Novel thiolactone-isatin hybrids as potential antimalarial and antitubercular agents

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 7, 2011, Pages 2055-2058

  Hans, Renate H ^a   Wiid, Ian J F ^b   Van Helden, Paul D ^b   Wan, Baojie ^c   Franzblau, Scott G ^c   Gut, Jiri ^d   Rosenthal, Philip J ^d   Chibale, Kelly ^e  

^a UNIVERSITY OF NAMIBIA   (Namibia)

^b STELLENBOSCH UNIVERSITY   (South Africa)

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

^e UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

Antimalaria; Antitubercular; Hybrids; Isatin; Thiolactone

Indexed keywords

6,7 DIHYDRO 2 NITRO 6 (4 TRIFLUOROMETHOXYBENZYLOXY) 5H IMIDAZO[2,1 B][1,3]OXAZINE; ANTIMALARIAL AGENT; CHLOROQUINE; ISATIN DERIVATIVE; ISONIAZID; MOXIFLOXACIN; RECOMBINANT PROTEIN; RIFAMPICIN; STREPTOMYCIN; THIOLACTOMYCIN; THIOLACTONE; TUBERCULOSTATIC AGENT;

ANTIMALARIAL ACTIVITY; ANTITUBERCULAR ACTIVITY; ARTICLE; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; GROWTH INHIBITION; IC 50; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIMALARIALS; ANTITUBERCULAR AGENTS; ISATIN; LACTONES; MYCOBACTERIUM TUBERCULOSIS; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP;

MYCOBACTERIUM TUBERCULOSIS; PLASMODIUM FALCIPARUM;

EID: 79952490806     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.02.008     Document Type: Article

References (41)

1. (a) Biot, C.; Chibale, K. Infect. Disord.: Drug Targets 2006, 6, 173;
2. (b) Tietze, L. F.; Bell, H. P.; Chandrasekhar, S. Angew. Chem., Int. Ed. 2003, 42, 3996.
3. (a) Chiyanzu, I.; Clarkson, C.; Smith, P. J.; Lehman, J.; Gut, J.; Rosenthal, P. J.; Chibale, K. Bioorg. Med. Chem. 2005, 13, 3249;
4. (b) Chiyanzu, I.; Hansell, E.; Gut, J.; Rosenthal, P. J.; McKerrow, J. H.; Chibale, K. Bioorg. Med. Chem. Lett. 2003, 13, 3527.
5. (a) Oishi, H.; Noto, T.; Sasaki, H.; Suzuki, K.; Hayashi, T.; Okazaki, H.; Ando, K.; Sawada, M. J. Antibiot. (Tokyo) 1982, 35, 391;
6. (b) Noto, T.; Miyakawa, S.; Oishi, H.; Endo, H.; Okazaki, H. J. Antibiot. (Tokyo) 1982, 35, 401.
7. Kremer, L.; Douglas, J. D.; Baulard, A. R.; Morehouse, C.; Guy, M. R.; Alland, D.; Dover, L. G.; Lakey, J. H.; Jacobs, W. R., Jr.; Brennan, P. J.; Minnikin, D. E.; Besra, G. S. J. Biol. Chem. 2000, 275, 16857.
8. Waller, R. F.; Keeling, P. J.; Donald, R. G. K.; Striepen, B.; Handman, E.; Lang-Unnasch, N.; Cowman, A. F.; Besra, G. S.; Roos, D. S.; McFadden, G. I. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12352.
9. Jones, S. M.; Urch, J. E.; Brun, R.; Harwood, J. L.; Berry, C.; Gilbert, I. H. Bioorg. Med. Chem. 2004, 12, 683.
10. Morita, Y. S.; Paul, K. S.; Englund, P. T. Science 2000, 288, 140.
11. (a) Kim, P.; Zhang, Y.-M.; Shenoy, G.; Nguyen, Q.-A.; Boshoff, H. I.; Manjunatha, U. H.; Goodwin, M. B.; Lonsdale, J.; Price, A. C.; Miller, D. J.; White, S. W.; Rock, C. O.; Barry, C. E., III; Dowd, C. S. J. Med. Chem. 2006, 49, 159;
12. (b) McFadden, J. M.; Medghalchi, S. M.; Thupari, J. N.; Pinn, M. L.; Vadlamudi, A.; Miller, K. I.; Kuhajda, F. P.; Townsend, C. A. J. Med. Chem. 2005, 48, 946;
13. (c) Jones, S. M.; Urch, J. E.; Kaiser, M.; Brun, R.; Harwood, J. L.; Berry, C.; Gilbert, I. H. J. Med. Chem. 2005, 48, 5932;
14. (d) Kamal, A.; Shaik, A. A.; Sinha, R.; Yadav, J. S.; Arora, S. K. Bioorg. Med. Chem. Lett. 2005, 15, 1927.
15. (a) Krishnan, S. S.; Pandeya, N. S.; Stables, J. P.; Ramesh, A. Eur. J. Pharm. Sci. 2002, 16, 129;
16. (b) Daisley, R. W.; Shah, V. K. J. Pharm. Sci. 1984, 73, 407;
17. (c) Varma, R. S.; Nobles, W. L. J. Med. Chem. 1967, 10, 972;
18. (d) Sridhar, S. K.; Ramesh, A., Biol. Pharm. Bull. 2001, 24, 1149;
19. (e) Piscopo, E.; Diurno, M. V.; Gogliardi, R.; Cucciniello, M.; Veneruso, G. Boll. Soc. Ital. Biol. Sper. 1981, 63, 827;
20. (f) Varma, R. S.; Khan, C. A. Pol. J. Pharmacol. Pharm. 1977, 29, 549;
21. (g) Sarciron, S. E.; Audin, P.; Delebre, I.; Gabrion, C.; Petavy, A. F.; Paris, J. J. Pharm. Sci. 1993, 82, 605;
22. (h) Pandeya, S. N.; Sriram, D.; De Clerq, E.; Panne-Couque, C.; Witurouw, M. Indian J. Pharm. Sci. 1998, 60, 207;
23. (i) Karali, N.; Terzioǧlu, N.; Gürsoy, A. Arzneimittelforschung 1998, 48, 758;
24. (j) Sriram, D.; Yogeeswari, P.; Gopal, G. Eur. J. Med. Chem. 2005, 40, 1373;
25. (k) Karali, N.; Gürsoy, A.; Kandemirli, F.; Shvets, N.; Kaynak, F. B.; Özbey, S.; Kovalishyn, V.; Dimoglo, A. Bioorg. Med. Chem. 2007, 15, 5888;
26. (l) Karali, N. Eur. J. Med. Chem. 2002, 37, 909;
27. (m) Terzioglu, N.; Karali, N.; Gürsoy, A.; Pannecouque, C.; Leysen, P.; Paeshuyse, J.; Neyts, J.; De Clercq, E. ARKIVOC 2006, i, 109;
28. (n) Webber, S. E.; Tikhe, J.; Worland, S. T.; Fuhrman, S. A.; Hendrickson, T. F.; Matthews, D. A.; Love, R. A.; Patick, A. K.; Meador, J. W.; Ferre, R. A.; Brown, E. L.; DeLisle, D. M.; Ford, C. E.; Binford, S. L. J. Med. Chem. 1996, 39, 5072;
29. (o) Lyer, R. A.; Hanna, P. E. Bioorg. Med. Chem. Lett. 1995, 5, 89.
30. Hans, R. H.; Su, H.; Chibale, K. Beilstein J. Org. Chem. 2010, 78. doi:10.3762/bjoc.6.78.
31. Wang, C.-L. J.; Salvino, J. M. Tetrahedron Lett. 1984, 25, 5246.
32. Chu, W.; Rothfuss, J.; Chu, Y.; Zhou, D.; Mach, R. H. J. Med. Chem. 2009, 52, 2188.
33. Greenbaum, D. C.; Mackey, Z.; Hansell, E.; Doyle, P.; Gut, J.; Caffrey, C. R.; Lehman, J.; Rosenthal, P. J.; McKerrow, J. H.; Chibale, K. J. Med. Chem. 2004, 47, 3212.
34. (a) Collins, L. A.; Franzblau, S. G. Antimicrob. Agents Chemother. 1997, 41, 1004;
35. (b) Cho, S. H.; Goodlet, D.; Franzblau, S. G. Tuberculosis (Edinb.) 2006, 86, 445;
36. (c) Pauli, G. F. R.; Case, R. J.; Inui, T.; Wang, Y.; Cho, S.; Fischer, N. H.; Franzblau, S. G. Life Sci. 2005, 78, 485.
37. (a) Warren, R.; Richardson, M.; Sampson, S.; Hauman, J. H.; Beyers, N.; Donald, P. R.; Van Helden, P. D. J. Clin. Microbiol. 1996, 34, 2219;
38. (b) Somoskovi, A.; Magyar, P. J. Clin. Microbiol. 1999, 37, 1366;
39. (c) Siddiqi, S. H. 460TB system. Product and Procedure Manual; Becton Dickinson and Company: Maryland, USA, 1995.
40. (a) Vaughan, A. M.; O'Neill, M. T.; Tarun, A. S.; Camargo, N.; Phuong, T. M.; Aly, A. S. I.; Cowman, A. F.; Kappe, S. H. I. Cell. Microbiol. 2009, 11, 506;
41. (b) Min Yu, M.; Kumar, S. T. R.; Nkrumah, L. J.; Coppi, C.; Retzlaff, S.; Li, C. D.; Kelly, B. J.; Moura, P. A.; Lakshmanan, V.; Freundlich, J. S.; Valderramos, J.-C.; Vilcheze, C.; Siedner, M.; Tsai, J.-H. C.; Falkard, B.; Sidhu, A. B.; Purcell, L. A.; Gratraud, P.; Kremer, L.; Waters, A. P.; Schiehser, G.; Jacobus, D. P.; Janse, C. J.; Ager, A.; Jacobs, W. R., Jr.; Sacchettini, J. C.; Heussler, V.; Sinnis, P.; Fidock, D. A. Cell Host Microbe 2008, 4, 567.