Page last updated: 2024-12-06

2,4-diaminoquinazoline

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

2,4-Diaminoquinazoline is a heterocyclic compound with a quinazoline core structure. It is a key intermediate in the synthesis of various pharmaceuticals, including anti-cancer drugs like quinazoline-based tyrosine kinase inhibitors and antibacterial agents. 2,4-diaminoquinazoline exhibits a wide range of biological activities, including anti-inflammatory, analgesic, and anti-microbial properties. Its synthesis typically involves condensation reactions of aromatic amines with anthranilic acid or its derivatives. The compound's importance lies in its versatility as a building block for diverse therapeutic agents, making it a subject of ongoing research and development.'

Cross-References

ID SourceID
PubMed CID65087
CHEMBL ID268354
SCHEMBL ID269636
MeSH IDM0061275

Synonyms (32)

Synonym
nsc-403373
nsc403373
1899-48-5
bdbm14323
quinazoline-2,4-diamine
CHEMBL268354
A18375
q24 ,
2,4-diaminoquinazoline
(2-amino-quinazolin-4-yl)-amine
unii-r3ub0t78el
nsc 403373
r3ub0t78el ,
2,4-quinazolinediamine
FT-0609975
AM20030238
AKOS015897034
SCHEMBL269636
2,4-quinazolinediamine #
DTXSID20172415
mfcd00236032
quinazolinediamine
2,4-diaminoquinazoline, aldrichcpr
J-012262
Q27464672
F15693
AS-10743
sri 93
quinazoline, 2,4-diamino-
CS-W022949
EN300-7409167
Z840266032

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Some compounds also proved to be effective inhibitors of stimulated acid secretion in both the rat and dog when dosed intravenously."( Reversible inhibitors of the gastric (H+/K+)-ATPase. 5. Substituted 2,4-diaminoquinazolines and thienopyrimidines.
Blurton, P; Brown, TH; Ife, RJ; Keeling, DJ; Leach, CA; Meeson, ML; Parsons, ME; Theobald, CJ, 1995
)
0.53
" In a dose-response analysis, intranasal administration of 1 µg compound 31 together with an inactivated vaccine (0."( The efficacy of a 2,4-diaminoquinazoline compound as an intranasal vaccine adjuvant to protect against influenza A virus infection in vivo.
An, T; Han, SB; Jeong, EJ; Kim, H; Kim, M; Noh, K; Shin, JS, 2022
)
1.06
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Dihydrofolate reductase Bos taurus (cattle)IC50 (µMol)19,952.59960.00170.04350.1007AID56780
Cationic trypsinBos taurus (cattle)Ki1,466.66670.00001.07539.0000AID1797191
Dihydrofolate reductaseStaphylococcus aureusIC50 (µMol)1,000,000.00000.00220.19762.4000AID56007
Dihydrofolate reductaseEscherichia coli K-12IC50 (µMol)100,000.00000.00150.55126.8000AID57580
Tryptase beta-2Homo sapiens (human)Ki1,466.66670.00101.05323.7000AID1797191
Dihydrofolate reductaseRattus norvegicus (Norway rat)IC50 (µMol)21.87760.00060.35076.2000AID58160
m7GpppX diphosphataseHomo sapiens (human)IC50 (µMol)0.14260.00010.07130.1426AID1442738
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
one-carbon metabolic processDihydrofolate reductase Bos taurus (cattle)
response to methotrexateDihydrofolate reductase Bos taurus (cattle)
tetrahydrofolate metabolic processDihydrofolate reductase Bos taurus (cattle)
tetrahydrofolate biosynthetic processDihydrofolate reductase Bos taurus (cattle)
proteolysisCationic trypsinBos taurus (cattle)
digestionCationic trypsinBos taurus (cattle)
10-formyltetrahydrofolate biosynthetic processDihydrofolate reductaseEscherichia coli K-12
response to xenobiotic stimulusDihydrofolate reductaseEscherichia coli K-12
folic acid biosynthetic processDihydrofolate reductaseEscherichia coli K-12
one-carbon metabolic processDihydrofolate reductaseEscherichia coli K-12
response to methotrexateDihydrofolate reductaseEscherichia coli K-12
tetrahydrofolate biosynthetic processDihydrofolate reductaseEscherichia coli K-12
response to antibioticDihydrofolate reductaseEscherichia coli K-12
dihydrofolate metabolic processDihydrofolate reductaseEscherichia coli K-12
folic acid metabolic processDihydrofolate reductaseEscherichia coli K-12
proteolysisTryptase beta-2Homo sapiens (human)
nuclear-transcribed mRNA catabolic process, deadenylation-dependent decaym7GpppX diphosphataseHomo sapiens (human)
mRNA cis splicing, via spliceosomem7GpppX diphosphataseHomo sapiens (human)
mRNA methylguanosine-cap decappingm7GpppX diphosphataseHomo sapiens (human)
deadenylation-dependent decapping of nuclear-transcribed mRNAm7GpppX diphosphataseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (19)

Processvia Protein(s)Taxonomy
mRNA bindingDihydrofolate reductase Bos taurus (cattle)
dihydrofolate reductase activityDihydrofolate reductase Bos taurus (cattle)
endopeptidase activityCationic trypsinBos taurus (cattle)
serine-type endopeptidase activityCationic trypsinBos taurus (cattle)
protein bindingCationic trypsinBos taurus (cattle)
metal ion bindingCationic trypsinBos taurus (cattle)
serpin family protein bindingCationic trypsinBos taurus (cattle)
dihydrofolate reductase activityDihydrofolate reductaseEscherichia coli K-12
protein bindingDihydrofolate reductaseEscherichia coli K-12
folic acid bindingDihydrofolate reductaseEscherichia coli K-12
oxidoreductase activityDihydrofolate reductaseEscherichia coli K-12
NADP bindingDihydrofolate reductaseEscherichia coli K-12
methotrexate bindingDihydrofolate reductaseEscherichia coli K-12
dihydrofolic acid bindingDihydrofolate reductaseEscherichia coli K-12
NADP+ bindingDihydrofolate reductaseEscherichia coli K-12
NADPH bindingDihydrofolate reductaseEscherichia coli K-12
serine-type endopeptidase activityTryptase beta-2Homo sapiens (human)
protein bindingTryptase beta-2Homo sapiens (human)
serine-type peptidase activityTryptase beta-2Homo sapiens (human)
RNA 7-methylguanosine cap bindingm7GpppX diphosphataseHomo sapiens (human)
RNA exonuclease activitym7GpppX diphosphataseHomo sapiens (human)
protein bindingm7GpppX diphosphataseHomo sapiens (human)
identical protein bindingm7GpppX diphosphataseHomo sapiens (human)
5'-(N(7)-methyl 5'-triphosphoguanosine)-[mRNA] diphosphatase activitym7GpppX diphosphataseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
cytoplasmDihydrofolate reductase Bos taurus (cattle)
mitochondrionDihydrofolate reductase Bos taurus (cattle)
serine protease inhibitor complexCationic trypsinBos taurus (cattle)
cytosolDihydrofolate reductaseEscherichia coli K-12
cytosolDihydrofolate reductaseEscherichia coli K-12
collagen-containing extracellular matrixTryptase beta-2Homo sapiens (human)
extracellular spaceTryptase beta-2Homo sapiens (human)
nucleusm7GpppX diphosphataseHomo sapiens (human)
nucleoplasmm7GpppX diphosphataseHomo sapiens (human)
cytoplasmm7GpppX diphosphataseHomo sapiens (human)
mitochondrionm7GpppX diphosphataseHomo sapiens (human)
cytosolm7GpppX diphosphataseHomo sapiens (human)
nucleusm7GpppX diphosphataseHomo sapiens (human)
P-bodym7GpppX diphosphataseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (18)

Assay IDTitleYearJournalArticle
AID1442738Inhibition of human DcpS assessed as increase in SMN2 promoter activity2017Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7
Design of Potent mRNA Decapping Scavenger Enzyme (DcpS) Inhibitors with Improved Physicochemical Properties To Investigate the Mechanism of Therapeutic Benefit in Spinal Muscular Atrophy (SMA).
AID58160Inhibitory activity against dihydrofolate reductase of rat liver1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
Inhibition of dihydrofolate reductase: structure-activity correlations of quinazolines based upon molecular shape analysis.
AID26822Partition coefficient (logP)1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Antifolate and antibacterial activities of 5-substituted 2,4-diaminoquinazolines.
AID56780In vitro inhibition of Bovine liver dihydrofolate reductase.1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Antifolate and antibacterial activities of 5-substituted 2,4-diaminoquinazolines.
AID1305351Induction of self-induced amyloid beta 42 (unknown origin) aggregation measured for 24 hrs by thioflavin T-based fluorescence spectroscopic analysis2016ACS medicinal chemistry letters, May-12, Volume: 7, Issue:5
Structure-Activity Relationship Studies of Isomeric 2,4-Diaminoquinazolines on β-Amyloid Aggregation Kinetics.
AID1442739Inhibition of DHFR (unknown origin)2017Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7
Design of Potent mRNA Decapping Scavenger Enzyme (DcpS) Inhibitors with Improved Physicochemical Properties To Investigate the Mechanism of Therapeutic Benefit in Spinal Muscular Atrophy (SMA).
AID197852Antibacterial activity (10 e-6 log (1/MIC) towards Staphylococcus aureus1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Antifolate and antibacterial activities of 5-substituted 2,4-diaminoquinazolines.
AID667647Antiviral activity against Dengue virus 2 infected in BHK-D2RepT replicon systems assessed as inhibition of viral replication after 24 hrs by luciferase reporter gene assay2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Discovery and optimization of 2,4-diaminoquinazoline derivatives as a new class of potent dengue virus inhibitors.
AID56007In vitro inhibition of Staphylococcus aureus (NTCT6571A) Dihydrofolate reductase.1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Antifolate and antibacterial activities of 5-substituted 2,4-diaminoquinazolines.
AID58164Concentration required for inhibition of rat liver dihydrofolate reductase (DHFR)1983Journal of medicinal chemistry, Jul, Volume: 26, Issue:7
Combined distance geometry analysis of dihydrofolate reductase inhibition by quinazolines and triazines.
AID1175065Binding affinity to HIV-1 TAR RNA by Tat-TAR fluorimetric competition assay2014Bioorganic & medicinal chemistry letters, Dec-15, Volume: 24, Issue:24
Fragment based search for small molecule inhibitors of HIV-1 Tat-TAR.
AID1145385Inhibition of liver dihydrofolate reductase (unknown origin)1976Journal of medicinal chemistry, May, Volume: 19, Issue:5
Inhibition of dihydrofolate reductase. Structure-activity correlations of quinazolines.
AID63878Antibacterial activity (10 e-6 log (1/MIC) towards Escherichia coli1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Antifolate and antibacterial activities of 5-substituted 2,4-diaminoquinazolines.
AID25614Dissociation constant was determined using UV method1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Antifolate and antibacterial activities of 5-substituted 2,4-diaminoquinazolines.
AID57580In vitro inhibition of Escherichia coli (B41) Dihydrofolate reductase.1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Antifolate and antibacterial activities of 5-substituted 2,4-diaminoquinazolines.
AID1305350Induction of self-induced amyloid beta 40 (unknown origin) aggregation measured for 24 hrs by thioflavin T-based fluorescence spectroscopic analysis2016ACS medicinal chemistry letters, May-12, Volume: 7, Issue:5
Structure-Activity Relationship Studies of Isomeric 2,4-Diaminoquinazolines on β-Amyloid Aggregation Kinetics.
AID667648Cytotoxicity against hamster BHK cells2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Discovery and optimization of 2,4-diaminoquinazoline derivatives as a new class of potent dengue virus inhibitors.
AID1797191Enzyme Assay and Determination of the Inhibition Constants from Article 10.1021/bi060173m: \\Structure-guided design of peptide-based tryptase inhibitors.\\2006Biochemistry, May-16, Volume: 45, Issue:19
Structure-guided design of peptide-based tryptase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (52)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (15.38)18.7374
1990's8 (15.38)18.2507
2000's7 (13.46)29.6817
2010's24 (46.15)24.3611
2020's5 (9.62)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.90

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.90 (24.57)
Research Supply Index4.01 (2.92)
Research Growth Index4.91 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.90)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (3.70%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other52 (96.30%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]