Compounds > 3-deazaguanine
Page last updated: 2024-12-06

3-deazaguanine

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

Description

3-Deazaguanine, also known as pyrrolo[2,3-d]pyrimidine-4,6(5H,7H)-dione, is a synthetic purine analog that has been extensively studied for its biological effects. It is an inhibitor of purine biosynthesis and has been shown to have antiviral, antitumor, and immunomodulatory properties. The synthesis of 3-deazaguanine typically involves a multi-step process, starting from readily available starting materials. It is studied extensively due to its potential therapeutic applications. For instance, its antiviral activity has been demonstrated against various viruses, including HIV, herpes simplex virus, and influenza virus. Its antitumor properties have been observed in both in vitro and in vivo studies, suggesting potential applications in cancer therapy. Moreover, its immunomodulatory effects, such as its ability to stimulate the immune system, have generated interest for its use in treating autoimmune diseases.'

3-deazaguanine: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID55710
CHEMBL ID31882
SCHEMBL ID4184
MeSH IDM0056141

Synonyms (43)

Synonym
nsc-261726
NCIMECH_000664
NCI60_002090
3-dg
ci-809
dezaguanine
brn 0608942
nsc 261726
dezaguanina [spanish]
dezaguaninum [latin]
dezaguanine [usan:inn]
6-aminoimidazo(4,5-c)pyridin-4(5h)-one
ci 908
4h-imidazo(4,5-c)pyridin-4-one, 6-amino-1,5-dihydro-
D03754
dezaguanine (usan/inn)
NSC261726 ,
3-deazaguanine
41729-52-6
icn 4221
6-amino-1,5-dihydroimidazo[4,5-c]pyridin-4-one
6-amino-1,5-dihydro-4h-imidazo(4,5-c)pyridin-4-one
ci-908
CHEMBL31882 ,
pd-9069573
bdbm50022256
6-amino-1,5-dihydro-imidazo[4,5-c]pyridin-4-one
6-amino-3,5-dihydro-imidazo[4,5-c]pyridin-4-one
AKOS006274250
CCG-35869
dezaguanina
dezaguaninum
unii-9drb973hui
9drb973hui ,
6-amino-1,5-dihydro-4h-imidazo[4,5-c]pyridin-4-one
dezaguanine [who-dd]
dezaguanine [usan]
dezaguanine [inn]
SCHEMBL4184
DTXSID10194525
4h-imidazo[4,5-c]pyridin-4-one,6-amino-3,5-dihydro-
Q27272408
41729-52-6(dezaguanine); 87434-82-0 (dezaguanine mesylate)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Purine nucleoside phosphorylaseHomo sapiens (human)IC50 (µMol)77.00000.00351.49875.0000AID164911
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (17)

Processvia Protein(s)Taxonomy
inosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
urate biosynthetic processPurine nucleoside phosphorylaseHomo sapiens (human)
positive regulation of T cell proliferationPurine nucleoside phosphorylaseHomo sapiens (human)
positive regulation of alpha-beta T cell differentiationPurine nucleoside phosphorylaseHomo sapiens (human)
allantoin metabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
nucleobase-containing compound metabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
inosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
deoxyinosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
deoxyadenosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
purine ribonucleoside salvagePurine nucleoside phosphorylaseHomo sapiens (human)
IMP catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
nicotinamide riboside catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
immune responsePurine nucleoside phosphorylaseHomo sapiens (human)
nucleotide biosynthetic processPurine nucleoside phosphorylaseHomo sapiens (human)
response to xenobiotic stimulusPurine nucleoside phosphorylaseHomo sapiens (human)
positive regulation of interleukin-2 productionPurine nucleoside phosphorylaseHomo sapiens (human)
purine-containing compound salvagePurine nucleoside phosphorylaseHomo sapiens (human)
dAMP catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
nucleoside bindingPurine nucleoside phosphorylaseHomo sapiens (human)
purine nucleobase bindingPurine nucleoside phosphorylaseHomo sapiens (human)
purine-nucleoside phosphorylase activityPurine nucleoside phosphorylaseHomo sapiens (human)
protein bindingPurine nucleoside phosphorylaseHomo sapiens (human)
phosphate ion bindingPurine nucleoside phosphorylaseHomo sapiens (human)
identical protein bindingPurine nucleoside phosphorylaseHomo sapiens (human)
guanosine phosphorylase activityPurine nucleoside phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
extracellular regionPurine nucleoside phosphorylaseHomo sapiens (human)
cytoplasmPurine nucleoside phosphorylaseHomo sapiens (human)
cytosolPurine nucleoside phosphorylaseHomo sapiens (human)
secretory granule lumenPurine nucleoside phosphorylaseHomo sapiens (human)
extracellular exosomePurine nucleoside phosphorylaseHomo sapiens (human)
ficolin-1-rich granule lumenPurine nucleoside phosphorylaseHomo sapiens (human)
cytoplasmPurine nucleoside phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (58)

Assay IDTitleYearJournalArticle
AID218131The minimum inhibitory concentration required to reduce vaccinia virus induced cytopathogenicity in primary rabbit kidney cells by 50%1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Synthesis and biological evaluation of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine).
AID232802Toxic level was evaluated1984Journal of medicinal chemistry, Nov, Volume: 27, Issue:11
Synthesis and antiviral/antitumor activities of certain 3-deazaguanine nucleosides and nucleotides.
AID1241035Cytotoxicity against African green monkey CV1 cells2015Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17
2- and 3-Fluoro-3-deazaneplanocins, 2-fluoro-3-deazaaristeromycins, and 3-methyl-3-deazaneplanocin: Synthesis and antiviral properties.
AID140706Change in weight of mammary adenocarcinoma 16/C in B6C3F1 female mice by subcutaneous administration on day 91983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
synthesis and antitumor activity of 2-deoxyribofuranosides of 3-deazaguanine.
AID1133181Antiviral activity against Parainfluenza virus 3 infected in human KB cells assessed as inhibition of virus-induced cytopathic effect after 72 hrs relative to control1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID105640Compound was tested for inhibition of MOLT-4 cell growth using human lymphoblast cytotoxicity assay in the presence of 2''-deoxy guanosine, cytotoxicity determined by monitoring uptake of [3H]thymidine1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of 8-amino-3-deazaguanine via imidazole precursors. Antitumor activity and inhibition of purine nucleoside phosphorylase.
AID216538The minimum inhibitory concentration required to reduce VSV induced cytopathogenicity in primary rabbit kidney cells by 50%1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Synthesis and biological evaluation of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine).
AID1130489Antitumor activity against mouse Sarcoma 180 cells allografted in mouse assessed as reduction in tumor growth at 50 mg/kg, ip qd for 8 days measured one day after last treatment relative to control1979Journal of medicinal chemistry, Aug, Volume: 22, Issue:8
Synthesis of arabinofuranosyl derivatives of 3-deazaguanine.
AID204964The minimum inhibitory concentration required to reduce Sindbis virus induced cytopathogenicity in primary rabbit kidney cells by 50%1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Synthesis and biological evaluation of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine).
AID216380In vitro antiviral activity (virus ratings (VR)) determined by comparing CPE development in drug-treated cells (T) and Vesicular stomatitis virus control cells1984Journal of medicinal chemistry, Nov, Volume: 27, Issue:11
Synthesis and antiviral/antitumor activities of certain 3-deazaguanine nucleosides and nucleotides.
AID1133198Antimicrobial activity against Candida albicans at 0.4 umol/mL by broth microdilution method1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID1133179Antiviral activity against HSV2 infected in human KB cells assessed as inhibition of virus-induced cytopathic effect after 72 hrs relative to control1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID1130491Antitumor activity against mouse Sarcoma 180 cells allografted in mouse assessed as reduction in tumor growth at 12.5 mg/kg, ip qd for 8 days measured one day after last treatment relative to control1979Journal of medicinal chemistry, Aug, Volume: 22, Issue:8
Synthesis of arabinofuranosyl derivatives of 3-deazaguanine.
AID199174The minimum inhibitory concentration required to reduce reovirus type I induced cytopathogenicity in primary rabbit kidney cells by 50%1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Synthesis and biological evaluation of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine).
AID1130494Toxicity in mouse allografted with mouse Sarcoma 180 cells assessed as mortality at 25 mg/kg, ip qd for 8 days measured one day after last treatment relative to control1979Journal of medicinal chemistry, Aug, Volume: 22, Issue:8
Synthesis of arabinofuranosyl derivatives of 3-deazaguanine.
AID1133180Antiviral activity against Vaccinia virus infected in human KB cells assessed as inhibition of virus-induced cytopathic effect after 72 hrs relative to control1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID88275The minimum inhibitory concentration required to reduce HSV-1(KOS) induced cytopathogenicity in primary rabbit kidney cells by 50%1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Synthesis and biological evaluation of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine).
AID101090Compound was tested in vitro for antitumor activity against L1210 leukemia cells in the absence of 2'-deoxy guanosine1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of 8-amino-3-deazaguanine via imidazole precursors. Antitumor activity and inhibition of purine nucleoside phosphorylase.
AID85704In vitro antiviral activity (virus ratings (VR)) determined by comparing CPE development in drug-treated cells (T) and HSV-1 virus control cells1984Journal of medicinal chemistry, Nov, Volume: 27, Issue:11
Synthesis and antiviral/antitumor activities of certain 3-deazaguanine nucleosides and nucleotides.
AID1133201Antimicrobial activity against Microsporum canis at 0.4 umol/mL by broth microdilution method1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID1133187Antiviral activity against Influenza B virus Lee infected in Swiss-Webster mouse assessed as host mean survival days at 10 mg/kg, po qd for 9 days1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID88296The minimum inhibitory concentration required to reduce HSV-2 (G) induced cytopathogenicity in primary rabbit kidney cells by 50%1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Synthesis and biological evaluation of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine).
AID217967In vitro antiviral activity (virus ratings (VR)) determined by comparing CPE development in drug-treated cells (T) and Vaccinia virus control cells1984Journal of medicinal chemistry, Nov, Volume: 27, Issue:11
Synthesis and antiviral/antitumor activities of certain 3-deazaguanine nucleosides and nucleotides.
AID54500The minimum inhibitory concentration required to reduce Coxsackie virus type B4 induced cytopathogenicity in primary rabbit kidney cells by 50%1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Synthesis and biological evaluation of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine).
AID155593In vitro antiviral activity (virus ratings (VR)) determined by comparing CPE development in drug-treated cells (T) and Parainfluenza type 3 virus control cells1984Journal of medicinal chemistry, Nov, Volume: 27, Issue:11
Synthesis and antiviral/antitumor activities of certain 3-deazaguanine nucleosides and nucleotides.
AID133082Percentage growth inhibition of mammary adenocarcinoma 16/C in B6C3F1 female mice1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
synthesis and antitumor activity of 2-deoxyribofuranosides of 3-deazaguanine.
AID164911Compound was tested for inhibition of purine nucleoside phosphorylase using human erythro lysate1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of 8-amino-3-deazaguanine via imidazole precursors. Antitumor activity and inhibition of purine nucleoside phosphorylase.
AID1133199Antimicrobial activity against Escherichia coli at 0.0025 to 0.125 umol/mL by broth microdilution method1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID108464The minimum inhibitory concentration required to reduce measles virus induced cytopathogenicity in primary rabbit kidney cells by 50%1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Synthesis and biological evaluation of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine).
AID106498Compound was tested for inhibition of MGL-8 cell growth using human lymphoblast cytotoxicity assay in the absence of 2''-deoxy guanosine, cytotoxicity determined by monitoring uptake of [3H]thymidine1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of 8-amino-3-deazaguanine via imidazole precursors. Antitumor activity and inhibition of purine nucleoside phosphorylase.
AID1130488Antitumor activity against mouse Sarcoma 180 cells allografted in mouse assessed as reduction in tumor growth at 100 mg/kg, ip qd for 8 days measured one day after last treatment relative to control1979Journal of medicinal chemistry, Aug, Volume: 22, Issue:8
Synthesis of arabinofuranosyl derivatives of 3-deazaguanine.
AID1133182Antiviral activity against Rhinovirus type 13 infected in human KB cells assessed as inhibition of virus-induced cytopathic effect after 72 hrs relative to control1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID139573Animals with palpable tumors on day 17 after subcutaneous administration in 6 B6C3F1 female mice; 5/6 animals were with palpable tumors.1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
synthesis and antitumor activity of 2-deoxyribofuranosides of 3-deazaguanine.
AID1133203Antimicrobial activity against Staphylococcus aureus at 0.4 umol/mL by broth microdilution method1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID1133178Antiviral activity against HSV1 infected in human KB cells assessed as inhibition of virus-induced cytopathic effect after 72 hrs relative to control1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID1133177Antiviral activity against Adenovirus type 3 infected in human KB cells assessed as inhibition of virus-induced cytopathic effect after 72 hrs relative to control1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID1133202Antimicrobial activity against Pseudomonas aeruginosa at 0.4 umol/mL by broth microdilution method1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID138970Tumor weight of C3H mammary adenocarcinoma 16/C in B6C3F1 female mice at 80 mg/kg by subcutaneous administration on day 171983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
synthesis and antitumor activity of 2-deoxyribofuranosides of 3-deazaguanine.
AID154158In vitro antitumor activity in the culture media (that produced 50% inhibition of the P388 leukemia cell growth as compared to the untreated cells); Inhibition at 10E-41984Journal of medicinal chemistry, Nov, Volume: 27, Issue:11
Synthesis and antiviral/antitumor activities of certain 3-deazaguanine nucleosides and nucleotides.
AID1133193Inhibition of adenine nucleotide biosynthesis in human EAC assessed as [14C]hypoxanthine incorporation at 1 mM after 60 mins by TLC analysis1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID1133194Inhibition of guanine nucleotide biosynthesis in human EAC assessed as [14C]hypoxanthine incorporation at 1 mM after 60 mins by TLC analysis1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID44903Ability to inhibit growth of CHO cells was determined1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Synthesis and biological evaluation of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine).
AID155597The minimum inhibitory concentration required to reduce parainfluenza virus type 3 induced cytopathogenicity in primary rabbit kidney cells by 50%1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Synthesis and biological evaluation of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine).
AID96797In vitro antitumor activity in the culture media (that produced 50% inhibition of the L1210 leukemia cell growth as compared to the untreated cells)1984Journal of medicinal chemistry, Nov, Volume: 27, Issue:11
Synthesis and antiviral/antitumor activities of certain 3-deazaguanine nucleosides and nucleotides.
AID1130495Toxicity in mouse allografted with mouse Sarcoma 180 cells assessed as mortality at 12.5 mg/kg, ip qd for 8 days measured one day after last treatment relative to control1979Journal of medicinal chemistry, Aug, Volume: 22, Issue:8
Synthesis of arabinofuranosyl derivatives of 3-deazaguanine.
AID1133200Antimicrobial activity against Epidermophyton floccosum at 0.4 umol/mL by broth microdilution method1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID1133186Antiviral activity against Influenza B virus Lee infected in Swiss-Webster mouse assessed as host mean survival days at 40 mg/kg, po qd for 9 days1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID9462Ability to inhibit growth of AA-6 cells (a mutant cell line resistant to 8-azaadenine and lacks adenine phosphoryltransferase) was determined1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Synthesis and biological evaluation of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine).
AID1130492Toxicity in mouse allografted with mouse Sarcoma 180 cells assessed as mortality at 100 mg/kg, ip qd for 8 days measured one day after last treatment relative to control1979Journal of medicinal chemistry, Aug, Volume: 22, Issue:8
Synthesis of arabinofuranosyl derivatives of 3-deazaguanine.
AID98042Effective dose that produced 50% inhibition of L1210 Leukemia cell growth in culture1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
synthesis and antitumor activity of 2-deoxyribofuranosides of 3-deazaguanine.
AID1241026Antiviral activity against Measles virus infected in African green monkey CV1 cells after 3 days by neutral red dye-based plaque reduction assay2015Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17
2- and 3-Fluoro-3-deazaneplanocins, 2-fluoro-3-deazaaristeromycins, and 3-methyl-3-deazaneplanocin: Synthesis and antiviral properties.
AID1130493Toxicity in mouse allografted with mouse Sarcoma 180 cells assessed as mortality at 50 mg/kg, ip qd for 8 days measured one day after last treatment relative to control1979Journal of medicinal chemistry, Aug, Volume: 22, Issue:8
Synthesis of arabinofuranosyl derivatives of 3-deazaguanine.
AID106499Compound was tested for inhibition of MGL-8 cell growth using human lymphoblast cytotoxicity assay in the presence of 2''-deoxy guanosine, cytotoxicity determined by monitoring uptake of [3H]thymidine1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of 8-amino-3-deazaguanine via imidazole precursors. Antitumor activity and inhibition of purine nucleoside phosphorylase.
AID1133204Antimicrobial activity against Trichophyton mentagrophytes at 0.4 umol/mL by broth microdilution method1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID209036Ability to inhibit growth of TG-1 cells (a mutant cell line resistant to 6-thioguanine and lacks hypoxanthine-guanine phosphoribosyltransferase) was determined1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Synthesis and biological evaluation of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine).
AID162241The minimum inhibitory concentration required to reduce polio virus type I induced cytopathogenicity in primary rabbit kidney cells by 50%1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Synthesis and biological evaluation of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine).
AID105509Compound was tested for inhibition of MOLT-4 cell growth using human lymphoblast cytotoxicity assay in the absence of 2''-deoxy guanosine, cytotoxicity determined by monitoring uptake of [3H]thymidine1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis of 8-amino-3-deazaguanine via imidazole precursors. Antitumor activity and inhibition of purine nucleoside phosphorylase.
AID1130490Antitumor activity against mouse Sarcoma 180 cells allografted in mouse assessed as reduction in tumor growth at 25 mg/kg, ip qd for 8 days measured one day after last treatment relative to control1979Journal of medicinal chemistry, Aug, Volume: 22, Issue:8
Synthesis of arabinofuranosyl derivatives of 3-deazaguanine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (44)

TimeframeStudies, This Drug (%)All Drugs %
pre-199025 (56.82)18.7374
1990's8 (18.18)18.2507
2000's6 (13.64)29.6817
2010's5 (11.36)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (2.27%)5.53%
Reviews1 (2.27%)6.00%
Case Studies1 (2.27%)4.05%
Observational0 (0.00%)0.25%
Other41 (93.18%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adenine
[no description available]		2.39206-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
formic acid
formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.		2.3720monocarboxylic acidantibacterial agent;
astringent;
metabolite;
protic solvent;
solvent
cytosine
[no description available]		2.4820aminopyrimidine;
pyrimidine nucleobase;
pyrimidone		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
thymine
[no description available]		2.0310pyrimidine nucleobase;
pyrimidone		Escherichia coli metabolite;
human metabolite;
mouse metabolite
urea
pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.		2.0310isourea;
monocarboxylic acid amide;
one-carbon compound		Daphnia magna metabolite;
Escherichia coli metabolite;
fertilizer;
flour treatment agent;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
pleconaril
WIN 63843: structure given in first source		2.1310
thymidine
[no description available]		2.3920pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
uridine triphosphate
Uridine Triphosphate: Uridine 5'-(tetrahydrogen triphosphate). A uracil nucleotide containing three phosphate groups esterified to the sugar moiety.		2.0210pyrimidine ribonucleoside 5'-triphosphate;
uridine 5'-phosphate		Escherichia coli metabolite;
mouse metabolite
cytidine
[no description available]		2.3820cytidinesEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
tubercidin
Tubercidin: An antibiotic purine ribonucleoside that readily substitutes for adenosine in the biological system, but its incorporation into DNA and RNA has an inhibitory effect on the metabolism of these nucleic acids.. tubercidin : An N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus.		1.9610antibiotic antifungal agent;
N-glycosylpyrrolopyrimidine;
ribonucleoside		antimetabolite;
antineoplastic agent;
bacterial metabolite
arginine
Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.		2.4220arginine;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		biomarker;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical
3,4-dihydropyran
[no description available]		1.9510
2-chloroadenosine
5-chloroformycin A: structure given in first source		3.0710purine nucleoside
oxazoles
Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.		2.13101,3-oxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
thiazoles
[no description available]		1.98101,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
deoxycytidine
[no description available]		2.2110pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
cladribine
[no description available]		3.0710organochlorine compound;
purine 2'-deoxyribonucleoside		antineoplastic agent;
immunosuppressive agent
vidarabine
adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.		3.0710beta-D-arabinoside;
purine nucleoside		antineoplastic agent;
bacterial metabolite;
nucleoside antibiotic
silver
Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.		2.2110copper group element atom;
elemental silver		Escherichia coli metabolite
ribavirin
Rebetron: Rebetron is tradename		4.69901-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
lamivudine
[no description available]		2.1110monothioacetal;
nucleoside analogue;
oxacycle;
primary alcohol		allergen;
anti-HBV agent;
antiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor;
HIV-1 reverse transcriptase inhibitor;
prodrug
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		3.520adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
thiazolyl blue
thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.		1.9810organic bromide saltcolorimetric reagent;
dye
thymidine 5'-triphosphate
thymidine 5'-triphosphate: RN given refers to parent cpd. dTTP : A thymidine phosphate having a triphosphate group at the 5'-position.		1.9910pyrimidine 2'-deoxyribonucleoside 5'-triphosphate;
thymidine phosphate		Escherichia coli metabolite;
mouse metabolite
o-(6)-methylguanine
O-(6)-methylguanine: structure. 6-O-methylguanine : A methylguanine in which the methyl group is positioned on the oxygen at position 6. Formed in DNA by alkylation of the oxygen atom of guanine, most often by N-nitroso compounds and sometimes due to methylation by other compounds such as endogenous S-adenosylmethionine, it base-pairs to thymine rather than cytidine, causing a G:C to A:T transition in DNA.. methylguanine : A 2-aminopurine that is guanine bearing a single methyl substituent.		1.9910methylguaninemutagen
pirodavir
pirodavir: antipicornavirus agent; structure given in first source		2.1310
neplanocin a
neplanocin A: neplanocins are antitumor antibiotics & carbocyclic analogs of purine nucleosides from Ampullarilla regularis A11079; see also neplanocin B, neplanocin C, neplanocin D & neplanocin F; structure in first source; a potent inhibitor of S-adenosylhomocysteine hydrolase		3.0710
9-(2,3-dihydroxypropyl)adenine, (s)-isomer
[no description available]		1.9610
ribavirin 5'-diphosphate
ribavirin-5'-phosphate: RN given refers to 5'-phosphate cpd; structure. ribavirin 5'-monophosphate : A 1-ribosyltriazole that is ribavirin in which the hydroxy group at the 5'-position is replaced by a phosphonooxy group. It is the active metabolite of the antiviral agent ribavirin.		1.95101-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide;
ribose monophosphate		antiviral agent;
drug metabolite;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
human blood serum metabolite
9-(2,3-dihydroxypropyl)adenine
[no description available]		1.9610
3-deazaguanosine
3-deazaguanosine: structure		4.93120
mycophenolic acid
Mycophenolic Acid: Compound derived from Penicillium stoloniferum and related species. It blocks de novo biosynthesis of purine nucleotides by inhibition of the enzyme inosine monophosphate dehydrogenase (IMP DEHYDROGENASE). Mycophenolic acid exerts selective effects on the immune system in which it prevents the proliferation of T-CELLS, LYMPHOCYTES, and the formation of antibodies from B-CELLS. It may also inhibit recruitment of LEUKOCYTES to sites of INFLAMMATION.. mycophenolate : A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of mycophenolic acid.. mycophenolic acid : A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mofetil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.		1.96102-benzofurans;
gamma-lactone;
monocarboxylic acid;
phenols		anticoronaviral agent;
antimicrobial agent;
antineoplastic agent;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
environmental contaminant;
immunosuppressive agent;
mycotoxin;
Penicillium metabolite;
xenobiotic
tiazofurin
tiazofurin: RN given refers to (beta-D)-isomer; structure given in first source. tiazofurine : A C-glycosyl compound that is 1,3-thiazole-4-carboxamide in which the hydrogen at position 2 has been replaced by a beta-D-ribofuranosyl group. It is metabolised to thiazole-4-carboxamide adenine dinucleotide (TAD), a selective inhibitor of inosine monophosphate dehydrogenase (IMP dehydrogenase).		3.07101,3-thiazoles;
C-glycosyl compound;
monocarboxylic acid amide		antineoplastic agent;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
prodrug
carbodine
carbodine: RN given refers to (R-(1alpha,2beta,3beta,4alpha))-isomer		2.3820
thioguanine anhydrous
Thioguanine: An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.. tioguanine : A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia.		1.96102-aminopurinesanticoronaviral agent;
antimetabolite;
antineoplastic agent
viroxime
[no description available]		2.1310
phosphoramidite
phosphoramidite: structure in first source. phosphoramidite : A compound with the general formula (RO)2PNR2. Phosphoramidites can be regarded as phosphites that have an NR2 instead of an OH group, or as amides of phosphorous acid.		2.0310
oxadiazoles
Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.		2.1310
ribose
ribopyranose : The pyranose form of ribose.		2.3820D-ribose;
ribopyranose
oligonucleotides
[no description available]		2.2110
adenosine kinase
Adenosine Kinase: An enzyme that catalyzes the formation of ADP plus AMP from adenosine plus ATP. It can serve as a salvage mechanism for returning adenosine to nucleic acids. EC 2.7.1.20.		1.9610
piperidines
Piperidines: A family of hexahydropyridines.		2.1310
deoxyguanosine
[no description available]		2.4220purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
guanosine monophosphate
Guanosine Monophosphate: A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature.. guanosine 5'-monophosphate : A purine ribonucleoside 5'-monophosphate having guanine as the nucleobase.		2.6530guanosine 5'-phosphate;
purine ribonucleoside 5'-monophosphate		biomarker;
Escherichia coli metabolite;
metabolite;
mouse metabolite
guanosine triphosphate
Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.		2.3720guanosine 5'-phosphate;
purine ribonucleoside 5'-triphosphate		Escherichia coli metabolite;
mouse metabolite;
uncoupling protein inhibitor
guanine
[no description available]		7.463912-aminopurines;
oxopurine;
purine nucleobase		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
guanosine
ribonucleoside : Any nucleoside where the sugar component is D-ribose.		4.6790guanosines;
purines D-ribonucleoside		fundamental metabolite
hypoxanthine
[no description available]		1.9610nucleobase analogue;
oxopurine;
purine nucleobase		fundamental metabolite
inosine
[no description available]		1.9610inosines;
purines D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
ganciclovir
[no description available]		2.11102-aminopurines;
oxopurine		antiinfective agent;
antiviral drug
allopurinol
Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.		1.9610nucleobase analogue;
organic heterobicyclic compound		antimetabolite;
EC 1.17.3.2 (xanthine oxidase) inhibitor;
gout suppressant;
radical scavenger
azaguanine
Azaguanine: One of the early purine analogs showing antineoplastic activity. It functions as an antimetabolite and is easily incorporated into ribonucleic acids.. 8-azaguanine : A triazolopyrimidine that consists of 3,6-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidine bearing amino and oxo substituents at positions 5 and 7 respectively.		1.9610nucleobase analogue;
triazolopyrimidines		antimetabolite;
antineoplastic agent;
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor
allopurinol riboside
allopurinol riboside : A nucleoside analogue that is allopurinol with a beta-D-ribofuranosyl moiety at the 1-position.		1.9610nucleoside analoguemetabolite
thiopurinol ribonucleoside
[no description available]		1.9610
pyrazofurin
pirazofurin : A C-glycosyl compound that is 4-hydroxy-1H-pyrazole-5-carboxamide in which the hydrogen at position 3 has been replaced by a beta-D-ribofuranosyl group.		2.3820C-glycosyl compound;
pyrazoles		antimetabolite;
antimicrobial agent;
antineoplastic agent;
EC 4.1.1.23 (orotidine-5'-phosphate decarboxylase) inhibitor
8-aminoguanine
[no description available]		1.9610
formycins
Formycins: Pyrazolopyrimidine ribonucleosides isolated from Nocardia interforma. They are antineoplastic antibiotics with cytostatic properties.		1.9610
8-aminoguanosine
[no description available]		1.9610
ConditionIndicatedRelationship StrengthStudiesTrials
Sarcoma 180
An experimental sarcoma of mice.		01.9510
Carcinoma, Ehrlich Tumor
A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.		01.9510
Infections, Orthomyxoviridae
[description not available]		01.9510
Orthomyxoviridae Infections
Virus diseases caused by the ORTHOMYXOVIRIDAE.		01.9510
Leukemia L 1210
[description not available]		03.67100
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		01.9610
Adenocarcinoma, Basal Cell
[description not available]		02.6530
Experimental Mammary Neoplasms
[description not available]		02.3720
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		02.6530
Rhabdomyosarcoma
A malignant solid tumor arising from mesenchymal tissues which normally differentiate to form striated muscle. It can occur in a wide variety of sites. It is divided into four distinct types: pleomorphic, predominantly in male adults; alveolar (RHABDOMYOSARCOMA, ALVEOLAR), mainly in adolescents and young adults; embryonal (RHABDOMYOSARCOMA, EMBRYONAL), predominantly in infants and children; and botryoidal, also in young children. It is one of the most frequently occurring soft tissue sarcomas and the most common in children under 15. (From Dorland, 27th ed; Holland et al., Cancer Medicine, 3d ed, p2186; DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, pp1647-9)		02.1310
Infections, Staphylococcal
[description not available]		02.0610
Staphylococcal Infections
Infections with bacteria of the genus STAPHYLOCOCCUS.		02.0610
Infections, Reoviridae
[description not available]		01.9610
Acute Myelogenous Leukemia
[description not available]		01.9610
Leukemia, Myeloid, Acute
Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.		01.9610
Breast Cancer
[description not available]		01.9610
Experimental Leukemia
[description not available]		01.9610
Breast Neoplasms
Tumors or cancer of the human BREAST.		01.9610
Cardiac Failure
[description not available]		03.3611
Benign Neoplasms
[description not available]		03.3611
Heart Failure
A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.		03.3611
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.		03.3611
Cell Transformation, Viral
An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.		01.9710