Anti-HIV agents: Design and discovery of new potent RT inhibitors

Farmaco

Volumn 58, Issue 3, 2003, Pages 259-263

  Barreca, Maria Letizia ^a   Chimirri, Alba ^a   De Clercq, Erik ^b   De Luca, Laura ^a   Monforte, Anna Maria ^a   Monforte, Pietro ^a   Rao, Angela ^a   Zappalà, Maria ^a  

^a UNIVERSITY OF MESSINA   (Italy)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

2,3 Diaryl 1,3 thiazolidin 4 ones; Anti HIV agents; NNRTIs

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; BENZIMIDAZOLE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR; THIAZOLIDINE DERIVATIVE;

ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG EFFECT; DRUG IDENTIFICATION; DRUG POTENCY; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; MOLECULAR MODEL; NONHUMAN; STRUCTURE ACTIVITY RELATION; VIRUS REPLICATION; VIRUS STRAIN;

EID: 0037374246     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(03)00024-7     Document Type: Article

References (20)

1. Jonckheere H., Anné J., De Clercq E. The HIV-1 reverse transciption (RT) process as target for RT inhibitors. Med. Res. Rev. 20:2000;129-154.
2. De Clercq E. Novel compounds in preclinical/early clinical development for the treatment of HIV infections. Rev. Med. Virol. 10:2000;255-277.
3. Hajos G., Riedi S., Molnar J., Szabo D. Nonnucleoside reverse transcriptase inhibitors. Drugs Future. 25:2000;47-62.
4. Ren J., Milton J., Weaver K.L., Short S.A., Stuart D.I., Stammers D.K. Structural basis for the resilience of Efavirenz (DMP-266) to drug resistance mutations in HIV-1 reverse transcriptase. Strucure. 8:2000;1089-1094.
5. Pedersen O.S., Pedersen O.B. Non-nucleoside reverse transcriptase inhibitors: the NNRTI boom. Antiv. Chem. Chemother. 10:1999;285-314.
6. Chimirri A., Grasso S., Monforte A.M., Monforte P., Zappalà M. Anti-HIV agents II. Synthesis and in vitro anti-HIV activity of novel 1H,3H-thiazolo[3,4-a]benzimidazoles. Farmaco. 46:1991;925-933.
7. P. Monforte, A.M Monforte, M. Zappalà, G. Romeo, S. Grasso, A. Chimirri, 1-Phenyl substituted 1H,3H-thiazolo[3,4-a]benzimidazoles and pharmaceutical compositions containing them, US Patent, 5 (1993) 217,984.
8. Chimirri A., Grasso S., Molica C., Monforte A.M., Monforte P., Zappalà M., Bruno G., Nicolò F., Witvrouw M., Jonckeere H., Balzarini J., De Clercq E. Structural features and anti-human immunodeficiency virus (HIV) activity of the isomers of 1-(2′,6′-difluorophenyl)-1H,3H-thiazolo[3,4-a]benzimidazole, a potent non-nucleoside HIV-1 reverse transcriptase inhibitor. Antivir. Chem. Chemother. 8:1997;363-370.
9. Chimirri A., Grasso S., Monforte A.M., Monforte P., Rao A., Zappalà M., Bruno G., Nicolò F., Scopelliti R. Anti-HIV agents. V. Synthesis, structure and in vitro anti-HIV activity of novel 1H,3H-naphtho[2′,3′:4,5]imidazo[1,2-c]thiazoles. Farmaco. 52:1997;673-677.
10. Chimirri A., Grasso S., Monforte P., Rao A., Zappalà M., Monforte A.M., Pannecouque C., Witvrouw M., Balzarini J., De Clercq E. Synthesis and biological activity of novel 1h,3h-thiazolo[3,4-a]benzimidazoles: non-nucleoside human immunodeficiency virus type 1 reverse transcriptase inhibitors. Antivir. Chem. Chemother. 10:1999;211-217.
11. Chimirri A., Grasso S., Monforte A.M., Monforte P., Rao A., Zappalà M., Bruno G., Nicolò F., Pannecouque C., Witvrouw M., De Clercq E. Synthesis, structure and in vitro anti-human immunodeficiency virus activity of novel 3-methyl-1H,3H-thiazolo[3,4-a]benzimidazoles. Antivir. Chem. Chemother. 9:1998;431-438.
12. Chimirri A., Monforte A.M., Monforte P., Nicolò F., Rao A., Zappalà M. Synthesis and structural features of new cyclofunctionalized benzimidazoles. Heterocycles. 3:2000;613-620.
13. Roth T., Morningstar M.L., Boyer P.L., Hughes S.H., Buckheit R.W., Michejda C.J. Synthesis and biological activity of novel nonnucleoside inhibitors of HIV-1 reverse transcriptase. 2-Aryl-substituted benzimidazoles. J. Med. Chem. 40:1997;4199-4207.
14. Rao A., Chimirri A., De Clercq E., Monforte A.M., Monforte P., Pannecouque C., Zappalà M. Synthesis and anti-HIV activity of TBZ structurally-related 1,2-substituted benzimidazoles. Il Farmaco. 57:2002;819-823.
15. Chimirri A., Monforte P., Rao A., Zappalà M., Monforte A.M., De Sarro G., Pannecouque C., Witvrouw M., Balzarini J., De Clercq E. Synthesis, biological activity, pharmacokinetic properties and molecular modelling studies of novel 1H,3H-oxazolo[3,4-a]benzimidazoles: non-nucleoside HIV-1 reverse transcriptase inhibitors. Antivir. Chem. Chemother. 12:2001;169-174.
16. Barreca M.L., Chimirri A., Carotti A., Carrieri A., Monforte A.M., Pellegrini Calace M., Rao A. Comparative molecular field analysis (CoMFA) and docking studies of non-nucleoside HIV-1 RT inhibitors (NNRTIs). Bioorg. Med. Chem. 7:1999;2283-2292.
17. Barreca M.L., Chimirri A., De Luca L., Monforte A.M., Monforte P., Rao A., Zappalà M., Balzarini J., De Clercq E., Pannecouque C., Witvrouw M. Discovery of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti-HIV-1 agents. Bioorg. Med. Chem. Lett. 11:2001;1793-1796.
18. Goodford P.J. A computational procedure for determining energetically favorable binding sites on biologically important macromolecules. J. Med. Chem. 28:1985;849-857.
19. M.L. Barreca, A. Chimirri, E. De Clercq, L. De Luca, H.D. Höltje, M. Höltje, A.M. Monforte, P. Monforte, A. Rao, M. Zappalà, Discovery of 2,3-diaryl-1,3-thiazolidin-4-ones as potent HIV-1 NNRTIs by molecular modeling studies, First Magna Graecia Medicinal Chemistry Workshop on New Perspectives in Medicinal Chemistry, Copanello (CZ), 2001, p. 87.
20. M.L. Barreca, L. De Luca, A.M. Monforte, P. Monforte, A. Rao, M. Zappalà, A. Chimirri, Computational approaches in discovering novel anti-AIDS agents, Biomolecular Interactions MGMS Annual international Meeting, Bristol, UK, P3, 2002, p. 47.