Parallel synthesis, molecular modelling and further structure-activity relationship studies of new acylthiocarbamates as potent non-nucleoside HIV-1 reverse transcriptase inhibitors

European Journal of Medicinal Chemistry

Volumn 44, Issue 5, 2009, Pages 2190-2201

  Spallarossa, Andrea ^a   Cesarini, Sara ^a   Ranise, Angelo ^a   Schenone, Silvia ^a   Bruno, Olga ^a   Borassi, Alberto ^a   La Colla, Paolo ^b   Pezzullo, Margherita ^b   Sanna, Giuseppina ^b   Collu, Gabriella ^b   Secci, Barbara ^b   Loddo, Roberta ^b  

^a UNIVERSITY OF GENOA   (Italy)

^b UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

Acylthiocarbamates; HIV 1; Non nucleoside reverse transcriptase inhibitors; Parallel synthesis

Indexed keywords

ACYLTHIOCARBAMATE; EFAVIRENZ; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 2 METHYLBENZOYL(4 METHYLPHENYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 3 METHYLBENZOYL(4 METHYLPHENYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 3,4 DICHLOROBENZOYL(PHENYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 BROMOBENZOYL(4 BROMOPHENYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 BROMOPHENYL[(2 CHLOROPYRIDIN 3 YL)CARBONYL]THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 CHLORO 3 NITROBENZOYL(PHENYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 CHLOROPHENYL(2 METHYLBENZOYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 CHLOROPHENYL(2 NITROBENZOYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 CHLOROPHENYL(2,3 DIFLUOROBENZOYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 CHLOROPHENYL(2,4 DIFLUOROBENZOYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 CHLOROPHENYL(2,5 DIFLUOROBENZOYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 CHLOROPHENYL(3 METHYLBENZOYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 CHLOROPHENYL(3 NITROBENZOYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 CHLOROPHENYL(3,4 DIFLUOROBENZOYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 CHLOROPHENYL(4 METHYLBENZOYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 CHLOROPHENYL(4 NITROBENZOYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 CHLOROPHENYL(4 TRIFLUOROMETYLBENZOYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 FLUOROPHENYL[4 (PENTYLOXY)BENZOYL]THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 METHYLBENZOYL(4 METHYLPHENYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 METHYLPHENYL(2 NITROBENZOYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 METHYLPHENYL(3 NITROBENZOYL)THIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 METHYLPHENYL(4 NITROBENZOYL)THIOCARBAMATE; O [2 PHTHALIMIDOETHYL] 4 CHLOROPHENYL(3 NITROBENZOYL)THIOCARBAMATE; O [2-(1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 CHLOROPHENYL(2,6 DIFLUOROBENZOYL)THIOCARBAMATE; RNA DIRECTED DNA POLYMERASE INHIBITOR; THIOCARBAMIC ACID DERIVATIVE; TROVIRDINE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; MOLECULAR MODEL; STRUCTURE ACTIVITY RELATION; VIRUS MUTATION; VIRUS STRAIN;

COMPUTER SIMULATION; HIV REVERSE TRANSCRIPTASE; HIV-1; MODELS, MOLECULAR; MUTATION, MISSENSE; PROTEIN BINDING; REVERSE TRANSCRIPTASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; THIOCARBAMATES;

EID: 62549143085     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.10.032     Document Type: Article

References (36)

1. Artico M. Farmaco 51 (1996) 305-331
2. Artico M. Drugs Future 27 (2002) 159-175
3. Balzarini J. Curr. Top. Med. Chem. 4 (2004) 921-944
4. De Clercq E. Chem. Biodivers. 1 (2004) 44-64
5. De Clercq E. J. Med. Chem. 46 (2005) 1297-1313
6. Pauwels R. Curr. Opin. Pharmacol. 4 (2004) 437-446
7. Pedersen O.S., and Pedersen E.B. Antivir. Chem. Chemother. 10 (1999) 285-314
8. Pedersen O.S., and Pedersen E.B. Synthesis 4 (2000) 479-495
9. Tucker T.J., Lumma W.C., and Culberson J.C. Methods Enzymol. 275 (1996) 440-472
10. Ranise A., Spallarossa A., Schenone S., Bruno O., Bondavalli F., Vargiu L., Marceddu T., Mura M., La Colla P., and Pani A. J. Med. Chem. 46 (2003) 768-781
11. Ahgren A., Backro K., Bell F.W., Cantrell A.S., Clemens M., Colacino J.M., Deeter J.B., Engelhardt P., Hogberg M., Jaskunas S.R., Johansson N.G., Jordan C.L., Kasher J.S., Kinnick M.D., Lind P., Lopez C., Morin Jr. J.M., Muesing M.A., Noreen R., Oberg B., Paget C.J., Palkowitz J.A., Parrish C.A., Pranc P., Rippy M.K., Rydergard C., Sahlberg C., Swanson S., Ternansky R.J., Unge T., Vasileff R.T., Vrang L., West S.J., Zhang H., and Zhou X.-X. Antimicrob. Agents Chemother. 39 (1995) 1329-1335
12. Cantrell A.S., Engelhardt P., Hogberg M., Jaskunas S.R., Johansson N.G., Jordan C.L., Kangasmetsa J., Kinnick M.D., Lind P., Morin Jr. J.M., Muesing M.A., Noreen R., Oberg B., Pranc P., Sahlberg C., Ternansky R.J., Vasileff R.T., Vrang L., West S.J., and Zhang H. J. Med. Chem. 39 (1996) 4261-4274
13. D'Cruz O.J., and Uckun F.M. J. Antimicrob. Chemother. 57 (2006) 411-423 and references therein
14. Dong Y., Venkatachalam T.K., Narla R.K., Trieu V.N., Sudbeck E.A., and Uckun F.M. Bioorg. Med. Chem. Lett. 10 (2000) 87-90 and references therein
15. Högberg M., Sahlberg C., Engelhardt P., Noréen R., Kangasmetsä J., Johansson N.G., Öberg B., Vrang L., Zhang H., Sahlberg B.-L., Unge T., Lövgren S., Fridborg K., and Bäckbro K. J. Med. Chem. 42 (1999) 4150-4160
16. Ravichandran V., and Agrawal R.K. Bioorg. Med. Chem. Lett. 17 (2007) 2197-2202
17. Uckun F.M., Erbeck D., Tibbles H., Qazi S., and Venkatachalam T.K. Arzneimittelforschung 57 (2007) 164-170
18. Venkatachalam T.K., Sudbeck E.A., Mao C., and Uckun F.M. Bioorg. Med. Chem. Lett. 10 (2000) 2071-2074
19. Venkatachalam T.K., Mao C., and Uckun F.M. Bioorg. Med. Chem. 12 (2004) 4275-4284
20. Ranise A., Spallarossa A., Cesarini S., Bondavalli F., Schenone S., Bruno O., Menozzi G., Fossa P., Mosti L., La Colla M., Sanna G., Murreddu M., Collu G., Busonera B., Matongiu M.E., Pani A., La Colla P., and Loddo R. J. Med. Chem. 48 (2005) 3858-3873
21. Cesarini S., Spallarossa A., Ranise A., Fossa P., La Colla P., Sanna G., Collu G., and Loddo R. Bioorg. Med. Chem. 16 (2008) 4160-4172
22. Cesarini S., Spallarossa A., Ranise A., Bruno O., La Colla P., Secci B., Collu G., and Loddo R. Bioorg. Med. Chem. 16 (2008) 4173-4185
23. Spallarossa A., Cesarini S., Ranise A., Bruno O., Schenone S., La Colla P., Collu G., Sanna G., Secci B., and Loddo R. Eur. J. Med. Chem. (2008) 10.1016/j.ejmech.2008.09.024
24. Tantillo C., Ding J., Jacobo-Molina A., Nanni R.G., Boyer P.L., Hughes S.H., Pauwels R., Andries K., Janssen P.A., and Arnold E. J. Mol. Biol. 243 (1994) 369-387
25. Maass G., Immendoerfer U., Koenig B., Leser U., Mueller B., Goody R., and Pfaff E. Antimicrob. Agents Chemother. 37 (1993) 2612-2617
26. Motakis D., and Parniak M.A. Antimicrob. Agents Chemother. 46 (2002) 1851-1856
27. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. J. Comput. Chem. 19 (1998) 1639-1662
28. Ren J., Diprose J., Warren J., Esnouf R.M., Bird L.E., Ikemizu S., Slater M., Milton J., Balzarini J., Stuart D.I., and Stammers D.K. J. Biol. Chem. 275 (2000) 5633
29. Auffinger P., Hays F.A., Westhof E., and Ho P.S. Proc. Natl. Acad. Sci. U S A 101 (2004) 16789-16794
30. Mugnoli A., Borassi A., Spallarossa A., and Cesarini S. Acta Crystallogr. C62 (2006) 315-317
31. Bell F.W., Cantrell A.S., Hogberg M., Jaskunas S.R., Johansson N.G., Jordan C.L., Kinnick M.D., Lind P., Morin Jr. J.M., Noreen R., Oberg B., Palkowitz J.A., Parrish C.A., Pranc P., Sahlberg C., Ternansky R.J., Vasileff R.T., Vrang L., West S.J., Zhang H., and Zhou X.-X. J. Med. Chem. 38 (1995) 4929-4936
32. Dauber-Osguthorpe P., Roberts V.A., Osguthorpe D.J., Wolff J., Genest M., and Hagler A.T. Proteins 4 (1988) 31-47
33. Brunger A.T., Adams P.D., Clore G.M., Delano W.L., Gros P., Grosse-Kunstleve R.W., Jiangj S., Kuszewski J., Nilges N., Pannu N.S., Read R.J., Rice L.M., Simonson T., and Warren G.L. Acta Crystallogr. D54 (1998) 905-921
34. Collaborative Computational Project, Number 4. Acta Crystallogr. D50 (1994) 760-763
35. Kraulis P.J. J. Appl. Crystallogr. 24 (1991) 946-950
36. Esnouf R.M. J. Mol. Graph. Model. 15 (1997) 132-134