Novel modifications in the series of O-(2-phthalimidoethyl)-N-substituted thiocarbamates and their ring-opened congeners as non-nucleoside HIV-1 reverse transcriptase inhibitors

European Journal of Medicinal Chemistry

Volumn 44, Issue 4, 2009, Pages 1650-1663

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

^a UNIVERSITY OF GENOA   (Italy)

^b UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

HIV 1; Molecular docking; Non nucleoside reverse transcriptase inhibitors; O (2 Phthalimidoethyl) N arylthiocarbamates; Parallel synthesis

Indexed keywords

O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 1,1,3,3 TETRAMETHYLBUTYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 2 (3,4 DIMETHOXYPHENYL)ETHYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 2 PHENYLETHYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 2,3 DICHLOROPHENYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 2,3,4 TRICHLOROPHENYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 2,3,5,6 TETRAFLUOROPHENYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 2,4 DICHLOROPHENYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 2,4 DIFLUOROPHENYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 2,4 DIMETHYLPHENYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 2,4,6 TRICHLOROPHENYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 2,4,6 TRIFLUOROPHENYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 2,5 DIFLUOROPHENYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 2,6 DIFLUOROPHENYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 2,6 DIMETHYLPHENYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 3,5 DIFLUOROPHENYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 3,5 DIMETHYLPHENYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL] 4 BROMO 2,6 DIMETHYLPHENYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL]ALLYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL]BENZYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL]BUTYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL]CYCLOHEXYLMETHYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL]CYCLOOCTYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL]CYCLOPENTYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL]CYCLOPROPYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL]FURYLMETHYLTHIOCARBAMATE; O [2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)PROPYL] 4 CHLOROPHENYLTHIOCARBAMATE; RNA DIRECTED DNA POLYMERASE INHIBITOR; THIOCARBAMIC ACID DERIVATIVE; TROVIRDINE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HYBRIDIZATION; MOLECULAR DOCKING; MUTANT; RING OPENING; SIMULATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; WILD TYPE;

DRUG DESIGN; DRUG RESISTANCE, VIRAL; HIV REVERSE TRANSCRIPTASE; HIV-1; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; NUCLEOSIDES; REVERSE TRANSCRIPTASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; THIOCARBAMATES;

EID: 61349101408     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.09.024     Document Type: Article

References (48)

1. Castro H.C., Loureiro N.I., Pujol-Luz M., Souza A.M., Albuquerque M.G., Santos D.O., Cabral L.M., Frugulhetti I.C., and Rodrigues C.R. Curr. Med. Chem. 13 (2006) 313-324 and references therein
2. Kohlstaedt L.A., Wang J., Friedman J.M., Rice P.A., and Steitz T.A. Science 256 (1992) 1783-1790
3. 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) 5633-5639
4. Ren J., Nichols C., Bird L.E., Fujiwara T., Sugimoto H., Stuart D.I., and Stammers D.K. J. Biol. Chem. 275 (2000) 14316-14320
5. Lindberg J., Sigurdsson S., Lowgren S., Andersson H.O., Sahlberg C., Noreen R., Fridborg K., Zhang H., and Unge T. Eur. J. Biochem. 269 (2002) 1670-1677
6. Esnouf R., Ren J., Ross C., Jones Y., Stammers D., and Stuart D. Nat. Struct. Biol. 2 (1995) 303-308
7. Esnouf R.M., Ren J., Hopkins A.L., Ross C.K., Jones E.Y., Stammers D.K., and Stuart D.I. Proc. Natl. Acad. Sci. U.S.A. 94 (1997) 3984-3989
8. Das K., Clark A.D.J., Lewi P.J., Heeres J., De Jonge M.R., Koymans L.M., Vinkers H.M., Daeyaert F., Ludovici D.W., Kukla M.J., De Corte B., Kavash R.W., Ho C.Y., Ye H., Lichtenstein M.A., Andries K., Pauwels R., De Béthune M.P., Boyer P.L., Clark P., Hughes S.H., Janssen P.A., and Arnold E. J. Med. Chem. 47 (2004) 2550-2560
9. Spallarossa A., Cesarini S., Ranise A., Ponassi M., Unge U., and Bolognesi M. Biochem. Biophys. Res. Commun. 365 (2008) 764-770
10. Shaw-Reid C.A., Feuston B., Munshi V., Getty K., Krueger J., Hazuda D.J., Parniak M.A., Miller M.D., and Lewis D. Biochemistry 44 (2005) 1595-1606
11. Sluis-Cremer N., Temiz N.A., and Bahar I. Curr. HIV Res. 2 (2004) 323-332
12. 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
13. 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
14. Ahgren C., 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
15. 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
16. Vig R., Mao C., Venkatachalam T.K., Tuel-Ahlgren L., Sudbeck E.A., and Uckun F.M. Bioorg. Med. Chem. 6 (1998) 1789-1797
17. Mao C., Vig R., Venkatachalam T.K., Sudbeck E.A., and Uckun F.M. Bioorg. Med. Chem. Lett. 8 (1998) 2213-2218
18. Mao C., Sudbeck E.A., Venkatachalam T.K., and Uckun F.M. Bioorg. Med. Chem. Lett. 9 (1999) 1593-1598
19. Sahlberg C., Noréen R., Engelhardt P., Högberg M., Kangasmetsä J., Vrang L., and Zhang H. Bioorg. Med. Chem. Lett. 8 (1998) 1511-1516
20. Uckun F.M., Mao C., Pendergrass S., Maher D., Zhu D., Tuel-Ahlgren L., and Venkatachalam T.K. Bioorg. Med. Chem. Lett. 9 (1999) 2721-2726
21. Uckun F.M., Pendergrass S., Maher D., Zhu D., Tuel-Ahlgren L., Mao C., and Venkatachalam T.K. Bioorg. Med. Chem. Lett. 9 (1999) 3411-3416
22. Uckun F.M., Erbeck D., Tibbles H., Qazi S., and Venkatachalam T.K. Arzneimittelforschung 57 (2007) 164-170
23. 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
24. Högberg M., Engelhardt P., Vrang L., and Zhang H. Bioorg. Med. Chem. Lett. 10 (2000) 265-268
25. 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
26. Campiani G., Fabbrini M., Morelli E., Nacci V., Greco G., Novellino E., Maga G., Spadari S., Bergamini A., Faggioli E., Uccella I., Bolacchi F., Marini S., Coletta M., Fracasso C., and Caccia S. Antiviral Chem. Chemother. 11 (2000) 141-155
27. Venkatachalam T.K., Sudbeck E.A., Mao C., and Uckun F.M. Bioorg. Med. Chem. Lett. 10 (2000) 2071-2074
28. Venkatachalam T.K., Mao C., and Uckun F.M. Bioorg. Med. Chem. 12 (2004) 4275-4284
29. D'Cruz O.J., and Uckun F.M. Curr. HIV Res. 4 (2006) 329-345
30. D'Cruz O.J., and Uckun F.M. J. Antimicrob. Chemother. 57 (2006) 411-423 and references therein
31. D'Cruz O.J., and Uckun F.M. J. Enzyme Inhib. Med. Chem. 21 (2006) 329-350
32. Ravichandran V., and Agrawal R.K. Bioorg. Med. Chem. Lett. 17 (2007) 2197-2202
33. 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
34. 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
35. Rao A., Carbone A., Chimirri A., De Clercq E., Monforte A.M., Monforte P., Pannecouque C., and Zappala M. Il Farmaco 57 (2002) 747-751
36. Rao A., Balzarini J., Carbone A., Chimirri A., De Clercq E., Monforte A.M., Monforte P., Pannecouque C., and Zappala M. Il Farmaco 59 (2004) 33-39
37. La Regina G., Coluccia A., Piscitelli F., Bergamini A., Sinistro A., Cavazza A., Maga G., Samuele A., Zanoli S., Novellino E., Artico M., and Silvestri R. J. Med. Chem. 50 (2007) 5034-5038
38. Maass G., Immendoerfer U., Koenig B., Leser U., Mueller B., Goody R., and Pfaff E. Antimicrob. Agents Chemother. 37 (1993) 2612-2617
39. 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
40. 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
41. Ren J., Esnouf R.M., Hopkins A.L., Warren J., Balzarini J., Stuart D.I., and Stammers D.K. Biochemistry 37 (1998) 14394-14403
42. Carocci A., Catalano A., Corbo F., Duranti A., Amoroso R., Franchini C., Lentini G., and Tortorella V. Tetrahedron: Asymmetry 11 (2000) 3619-3634
43. 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
44. Dauber-Osguthorpe P., Roberts V.A., Osguthorpe D.J., Wolff J., Genest M., and Hagler A.T. Proteins 4 (1988) 31-47
45. 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
46. Collaborative Computational Project, Number 4. Acta Crystallogr. D50 (1994) 760-763
47. Kraulis P.J. J. Appl. Crystallogr. 24 (1991) 946-950
48. Esnouf R.M. J. Mol. Graph. Model. 15 (1997) 132-134