Computational studies of the binding mode and 3D-QSAR analyses of symmetric formimidoester disulfides: A new class of non-nucleoside HIV-1 reverse transcriptase inhibitor

Journal of Molecular Modeling

Volumn 15, Issue 4, 2009, Pages 357-367

  Cichero, Elena ^a   Cesarini, Sara ^a   Spallarossa, Andrea ^a   Mosti, Luisa ^a   Fossa, Paola ^a  

^a UNIVERSITY OF GENOA   (Italy)

Author keywords

3D QSAR; CoMFA; CoMSIA; Disulfides; Docking; HIV 1; Non nucleoside reverse transcriptase inhibitors

Indexed keywords

FORMIMIDOESTER DISULFIDE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CONTROLLED STUDY; DRUG BINDING; DRUG STRUCTURE; GEOMETRY; ISOMER; MOLECULAR DOCKING; PARTIAL LEAST SQUARES REGRESSION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

COMPUTER SIMULATION; DISULFIDES; DRUG EVALUATION, PRECLINICAL; FORMIC ACID ESTERS; HIV INFECTIONS; HIV REVERSE TRANSCRIPTASE; MODELS, MOLECULAR; REVERSE TRANSCRIPTASE INHIBITORS;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 60849104780     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-008-0402-0     Document Type: Article

References (26)

1. Jonckheere H, Anne J, De Clercq E (2000) The HIV-1 reverse transcription (RT) process as target for RT inhibitors. Med Res Rev 20:129-154. doi: 10.1002/(SICI)1098-1128(200003)20:2<129::AID-MED2>3.0.CO;2-A
2. De Clercq E (2001) New developments in anti-HIV chemotherapy. Farmaco 56:3-12. doi: 10.1016/S0014-827X(01)01007-2
3. De Clercq E (2005) Emerging anti-HIV drugs. Expert Opin Emerg Drugs 10:241-273. doi: 10.1517/14728214.10.2.241
4. De Clercq E (2005) New approaches toward anti-HIV chemotherapy. J Med Chem 48:1297-1313. doi: 10.1021/jm040158k
5. Barbaro G, Scozzafava A, Mastrolorenzo A, Supuran CT (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. doi: 10.2174/1381612053764869
6. Balzarini J (2004) Current status of the non-nucleoside reverse transcriptase inhibitors of human immunodeficiency virus type 1. Curr Top Med Chem 4:921-944. doi: 10.2174/1568026043388420
7. De Clercq E (1998) The role of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection. Antivir Res 38:153-179. doi: 10.1016/S0166-3542(98)00025-4
8. Pedersen OS, Pedersen EB (1999) Non-nucleoside reverse transcriptase inhibitors, the NNRTI boom. Antivir Chem Chemother 10:285-314
9. Pedersen OS, Pedersen EB (2000) The flourishing syntheses of non-nucleoside reverse transcriptase inhibitors. Synthesis 4:479-495. doi: 10.1055/s-2000-6357
10. Campiani G, Ramunno A, Maga G, Nacci V, Fattorusso C, Catalanotti B et al (2002) Non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors: past, present, and future perspectives. Curr Pharm Des 8:615-657. doi: 10.2174/1381612024607207
11. De Clercq E (2004) Non-nucleoside reverse transcriptase inhibitors (NNRTIs): Past, present, and future. Chem Biodivers 1:44-64. doi: 10.1002/cbdv.200490012
12. Pauwels R (2004) New non-nucleoside reverse transcriptase inhibitors (NNRTIs) in development for the treatment of HIV infections. Curr Opin Pharmacol 4:437-446. doi: 10.1016/j.coph.2004.07.005
13. Leigh Brown AJ, Frost SD, Mathews WC, Dawson K, Hellmann NS, Daar ES et al (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. doi: 10.1086/367989
14. Richman DD, Morton SC, Wrin T, Hellmann N, Berry S, Shapiro MF et al (2004) The prevalence of antiretroviral drug resistance in the United States. AIDS 18:1393-1401. doi: 10.1097/01.aids.0000131310.52526.c7
15. Spallarossa A; Cesarini S; Ranise A; Bruno O; Schenone S; La Colla P; Collu G; Sanna G; Secci B; Loddo R (2008)Novel modifications in the series of O-(2-phenylethyl)-N-substituted thiocarbamates and their ring-opened congeners as non-nucleoside HIV-1 reverse transcriptase inhibitors. Eur J Med Chem (in press). doi: 10.1016/j.ejmech.2008.09.024
16. Ranise A, Spallarossa A, Cesarini S, Bondavalli F, Schenone S, Bruno O et al (2005) Structure-based design, parallel synthesis, structure-activity relationship, and molecular modeling studies of thiocarbamates, new potent non-nucleoside HIV-1 reverse transcriptase inhibitor isosteres of phenethylthiazolylthiourea derivatives. J Med Chem 48:3858-3873. doi: 10.1021/jm049252r
17. Spallarossa A, Cesarini S, Ranise A, Schenone S, Bruno O, Borassi A, La Colla P, Pezzullo M, Sanna G, Collu G, Secci B, Loddo R (2008) Parallel synthesis, molecular modelling and further structure-activity relationship studies of new acylthiocarbamates as potent non-nucleoside HIV-1 reverse transcriptase inhibitors. Eur J Med Chem (in press). doi: 10.1016/j.ejmech.2008.10.032
18. Ranise A, Spallarossa A, Schenone S, Bruno O, Bondavalli F, Vargiu L, Marceddu T, Mura M, La Colla P, Pani A (2003) Design, synthesis, SAR, and molecular modeling studies of acylthiocarbamates: A novel series of potent non-nucleoside HIV-1 reverse transcriptase inhibitors structurally related to phenethylthiazolylthiourea derivatives. J Med Chem 46:768-781. doi: 10.1021/jm0209984
19. Cesarini S, Spallarossa A, Ranise A, Bruno O, La Colla P, Secci B et al (2008) Thiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 2: Parallel synthesis, molecular modelling and structure-activity relationship studies on analogues of O-(2-phenylethyl)-N-phenylthiocarbamate. Bioorg Med Chem 16:4173-4185. doi: 10.1016/j.bmc.2007.12.046
20. Cesarini S, Spallarossa A, Ranise A, Fossa P, La Colla P, Sanna G et al (2008) Thiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 1: Parallel synthesis, molecular modelling and structure-activity relationship studies on O-[2-(hetero)arylethyl]-N-phenylthiocarbamates. Bioorg Med Chem 16:4160-4172. doi: 10.1016/j.bmc.2007.12.050
21. Cesarini S, Spallarossa A, Ranise A, Schenone S, Bruno O, La Colla P et al (2008) Parallel one-pot synthesis and structure-activity relationship study of symmetric formimidoester disulfides as a novel class of potent non-nucleoside HIV-1 reverse transcriptase inhibitors. Bioorg Med Chem 16:6353-6363. doi: 10.1016/j.bmc.2008.05.010
22. Spallarossa A, Cesarini S, Ranise A, Ponassi M, Unge T, Bolognesi M (2008) Crystal structures of HIV-1 reverse transcriptase complexes with thiocarbamate non-nucleoside inhibitors. Biochem Biophys Res Commun 365:764-770. doi: 10.1016/j.bbrc.2007.11.036
23. MOE Chemical Computing Group Inc. Montreal. H3A 2R7 Canada. http://www.chemcomp.com
24. Cramer RD III, Patterson DE, Bunce JD (1989) Recent advances in comparative molecular field analysis. CoMFA. Prog Clin Biol Res 291:1-165
25. Klebe G, Abraham U, Mietzner T (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. doi: 10.1021/ jm00050a010
26. Sybyl7.0, Tripos Inc 1699 South Hanley Road, St Louis, Mo, USA