
AID671163	Inhibition of human thymidylate synthase	2012	Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14	Novel tricyclic indeno[2,1-d]pyrimidines with dual antiangiogenic and cytotoxic activities as potent antitumor agents.
AID212465	Inhibitory activity against human thymidylate synthase	1996	Journal of medicinal chemistry, Feb-16, Volume: 39, Issue:4	Structure-based design of lipophilic quinazoline inhibitors of thymidylate synthase.
AID209416	Antimicrobial activity against Streptococcus faecium strain ATCC 8043	1987	Journal of medicinal chemistry, Jul, Volume: 30, Issue:7	Folate analogues. 30. Synthesis and biological evaluation of N10-propargyl-5,8-dideaza-5,6,7,8-tetrahydrofolic acid and related compounds.
AID57445	Binding affinity was evaluated against dihydrofolate reductase	1985	Journal of medicinal chemistry, Oct, Volume: 28, Issue:10	Quinazoline antifolates inhibiting thymidylate synthase: variation of the N10 substituent.
AID209430	Concentration required for 50% inhibition against Streptococcus faecium (ATCC 8043)	1983	Journal of medicinal chemistry, Apr, Volume: 26, Issue:4	Folate analogues. 21. Synthesis and antifolate and antitumor activities of N10-(cyanomethyl)-5,8-dideazafolic acid.
AID99482	Inhibition of the growth of methotrexate sensitive L1210 leukemia/S cells in culture	1989	Journal of medicinal chemistry, Apr, Volume: 32, Issue:4	Comparison of the biological effects of selected 5,8-dideazafolate analogues with their 2-desamino counterparts.
AID212673	Tested for inhibition of thymidylate synthase from L1210 mouse leukemia cells expressed as ratio of I50 of compound to I50 of 1a (IRP= inverse relative potency)	1989	Journal of medicinal chemistry, Mar, Volume: 32, Issue:3	Quinazoline antifolate thymidylate synthase inhibitors: nitrogen, oxygen, sulfur, and chlorine substituents in the C2 position.
AID57751	Inhibition of dihydrofolate reductase in Lactobacillus casei	1989	Journal of medicinal chemistry, Jun, Volume: 32, Issue:6	Folate analogues. 32. Synthesis and biological evaluation of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid and related compounds.
AID211798	Inhibitory concentration against Lactobacillus casei Thymidylate synthase (TS).	2000	Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16	Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID211789	Evaluated for the inhibition of thymidylate synthase in Lactobacillus casei	1987	Journal of medicinal chemistry, Jul, Volume: 30, Issue:7	Folate analogues. 30. Synthesis and biological evaluation of N10-propargyl-5,8-dideaza-5,6,7,8-tetrahydrofolic acid and related compounds.
AID209418	Antimicrobial activity against Streptococcus faecium strain, MTX-resistant	1987	Journal of medicinal chemistry, Jul, Volume: 30, Issue:7	Folate analogues. 30. Synthesis and biological evaluation of N10-propargyl-5,8-dideaza-5,6,7,8-tetrahydrofolic acid and related compounds.
AID209434	Inhibitory activity against Streptococcus faecium ATCC 8043	1986	Journal of medicinal chemistry, Jul, Volume: 29, Issue:7	Folate analogues. 25. Synthesis and biological evaluation of N10-propargylfolic acid and its reduced derivatives.
AID99392	Concentration required for 50% inhibition against Lactobacillus casei MTX resistant	1983	Journal of medicinal chemistry, Apr, Volume: 26, Issue:4	Folate analogues. 21. Synthesis and antifolate and antitumor activities of N10-(cyanomethyl)-5,8-dideazafolic acid.
AID96897	Growth inhibition of L1210 cells without thymidine was determined	1990	Journal of medicinal chemistry, Jul, Volume: 33, Issue:7	Potent inhibition of thymidylate synthase by two series of nonclassical quinazolines.
AID212331	Binding affinity against human thymidylate synthase	1991	Journal of medicinal chemistry, Feb, Volume: 34, Issue:2	The renewed potential for folate antagonists in contemporary cancer chemotherapy.
AID212488	Evaluated for the inhibition of thymidylate synthase in permeabilised L1210 cells	1987	Journal of medicinal chemistry, Jul, Volume: 30, Issue:7	Folate analogues. 30. Synthesis and biological evaluation of N10-propargyl-5,8-dideaza-5,6,7,8-tetrahydrofolic acid and related compounds.
AID90486	Inhibition of growth of tumor cells, manca human lymphoma cells	1989	Journal of medicinal chemistry, Jun, Volume: 32, Issue:6	Folate analogues. 32. Synthesis and biological evaluation of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid and related compounds.
AID94410	Inhibition of murine L1210 cell line tissue culture growth	1996	Journal of medicinal chemistry, Feb-16, Volume: 39, Issue:4	Structure-based design of lipophilic quinazoline inhibitors of thymidylate synthase.
AID99381	Antimicrobial activity against Lactobacillus casei strain ATCC 7469	1987	Journal of medicinal chemistry, Jul, Volume: 30, Issue:7	Folate analogues. 30. Synthesis and biological evaluation of N10-propargyl-5,8-dideaza-5,6,7,8-tetrahydrofolic acid and related compounds.
AID202626	Concentration required for 50% inhibition against S180 cells	1983	Journal of medicinal chemistry, Apr, Volume: 26, Issue:4	Folate analogues. 21. Synthesis and antifolate and antitumor activities of N10-(cyanomethyl)-5,8-dideazafolic acid.
AID99396	Inhibitory activity against Lactobacillus casei ATCC 7469	1986	Journal of medicinal chemistry, Jul, Volume: 29, Issue:7	Folate analogues. 25. Synthesis and biological evaluation of N10-propargylfolic acid and its reduced derivatives.
AID209435	Inhibitory activity against Streptococcus faecium MTX-resistant	1986	Journal of medicinal chemistry, Jul, Volume: 29, Issue:7	Folate analogues. 25. Synthesis and biological evaluation of N10-propargylfolic acid and its reduced derivatives.
AID98166	Concentration required for 50% inhibition against L1210 cells	1983	Journal of medicinal chemistry, Apr, Volume: 26, Issue:4	Folate analogues. 21. Synthesis and antifolate and antitumor activities of N10-(cyanomethyl)-5,8-dideazafolic acid.
AID98507	Tested for 50% inhibition of L1210 cell growth in vitro	1990	Journal of medicinal chemistry, Jul, Volume: 33, Issue:7	Potent inhibition of thymidylate synthase by two series of nonclassical quinazolines.
AID82985	The compound was tested for its growth inhibitory activity against HL60 cells.	1992	Journal of medicinal chemistry, Jan-24, Volume: 35, Issue:2	Synthesis and antifolate evaluation of the 10-propargyl derivatives of 5-deazafolic acid, 5-deazaaminopterin, and 5-methyl-5-deazaaminopterin.
AID56813	Inhibitory activity against dihydrofolate reductase (DHFR) obtained from human WIL2 cells	1988	Journal of medicinal chemistry, Feb, Volume: 31, Issue:2	Inhibition of murine thymidylate synthase and human dihydrofolate reductase by 5,8-dideaza analogues of folic acid and aminopterin.
AID212651	Inverse relative potency against purified L1210 thymidylate synthase (TS)	1985	Journal of medicinal chemistry, Oct, Volume: 28, Issue:10	Quinazoline antifolates inhibiting thymidylate synthase: variation of the N10 substituent.
AID107970	Compound was evaluated for inhibition of tumor cell growth in Manca human lymphoma cell line	1991	Journal of medicinal chemistry, Sep, Volume: 34, Issue:9	Folate analogues. 35. Synthesis and biological evaluation of 1-deaza, 3-deaza, and bridge-elongated analogues of N10-propargyl-5,8-dideazafolic acid.
AID211431	Inhibitory activity against Escherichia coli thymidylate synthase	1996	Journal of medicinal chemistry, Feb-16, Volume: 39, Issue:4	Structure-based design of lipophilic quinazoline inhibitors of thymidylate synthase.
AID282786	Inhibition of Escherichia coli DHFR	2005	Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23	Synthesis of N-{4-[(2,4-diamino-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid and N-{4-[(2-amino-4-oxo-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid as dual inhibitors of dihydrofol
AID282787	Inhibition of Toxoplasma gondii DHFR	2005	Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23	Synthesis of N-{4-[(2,4-diamino-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid and N-{4-[(2-amino-4-oxo-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid as dual inhibitors of dihydrofol
AID56149	Concentration required for 50% inhibition against dihydrofolate reductase of Lactobacillus casei	1983	Journal of medicinal chemistry, Apr, Volume: 26, Issue:4	Folate analogues. 21. Synthesis and antifolate and antitumor activities of N10-(cyanomethyl)-5,8-dideazafolic acid.
AID25040	pH attained by the compound at saturation after dissolving in 0.01 M aqueous NaH2PO4 initially at pH 7	1989	Journal of medicinal chemistry, Mar, Volume: 32, Issue:3	Quinazoline antifolate thymidylate synthase inhibitors: nitrogen, oxygen, sulfur, and chlorine substituents in the C2 position.
AID391738	Selectivity ratio of IC50 for human recombinant DHFR to IC50 for Toxoplasma gondii DHFR	2008	Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18	Potent dual thymidylate synthase and dihydrofolate reductase inhibitors: classical and nonclassical 2-amino-4-oxo-5-arylthio-substituted-6-methylthieno[2,3-d]pyrimidine antifolates.
AID99395	Inhibition of growth of Lactobacillus casei	1989	Journal of medicinal chemistry, Jun, Volume: 32, Issue:6	Folate analogues. 32. Synthesis and biological evaluation of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid and related compounds.
AID209431	Concentration required for 50% inhibition against Streptococcus faecium MTX resistant	1983	Journal of medicinal chemistry, Apr, Volume: 26, Issue:4	Folate analogues. 21. Synthesis and antifolate and antitumor activities of N10-(cyanomethyl)-5,8-dideazafolic acid.
AID25041	pH attained by the compound at saturation after dissolving in 0.20 M aqueous NaH2PO4 initially at pH 7	1989	Journal of medicinal chemistry, Mar, Volume: 32, Issue:3	Quinazoline antifolate thymidylate synthase inhibitors: nitrogen, oxygen, sulfur, and chlorine substituents in the C2 position.
AID282789	Inhibition of Escherichia coli thymidylate synthase	2005	Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23	Synthesis of N-{4-[(2,4-diamino-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid and N-{4-[(2-amino-4-oxo-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-L-glutamic acid as dual inhibitors of dihydrofol
AID391737	Inhibition of Toxoplasma gondii DHFR	2008	Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18	Potent dual thymidylate synthase and dihydrofolate reductase inhibitors: classical and nonclassical 2-amino-4-oxo-5-arylthio-substituted-6-methylthieno[2,3-d]pyrimidine antifolates.
AID80820	Inhibition of growth of H35R cells	1989	Journal of medicinal chemistry, Jun, Volume: 32, Issue:6	Folate analogues. 32. Synthesis and biological evaluation of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid and related compounds.
AID211083	Compound was evaluated for the inhibition of human Thymidylate Synthase	1991	Journal of medicinal chemistry, Sep, Volume: 34, Issue:9	Folate analogues. 35. Synthesis and biological evaluation of 1-deaza, 3-deaza, and bridge-elongated analogues of N10-propargyl-5,8-dideazafolic acid.
AID96896	Growth inhibition of L1210 cells with thymidine at a concentration of 10 uM was determined	1990	Journal of medicinal chemistry, Jul, Volume: 33, Issue:7	Potent inhibition of thymidylate synthase by two series of nonclassical quinazolines.
AID211806	Inhibitory factor against Lactobacillus casei Thymidylate synthase at 27 uM	1999	Journal of medicinal chemistry, Jun-17, Volume: 42, Issue:12	Phthalein derivatives as a new tool for selectivity in thymidylate synthase inhibition.
AID212460	Inhibition of human Thymidylate synthase (Ki)	1991	Journal of medicinal chemistry, Jul, Volume: 34, Issue:7	Design of enzyme inhibitors using iterative protein crystallographic analysis.
AID71229	Relative maximum velocity of substrate activity for Hog liver Folyl-polyglutamate synthase (relative to control of 50 uM aminopterin)	1991	Journal of medicinal chemistry, Sep, Volume: 34, Issue:9	Folate analogues. 35. Synthesis and biological evaluation of 1-deaza, 3-deaza, and bridge-elongated analogues of N10-propargyl-5,8-dideazafolic acid.
AID72899	Inhibition of cellular growth against human adenocarcinoma (GC3/M TK-) deficient in thymidine kinase.	1991	Journal of medicinal chemistry, Jul, Volume: 34, Issue:7	Design of enzyme inhibitors using iterative protein crystallographic analysis.
AID212310	Inhibition factor for Human Thymidylate synthase at 27 uM.	1999	Journal of medicinal chemistry, Jun-17, Volume: 42, Issue:12	Phthalein derivatives as a new tool for selectivity in thymidylate synthase inhibition.
AID56811	Inhibition of human WIL2/dihydrofolate reductase activity	1989	Journal of medicinal chemistry, Apr, Volume: 32, Issue:4	Comparison of the biological effects of selected 5,8-dideazafolate analogues with their 2-desamino counterparts.
AID66154	Concentration required for 50% inhibition against Ehrlich cells	1983	Journal of medicinal chemistry, Apr, Volume: 26, Issue:4	Folate analogues. 21. Synthesis and antifolate and antitumor activities of N10-(cyanomethyl)-5,8-dideazafolic acid.
AID211633	Inhibition of Thymidylate synthase of Escherichia coli (Ki)	1991	Journal of medicinal chemistry, Jul, Volume: 34, Issue:7	Design of enzyme inhibitors using iterative protein crystallographic analysis.
AID206372	Inhibition of growth of Staphylococcus faecium	1989	Journal of medicinal chemistry, Jun, Volume: 32, Issue:6	Folate analogues. 32. Synthesis and biological evaluation of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid and related compounds.
AID212662	Tested for inhibitory activity against thymidylate synthase of L1210 cells	2001	Bioorganic & medicinal chemistry letters, Dec-03, Volume: 11, Issue:23	Cyclopenta[g]quinazoline-based antifolates: the effect of the chirality at the 6-position on the inhibition of thymidylate synthase (TS).
AID57111	Tested for 50% inhibition of WI-L2 Dihydrofolate reductase	1990	Journal of medicinal chemistry, Jul, Volume: 33, Issue:7	Potent inhibition of thymidylate synthase by two series of nonclassical quinazolines.
AID211817	In vitro inhibition of Lactobacillus casei Thymidylate synthase.	1999	Journal of medicinal chemistry, Jun-17, Volume: 42, Issue:12	Phthalein derivatives as a new tool for selectivity in thymidylate synthase inhibition.
AID98512	The compound was tested for its growth inhibitory activity against L1210 cells	1992	Journal of medicinal chemistry, Jan-24, Volume: 35, Issue:2	Synthesis and antifolate evaluation of the 10-propargyl derivatives of 5-deazafolic acid, 5-deazaaminopterin, and 5-methyl-5-deazaaminopterin.
AID212464	Inhibition of human Thymidylate synthase (Kii)	1991	Journal of medicinal chemistry, Jul, Volume: 34, Issue:7	Design of enzyme inhibitors using iterative protein crystallographic analysis.
AID212463	Inhibitory activity against human thymidylate synthase	1996	Journal of medicinal chemistry, Feb-16, Volume: 39, Issue:4	Structure-based design of lipophilic quinazoline inhibitors of thymidylate synthase.
AID105505	Compound was evaluated for inhibition of MTX influx into MOLT-4 cells	1991	Journal of medicinal chemistry, Sep, Volume: 34, Issue:9	Folate analogues. 35. Synthesis and biological evaluation of 1-deaza, 3-deaza, and bridge-elongated analogues of N10-propargyl-5,8-dideazafolic acid.
AID212636	Inhibitory activity against the thymidylate synthase in the Permeabilized L1210 cells	1986	Journal of medicinal chemistry, Jul, Volume: 29, Issue:7	Folate analogues. 25. Synthesis and biological evaluation of N10-propargylfolic acid and its reduced derivatives.
AID98935	Tested for inhibition of L1210 mouse leukemia cell growth in culture	1989	Journal of medicinal chemistry, Mar, Volume: 32, Issue:3	Quinazoline antifolate thymidylate synthase inhibitors: nitrogen, oxygen, sulfur, and chlorine substituents in the C2 position.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	12 (48.00)	18.7374
1990's	8 (32.00)	18.2507
2000's	4 (16.00)	29.6817
2010's	1 (4.00)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	2 (8.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	23 (92.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
pd 153035 4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline: structure given in first source. PD-153035 : A member of the class of quinazolines carrying a 3-bromophenylamino substituent at position 4 and two methoxy substituents at positions 6 and 7.	2.07	1	aromatic amine; aromatic ether; bromobenzenes; quinazolines; secondary amino compound	EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; epidermal growth factor receptor antagonist
phenolphthalein Phenolphthalein: An acid-base indicator which is colorless in acid solution, but turns pink to red as the solution becomes alkaline. It is used medicinally as a cathartic.	2	1	phenols
pyrimethamine Maloprim: contains above 2 cpds	2.07	1	aminopyrimidine; monochlorobenzenes	antimalarial; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor
trimethoprim Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.	2.46	2	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
thymidine [no description available]	2.02	1	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
methotrexate [no description available]	3.86	12	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
n-(4-(n-((2,4-diaminofuro(2,3-d)pyrimidin-5-yl)methyl)amino)benzoyl)glutamic acid N-(4-(N-((2,4-diaminofuro(2,3-d)pyrimidin-5-yl)methyl)amino)benzoyl)glutamic acid: structure given in first source	2	1
aminopterin Aminopterin: A folic acid derivative used as a rodenticide that has been shown to be teratogenic.	2.42	2	dicarboxylic acid	EC 1.5.1.3 (dihydrofolate reductase) inhibitor; mutagen
erlotinib [no description available]	2.07	1	aromatic ether; quinazolines; secondary amino compound; terminal acetylenic compound	antineoplastic agent; epidermal growth factor receptor antagonist; protein kinase inhibitor
semaxinib semaxanib : An oxindole that is 3-methyleneoxindole in which one of the hydrogens of the methylene group is replaced by a 3,5-dimethylpyrrol-2-yl group.	2.07	1	olefinic compound; oxindoles; pyrroles	angiogenesis modulating agent; antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; vascular endothelial growth factor receptor antagonist
orantinib orantinib: an antiangiogenic agent. orantinib : An oxindole that is 3-methyleneoxindole in which one of the hydrogens of the methylene group is substituted by a 2-(2-carboxyethyl)-3,5-dimethylpyrrol-3-yl group. It is an ATP-competitive inhibitor of the tyrosine kinase activity of fibroblast growth factor receptor 1.	2.07	1
su 11248 [no description available]	2.07	1	monocarboxylic acid amide; pyrroles	angiogenesis inhibitor; antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; immunomodulator; neuroprotective agent; vascular endothelial growth factor receptor antagonist
su 4312 SU4312 : A member of the class of oxindoles that is 3-methyleneoxindole in which one of the hydrogens of the methylene group has been replaced by a p-(dimethylamino)phenyl group. SU 4312 is a vascular endothelial growth factor (VEGF) receptor protein tyrosine kinase 1/2 and platelet derived growth factor (PDGF) receptor inhibitor. It also inhibits the neuronal nitric oxide synthase (NOS) and exhibits neuroprotection against NO-mediated neurotoxicity.	2.07	1
hypoxanthine [no description available]	2.02	1	nucleobase analogue; oxopurine; purine nucleobase	fundamental metabolite
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	2.37	2	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
raltitrexed [no description available]	2.45	2	N-acyl-amino acid
pemetrexed pemetrexed disodium : An organic sodium salt that is the disodium salt of N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid. Inhibits thymidylate synthase (TS), 421 dihydrofolate reductase (DHFR), and glycinamide ribonucleotide formyltransferase (GARFT).	2.73	3	N-acyl-L-glutamic acid; pyrrolopyrimidine	antimetabolite; antineoplastic agent; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; EC 2.1.1.45 (thymidylate synthase) inhibitor; EC 2.1.2.2 (phosphoribosylglycinamide formyltransferase) inhibitor
cb 3717 [no description available]	2.02	1	N-acyl-L-glutamic acid
(5)n,(8)n-deaza-(10)-n-methylfolate [no description available]	2.37	2
5,6,7,8-tetrahydrofolic acid tetrahydrofolic acid : A group of heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with one or more L-glutamic acid units.. tetrahydrofolate : A folate obtained by deprotonation of any tetrahydrofolic acid.	1.97	1	tetrahydrofolic acid	Saccharomyces cerevisiae metabolite
ag 85 AG 85: structure given in first source	3.07	1
cb 3705 CB 3705: inhibitor of dihydrofolate reductase & thymidylate synthetase	1.97	1

Condition	Relationship Strength	Studies
Leukemia L 1210 [description not available]	3.58	9
Experimental Mammary Neoplasms [description not available]	1.98	1
Benign Neoplasms [description not available]	2.89	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.89	1
Breast Cancer [description not available]	1.97	1
Hepatocellular Carcinoma [description not available]	1.97	1
Cancer of Liver [description not available]	1.97	1
Germinoblastoma [description not available]	1.97	1
Breast Neoplasms Tumors or cancer of the human BREAST.	1.97	1
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	1.97	1
Liver Neoplasms Tumors or cancer of the LIVER.	1.97	1
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	1.97	1
Adenocarcinoma, Basal Cell [description not available]	1.99	1
Leucocythaemia [description not available]	1.99	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	1.99	1
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	1.99	1
B16 Melanoma [description not available]	2.07	1

n-(4(n-((2-amino-4-hydroxy-6-quinazolinyl)methyl)prop-2-ynylamino)benzoyl)-l-glutamic acid

Cross-References

Synonyms (22)

Protein Targets (14)

Inhibition Measurements

Other Measurements

Biological Processes (43)

Molecular Functions (20)

Ceullar Components (6)

Bioassays (126)

Research

Studies (25)

Study Types

n-(4(n-((2-amino-4-hydroxy-6-quinazolinyl)methyl)prop-2-ynylamino)benzoyl)-l-glutamic acid

Cross-References

Synonyms (22)

Protein Targets (14)

Inhibition Measurements

Other Measurements

Biological Processes (43)

Molecular Functions (20)

Ceullar Components (6)

Bioassays (126)

Research

Studies (25)

Study Types

Related Drugs (22)

Related Conditions (17)