3,4,5-Trisubstituted-1,2,4-4H-triazoles as WT and Y188L mutant HIV-1 non-nucleoside reverse transcriptase inhibitors: Docking-based CoMFA and CoMSIA analyses

Journal of Molecular Modeling

Volumn 17, Issue 7, 2011, Pages 1537-1550

  Cichero, Elena ^a   Buffa, Laura ^a   Fossa, Paola ^a  

^a UNIVERSITY OF GENOA   (Italy)

Author keywords

CoMFA; CoMSIA; HIV 1; Reverse transcriptase; Triazoles; Y188L HIV 1 mutant

Indexed keywords

HYDROGEN; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; TRIAZOLE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; BINDING AFFINITY; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; DRUG STRUCTURE; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR DOCKING; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STATIC ELECTRICITY; SUBSTITUTION REACTION; WILD TYPE;

HIV REVERSE TRANSCRIPTASE; LIGANDS; MODELS, MOLECULAR; MUTANT PROTEINS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; REVERSE TRANSCRIPTASE INHIBITORS; TRIAZOLES;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 80051788965     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-010-0857-7     Document Type: Article

References (21)

1. H Jonckheere J Anne E De Clercq 2000 The HIV-1 reverse transcription (RT) process as target for RT inhibitors Med Res Rev 20 129 154 10.1002/(SICI)1098- 1128(200003)20:2<129::AID-MED2>3.0.CO;2-A 1:CAS:528:DC%2BD3cXitVeisLk%3D (Pubitemid 30134322)
2. E De Clercq 2001 New developments in anti-HIV chemotherapy Farmaco 56 3 12 10.1016/S0014-827X(01)01007-2 (Pubitemid 32372575)
3. E De Clercq 2005 Emerging anti-HIV drugs Expert Opin Emerg Drugs 10 241 273 10.1517/14728214.10.2.241 (Pubitemid 40695127)
4. E De Clercq 2005 New approaches toward anti-HIV chemotherapy E J Med Chem 48 1297 1313 10.1021/jm040158k (Pubitemid 40364540)
5. G Barbaro A Scozzafava A Mastrolorenzo CT Supuran 2005 Highly active antiretroviral therapy: current state of the art, new agents and their pharmacological interactions useful for improving therapeutic outcome Curr Pharm Des 11 1805 1843 10.2174/1381612053764869 1:CAS:528:DC%2BD2MXkt1Chur8%3D (Pubitemid 40668138)
6. J Balzarini 2004 Current status of the non-nucleoside reverse transcriptase inhibitors of human immunodeficiency virus type 1 Curr Top Med Chem 4 921 944 10.2174/1568026043388420 1:CAS:528:DC%2BD2cXjslGhtLo%3D (Pubitemid 38864691)
7. E De Clercq 1998 The role of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection Antiviral Res 38 153 179 10.1016/S0166-3542(98)00025-4 (Pubitemid 29065480)
8. OS Pedersen EB Pedersen 1999 Non-nucleoside reverse transcriptase inhibitors, the NNRTI boom Antivir Chem Chemother 10 285 314 1:CAS:528:DyaK1MXnvFKrt7w%3D
9. OS Pedersen EB Pedersen 2000 The flourishing syntheses of non-nucleoside reverse transcriptase inhibitors Synthesis 4 479 495 10.1055/s-2000-6357 (Pubitemid 30202195)
10. G Campiani A Ramunno G Maga V Nacci C Fattorusso B Catalanotti E Morelli E Novellino 2002 Non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors:past, present, and future perspectives Curr Pharm Des 8 615 657 10.2174/1381612024607207 1:CAS:528:DC%2BD38XivFynt7Y%3D (Pubitemid 34406406)
11. E De Clercq 2004 Non-nucleoside reverse transcriptase inhibitors (NNRTIs): past, present, and future Chem Biodiversity 1 44 64 10.1002/cbdv.200490012
12. R Pauwels 2004 New non-nucleoside reverse transcriptase inhibitors (NNRTIs) in development for the treatment of HIV infections Curr Opin Pharmacol 4 437 446 10.1016/j.coph.2004.07.005 1:CAS:528:DC%2BD2cXntlGhtL0%3D (Pubitemid 40533003)
13. AJ Leigh Brown SD Frost WC Mathews K Dawson NS Hellmann ES Daar DD Richman SJ Little 2003 Transmission fitness of drug-resistant human immunodeficiency virus and the prevalence of resistance in the antiretroviral-treated population J Infect Dis 187 683 686 10.1086/367989 (Pubitemid 36250034)
14. DD Richman SC Morton T Wrin N Hellmann S Berry MF Shapiro SA Bozzette 2004 The prevalence of antiretroviral drug resistance in the United States AIDS 18 1393 1401 10.1097/01.aids.0000131310.52526.c7 (Pubitemid 38925131)
15. M De La Rosa HW Kim E Gunic C Jenket U Boyle YH Koh I Korboukh M Allan W Zhang H Chen W Xu S Nilar N Yao R Hamatake SA Lang Z Hong Z Zhang JL Girardet 2006 Tri-substituted triazoles as potent non-nucleoside inhibitors of the HIV-1 reverse transcriptase Bioorg Med Chem Lett 16 4444 4449 10.1016/j.bmcl.2006.06. 048 (Pubitemid 44094093)
16. TA Kirschberg M Balakrishnan W Huang R Hluhanich N Kutty AC Liclican DJ McColl NH Squires EB Lansdon 2007 Triazole derivatives as non-nucleoside inhibitors of HIV-1 reverse transcriptase-structure-activity relationships and crystallographic analysis Bioorg Med Chem Lett 18 1131 1134 10.1016/j.bmcl.2007. 11.127 (Pubitemid 351179326)
17. Chemical Computing Group Inc. (2010) MOE. Chemical Computing Group Inc., Montreal (see http://www.chemcomp.com )
18. AN Jain 1996 Scoring noncovalent protein-ligand interactions: a continuous differentiable function tuned to compute binding affinities J Comput Aided-Mol Des 10 427 440 10.1007/BF00124474 1:CAS:528:DyaK28XntV2ms7o%3D (Pubitemid 126712439)
19. RD Cramer III DE Patterson JD Bunce 1989 Recent advances in comparative molecular field analysis (CoMFA) Prog Clin Biol Res 291 161 165 1:CAS:528:DyaL1MXhs1Ggt7Y%3D
20. G Klebe U Abraham T Mietzner 1994 Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity J Med Chem 37 4130 4146 10.1021/jm00050a010 1:CAS:528:DyaK2cXmslWhu7Y%3D (Pubitemid 24379702)
21. Tripos Inc. (2010) Sybyl. Tripos Inc., St. Louis (see tripos.com/sybyl )