Compounds > grl 02031
Page last updated: 2024-08-01 07:42:04

grl 02031

Description

GRL 02031: a protease inhibitor with anti-HIV1 activity; structure in first source [MeSH]

Cross-References

ID SourceID
PubMed CID5275815
CHEMBL ID502946
SCHEMBL ID12757964
MeSH IDM0535713

Synonyms (18)

Synonym
[(3as,5r,6ar)-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-5-yl] n-[(2s,3r)-3-hydroxy-4-[(4-methoxyphenyl)sulfonyl-[[(2r)-5-oxopyrrolidin-2-yl]methyl]amino]-1-phenylbutan-2-yl]carbamate
[(3as,5r,6ar)-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-5-yl] n-[(1s,2r)-1-benzyl-2-hydroxy-3-[(4-methoxyphenyl)sulfonyl-[[(2r)-5-oxopyrrolidin-2-yl]methyl]amino]propyl]carbamate
uic-02031
carbamic acid, [(1s,2r)-2-hydroxy-3-[[(4-methoxyphenyl)sulfonyl][[(2r)-5-oxo-2-pyrrolidinyl]methyl]amino]-1-(phenylmethyl)propyl]-, (3as,5r,6ar)-hexahydro-2h-cyclopenta[b]furan-5-yl ester
grl 02031
grl02031
bdbm31817
methyl-2-pyrrolidinone, 19b
grl-02031
(3as,5r,6ar)-hexahydro-2h-cyclopenta[b]furan-5-yl [(1s,2r)-1-benzyl-2-hydroxy-3-([(4-methoxyphenyl)sulfonyl]{[(2r)-5-oxopyrrolidin-2-yl]methyl}amino)propyl]carbamate
CHEMBL502946
3VF7
3VFA
3VFB
3VF5
3H5B
SCHEMBL12757964
Q27449802

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Chain A, HIV-1 proteaseHuman immunodeficiency virus type 1 (BRU ISOLATE)Ki0.0001AID977610
Chain B, HIV-1 proteaseHuman immunodeficiency virus type 1 (BRU ISOLATE)Ki0.0001AID977610
Gag-Pol polyproteinHuman immunodeficiency virus type 1 (BRU ISOLATE)Ki0.0001AID1799176
Protease Human immunodeficiency virus 1Ki0.0007AID667084; AID667085; AID667086; AID667087
Protease Human immunodeficiency virus 1Ki0.0004AID667083

Other Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Protease Human immunodeficiency virus 1K0.9600AID738152

Bioassays (32)

Assay IDTitleYearJournalArticle
AID375204Ratio of EC50 for multidrug-resistant HIV1 isolate TM to EC50 for wild type HIV1 isolate ERS104pre2009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID667090Resistance index, ratio of Ki for HIV1 protease L76V mutant to Ki for HIV1 wild type protease2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
ISSN: 1520-4804		Potent antiviral HIV-1 protease inhibitor GRL-02031 adapts to the structures of drug resistant mutants with its P1'-pyrrolidinone ring.
AID738150Inhibition of transferrin receptor-fused HIV1 protease Q7K, L10F, I13V, I15V, D30V, V32I, L33F, E35D, M36I, S37N, I47V, I54L, Q58E, I62V, L63P, A71V, I84V, N88D, L89T, L90M mutant autoprocessing expressed in Escherichia coli up to 100 uM by SDS-PAGE analy2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
ISSN: 1520-4804		Extreme multidrug resistant HIV-1 protease with 20 mutations is resistant to novel protease inhibitors with P1'-pyrrolidinone or P2-tris-tetrahydrofuran.
AID667083Inhibition of HIV1 wild type protease using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-Arg-NH2 as substrate after 5 mins by spectrophotometry2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
ISSN: 1520-4804		Potent antiviral HIV-1 protease inhibitor GRL-02031 adapts to the structures of drug resistant mutants with its P1'-pyrrolidinone ring.
AID375200Antiviral activity against multidrug-resistant HIV1 isolate TM infected in PHA-stimulated PBMC assessed as inhibition of p24 gap protein2009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID375214Antiviral activity against atazanavir-resistant HIV1 NL4-32009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID738153Binding affinity to HIV1 protease Q7K, L10F, I13V, I15V, D30V, V32I, L33F, E35D, M36I, S37N, I47V, I54L, Q58E, I62V, L63P, A71V, I84V, N88D, L89T, L90M mutant expressed in Escherichia coli BL21 (DE3) assessed as association constant by isothermal titratio2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
ISSN: 1520-4804		Extreme multidrug resistant HIV-1 protease with 20 mutations is resistant to novel protease inhibitors with P1'-pyrrolidinone or P2-tris-tetrahydrofuran.
AID375206Ratio of EC50 for multidrug-resistant HIV1 isolate C to EC50 for wild type HIV1 isolate ERS104pre2009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID375205Ratio of EC50 for multidrug-resistant HIV1 isolate MM to EC50 for wild type HIV1 isolate ERS104pre2009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID667086Inhibition of HIV1 protease N88D mutant using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-Arg-NH2 as substrate after 5 mins by spectrophotometry2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
ISSN: 1520-4804		Potent antiviral HIV-1 protease inhibitor GRL-02031 adapts to the structures of drug resistant mutants with its P1'-pyrrolidinone ring.
AID667092Resistance index, ratio of Ki for HIV1 protease N88D mutant to Ki for HIV1 wild type protease2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
ISSN: 1520-4804		Potent antiviral HIV-1 protease inhibitor GRL-02031 adapts to the structures of drug resistant mutants with its P1'-pyrrolidinone ring.
AID667085Inhibition of HIV1 protease V82A mutant using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-Arg-NH2 as substrate after 5 mins by spectrophotometry2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
ISSN: 1520-4804		Potent antiviral HIV-1 protease inhibitor GRL-02031 adapts to the structures of drug resistant mutants with its P1'-pyrrolidinone ring.
AID667089Resistance index, ratio of Ki for HIV1 protease I47V mutant to Ki for HIV1 wild type protease2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
ISSN: 1520-4804		Potent antiviral HIV-1 protease inhibitor GRL-02031 adapts to the structures of drug resistant mutants with its P1'-pyrrolidinone ring.
AID667091Resistance index, ratio of Ki for HIV1 protease V82A mutant to Ki for HIV1 wild type protease2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
ISSN: 1520-4804		Potent antiviral HIV-1 protease inhibitor GRL-02031 adapts to the structures of drug resistant mutants with its P1'-pyrrolidinone ring.
AID375199Antiviral activity against wild type HIV1 isolate ERS104pre infected in PHA-stimulated PBMC assessed as inhibition of p24 gap protein2009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID375210Antiviral activity against indinavir-resistant HIV1 NL4-32009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID375197Inhibition of HIV protease by fluorescence energy transfer assay2009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID375207Ratio of EC50 for multidrug-resistant HIV1 isolate G to EC50 for wild type HIV1 isolate ERS104pre2009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID375208Antiviral activity against saquinavir-resistant HIV1 NL4-32009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID667087Inhibition of HIV1 protease L76V mutant using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-Arg-NH2 as substrate after 5 mins by spectrophotometry2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
ISSN: 1520-4804		Potent antiviral HIV-1 protease inhibitor GRL-02031 adapts to the structures of drug resistant mutants with its P1'-pyrrolidinone ring.
AID375198Antiviral activity against HIV1 LAI in human MT2 cells by MTT assay2009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID375209Antiviral activity against amprenavir-resistant HIV1 NL4-32009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID375211Antiviral activity against nelfinavir-resistant HIV1 NL4-32009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID375212Antiviral activity against ritonavir-resistant HIV1 NL4-32009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID667084Inhibition of HIV1 protease I47V mutant using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-Arg-NH2 as substrate after 5 mins by spectrophotometry2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
ISSN: 1520-4804		Potent antiviral HIV-1 protease inhibitor GRL-02031 adapts to the structures of drug resistant mutants with its P1'-pyrrolidinone ring.
AID375201Antiviral activity against multidrug-resistant HIV1 isolate MM infected in PHA-stimulated PBMC assessed as inhibition of p24 gap protein2009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID375202Antiviral activity against multidrug-resistant HIV1 isolate C infected in PHA-stimulated PBMC assessed as inhibition of p24 gap protein2009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID375213Antiviral activity against lopinavir-resistant HIV1 NL4-32009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID738152Binding affinity to HIV1 protease Q7K, L10F, I13V, I15V, D30V, V32I, L33F, E35D, M36I, S37N, I47V, I54L, Q58E, I62V, L63P, A71V, I84V, N88D, L89T, L90M mutant expressed in Escherichia coli BL21 (DE3) assessed as dissociation constant by isothermal titrati2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
ISSN: 1520-4804		Extreme multidrug resistant HIV-1 protease with 20 mutations is resistant to novel protease inhibitors with P1'-pyrrolidinone or P2-tris-tetrahydrofuran.
AID375203Antiviral activity against multidrug-resistant HIV1 isolate G infected in PHA-stimulated PBMC assessed as inhibition of p24 gap protein2009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID1799176Protease Inhibition Assay from Article 10.1021/jm900303m: \\Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protei2009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
ISSN: 1520-4804		Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (33.33)29.6817
2010's3 (50.00)24.3611
2020's1 (16.67)2.80

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%
Other6 (100.00%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
amprenavir
2
carbamate ester;
sulfonamide;
tetrahydrofuryl ester		antiviral drug;
HIV protease inhibitor		2009201313.0medium000110
lopinavir
1
amphetamines;
dicarboxylic acid diamide		anticoronaviral agent;
antiviral drug;
HIV protease inhibitor		2009200915.0low000100
atazanavir
1
carbohydrazideantiviral drug;
HIV protease inhibitor		2013201311.0low000010
darunavir
3
carbamate ester;
furofuran;
sulfonamide		antiviral drug;
HIV protease inhibitor		2009201312.7medium000120
saquinavir
1
L-asparagine derivative;
quinolines		antiviral drug;
HIV protease inhibitor		2013201311.0low000010
indinavir sulfate
1
dicarboxylic acid diamide;
N-(2-hydroxyethyl)piperazine;
piperazinecarboxamide		HIV protease inhibitor2009200915.0low000100
g 52
1
2013201311.0high000010
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
carbamates
5
amino-acid anion2009202010.2high000140
tetrahydrofuran
1
cyclic ether;
oxolanes;
saturated organic heteromonocyclic parent;
volatile organic compound		polar aprotic solvent2013201311.0low000010
cyclopentane
1
cycloalkane;
cyclopentanes;
volatile organic compound		non-polar solvent2009200915.0low000100
amprenavir
1
carbamate ester;
sulfonamide;
tetrahydrofuryl ester		antiviral drug;
HIV protease inhibitor		2013201311.0low000010
darunavir
1
carbamate ester;
furofuran;
sulfonamide		antiviral drug;
HIV protease inhibitor		2013201311.0low000010
g 52
1
2013201311.0high000010
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
HIV Coinfection0
1
202020204.0high000010
HIV Infections0
1
202020204.0high000010