Compounds > 6-chloro-1,4-dihydro-4-oxo-1-(beta-d-ribofuranosyl)quinoline-3-carboxylic acid
Page last updated: 2024-11-08

6-chloro-1,4-dihydro-4-oxo-1-(beta-d-ribofuranosyl)quinoline-3-carboxylic acid

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

Description

6-chloro-1,4-dihydro-4-oxo-1-(beta-D-ribofuranosyl)quinoline-3-carboxylic acid: inhibits HSV-1 replication; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID485378
CHEMBL ID560455
SCHEMBL ID19583486
MeSH IDM0520126

Synonyms (7)

Synonym
6-chloro-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-oxo-quinoline-3-carboxylic acid
6-chloro-1,4-dihydro-4-oxo-1-(beta-d-ribofuranosyl)quinoline-3-carboxylic acid
6-chloro-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-oxoquinoline-3-carboxylic acid
CHEMBL560455 ,
bdbm50438272
SCHEMBL19583486
6-chloro-1,4-dihydro-4-oxo-1-(beta-d-ribofuranosyl) quinoline-3-carboxylic acid

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Compound 2j was identified as a lead compound for future investigation due to its: (i) high activity against HIV-1, (ii) low cytotoxicity in PBMC, (iii) low toxic risks based on in silico evaluation, (iv) a good theoretical oral bioavailability according to Lipinski 'rule of five', (v) higher druglikeness and drug-score values than current antivirals AZT and efavirenz."( Synthesis, antiviral activity and molecular modeling of oxoquinoline derivatives.
Abreu, P; Barbosa, JE; Batalha, PN; Bou-Habib, DC; Castro, HC; Cirne-Santos, CC; Cunha, AC; de Souza, MC; Ferreira, VF; Garrido, V; Giongo, V; Nogueira, CM; Paixão, IC; Rodrigues, CR; Santos, Fda C; Silva, Dde O; Simonetti, BR; Souza, TM; Temerozo, JR, 2009)		0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glyceraldehyde-3-phosphate dehydrogenase, glycosomalTrypanosoma cruziKi32.27002.00004.00006.0000AID762765
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Ki0.50000.00031.552310.0000AID671652
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID684322Ratio of inosine Km to compound Ki for Leishmania donovani recombinant nucleoside hydrolase2012European journal of medicinal chemistry, Oct, Volume: 56Kinetics and docking studies of two potential new inhibitors of the nucleoside hydrolase from Leishmania donovani.
AID671656Selectivity ratio of CC50 for human PBMC to EC50 for Human immunodeficiency virus 1 Ba-L2012Bioorganic & medicinal chemistry letters, Aug-01, Volume: 22, Issue:15
Oxoquinoline acyclonucleoside phosphonate analogues as a new class of specific inhibitors of human immunodeficiency virus type 1.
AID762750Effect on Saccharomyces cerevisiae TDH1 up to 500 uM2013Bioorganic & medicinal chemistry letters, Aug-15, Volume: 23, Issue:16
Molecular design, synthesis and biological evaluation of 1,4-dihydro-4-oxoquinoline ribonucleosides as TcGAPDH inhibitors with trypanocidal activity.
AID762763Competitive inhibition of Trypanosoma cruzi glycosomal GAPDH assessed as increase in NAD+ Km by ITC method (Rvb = 40.14 +/- 3.13 uM)2013Bioorganic & medicinal chemistry letters, Aug-15, Volume: 23, Issue:16
Molecular design, synthesis and biological evaluation of 1,4-dihydro-4-oxoquinoline ribonucleosides as TcGAPDH inhibitors with trypanocidal activity.
AID684321Inhibition of Leishmania donovani recombinant nucleoside hydrolase expressed in Escherichia coli DH5alpha coexpressing MBP using inosine as substrate by xanthine oxidase-coupled assay2012European journal of medicinal chemistry, Oct, Volume: 56Kinetics and docking studies of two potential new inhibitors of the nucleoside hydrolase from Leishmania donovani.
AID762762Competitive inhibition of Trypanosoma cruzi glycosomal GAPDH assessed as NAD+ Vmax by ITC method (Rvb = 0.24 +/- 0.01 uM/sec)2013Bioorganic & medicinal chemistry letters, Aug-15, Volume: 23, Issue:16
Molecular design, synthesis and biological evaluation of 1,4-dihydro-4-oxoquinoline ribonucleosides as TcGAPDH inhibitors with trypanocidal activity.
AID684323Competitive inhibition of Leishmania donovani recombinant nucleoside hydrolase expressed in Escherichia coli DH5alpha coexpressing MBP using inosine as substrate by Lineweaver-Burk plot analysis2012European journal of medicinal chemistry, Oct, Volume: 56Kinetics and docking studies of two potential new inhibitors of the nucleoside hydrolase from Leishmania donovani.
AID426888Inhibition of HIV1 viral replication infected in human PBMC cells assessed as viral p24Ag concentration after 7 days postinfection by ELISA relative to untreated control2009Bioorganic & medicinal chemistry, Aug-01, Volume: 17, Issue:15
Synthesis, antiviral activity and molecular modeling of oxoquinoline derivatives.
AID671652Inhibition of Human immunodeficiency virus 1 reverse transcriptase2012Bioorganic & medicinal chemistry letters, Aug-01, Volume: 22, Issue:15
Oxoquinoline acyclonucleoside phosphonate analogues as a new class of specific inhibitors of human immunodeficiency virus type 1.
AID426889Inhibition of HIV1 viral replication infected in human PBMC cells assessed as viral p24Ag concentration after 7 days postinfection by ELISA2009Bioorganic & medicinal chemistry, Aug-01, Volume: 17, Issue:15
Synthesis, antiviral activity and molecular modeling of oxoquinoline derivatives.
AID762749Effect on Saccharomyces cerevisiae TDH2 up to 500 uM2013Bioorganic & medicinal chemistry letters, Aug-15, Volume: 23, Issue:16
Molecular design, synthesis and biological evaluation of 1,4-dihydro-4-oxoquinoline ribonucleosides as TcGAPDH inhibitors with trypanocidal activity.
AID426891Selectivity index, ratio of CC50 for human PBMC cells to EC50 for HIV12009Bioorganic & medicinal chemistry, Aug-01, Volume: 17, Issue:15
Synthesis, antiviral activity and molecular modeling of oxoquinoline derivatives.
AID762765Competitive inhibition of Trypanosoma cruzi glycosomal GAPDH NAD+ binding site by ITC method2013Bioorganic & medicinal chemistry letters, Aug-15, Volume: 23, Issue:16
Molecular design, synthesis and biological evaluation of 1,4-dihydro-4-oxoquinoline ribonucleosides as TcGAPDH inhibitors with trypanocidal activity.
AID684324Inhibition of xanthine oxidase using hypoxanthine as substrate by UV-Vis spectrophotometry2012European journal of medicinal chemistry, Oct, Volume: 56Kinetics and docking studies of two potential new inhibitors of the nucleoside hydrolase from Leishmania donovani.
AID671651Antiviral activity against Human immunodeficiency virus 1 infected in human PBMC assessed as inhibition of viral replication2012Bioorganic & medicinal chemistry letters, Aug-01, Volume: 22, Issue:15
Oxoquinoline acyclonucleoside phosphonate analogues as a new class of specific inhibitors of human immunodeficiency virus type 1.
AID762748Effect on Saccharomyces cerevisiae TDH3 up to 500 uM2013Bioorganic & medicinal chemistry letters, Aug-15, Volume: 23, Issue:16
Molecular design, synthesis and biological evaluation of 1,4-dihydro-4-oxoquinoline ribonucleosides as TcGAPDH inhibitors with trypanocidal activity.
AID426890Cytotoxicity against human PBMC by XTT assay2009Bioorganic & medicinal chemistry, Aug-01, Volume: 17, Issue:15
Synthesis, antiviral activity and molecular modeling of oxoquinoline derivatives.
AID762757Cytotoxicity against Balb-c mouse 3T3 cells assessed as cell death at > 100 umol/L by MTT assay2013Bioorganic & medicinal chemistry letters, Aug-15, Volume: 23, Issue:16
Molecular design, synthesis and biological evaluation of 1,4-dihydro-4-oxoquinoline ribonucleosides as TcGAPDH inhibitors with trypanocidal activity.
AID671657Antiviral activity against Human immunodeficiency virus 1 Ba-L infected in macrophages assessed as inhibition of viral replication2012Bioorganic & medicinal chemistry letters, Aug-01, Volume: 22, Issue:15
Oxoquinoline acyclonucleoside phosphonate analogues as a new class of specific inhibitors of human immunodeficiency virus type 1.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (57.14)29.6817
2010's3 (42.86)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.36

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 Index12.36 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.44 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.36)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
benzonidazole
benzonidazole: used in treatment of Chagas' disease. benznidazole : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2-nitroimidazol-1-yl)acetic acid with the aromatic amino group of benzylamine. Used for treatment of Chagas disease.		2.0810C-nitro compound;
imidazoles;
monocarboxylic acid amide		antiprotozoal drug
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		2.4620azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
posaconazole
[no description available]		2.0810aromatic ether;
conazole antifungal drug;
N-arylpiperazine;
organofluorine compound;
oxolanes;
triazole antifungal drug;
triazoles		trypanocidal drug
acyclovir
Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.		2.04102-aminopurines;
oxopurine		antimetabolite;
antiviral drug
inosine
[no description available]		2.0710inosines;
purines D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
HIV Coinfection
[description not available]		02.4520
HIV Infections
Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).		02.4520