Sulfur rich 2-mercaptobenzothiazole and 1,2,3-triazole conjugates as novel antitubercular agents

European Journal of Medicinal Chemistry

Volumn 76, Issue , 2014, Pages 274-283

  Mir, Fauzia ^a   Shafi, Syed ^a   Zaman, M S ^b   Kalia, Nitin Pal ^c   Rajput, Vikrant S ^c   Mulakayala, Chaitanya ^d   Mulakayala, Naveen ^e   Khan, Inshad A ^c   Alam, M S ^a  

^a HAMDARD UNIVERSITY   (India)

^b HAMDARD UNIVERSITY   (India)

^c Dept of Pharmaceutical Technology   (India)

^d SRI SATHYA SAI INSTITUTE OF HIGHER LEARNING   (India)

^e INSTITUTE OF LIFE SCIENCES   (India)

Author keywords

1,2,3 Triazole; Antitubercular activity; Bactericidal; Benzothiazole; H37Rv; Indole 3 glyoxalic acid

Indexed keywords

1 (1H INDOL 3 YL) 2 (4 METHYLPIPERAZIN 1 YL)ETHANE 1,2 DIONE; 1 (1H INDOL 3 YL) 2 (PIPERIDIN 1 YL)ETHANE 1,2 DIONE; 1 (1H INDOL 3 YL) 2 (PYRROLIDIN 1 YL)ETHANE 1,2 DIONE; 1 (1H INDOL 3 YL) 2 MORPHOLINOETHANE 1,2 DIONE; 1 (1H INDOL 3 YL) 2 THIOMORPHOLINOETHANE 1,2 DIONE; 1,2,3 TRIAZOLE DERIVATIVE; 2 (1H INDOL 3 YL) N MORPHOLINO 2 OXOACETAMIDE; 2 (BENZO[D]THIAZOL 2 YLTHIO) 1 (4 METHYLPIPERAZIN 1 YL)ETHANONE; 2 (BENZO[D]THIAZOL 2 YLTHIO) 1 (PIPERIDIN 1 YL)ETHANONE; 2 (BENZO[D]THIAZOL 2 YLTHIO) 1 (PYRROLIDIN 1 YL)EHTANONE; 2 (BENZO[D]THIAZOL 2 YLTHIO) 1 MORPHOLINOETHANONE; 2 (BENZO[D]THIAZOL 2 YLTHIO) 1 THIOMORPHOLINOETHANONE; 2 (BENZO[D]THIAZOL 2 YLTHIO) N (4 BROMOPHENYL)ACETAMIDE; 2 (BENZO[D]THIAZOL 2 YLTHIO) N (4 FLUOROPHENYL)ACETAMIDE; 2 (BENZO[D]THIAZOL 2 YLTHIO) N (PYRIDIN 2 YL)ACETAMIDE; 2 (BENZO[D]THIAZOL 2 YLTHIO) N MORPHOLINOACETAMIDE; 2 (BENZO[D]THIAZOL 2 YLTHIO) N' (PYRIDIN 4 YL)ACETOHYDRAZIDE; 2 MERCAPTOBENZOTHIAZOLE; INDOLE DERIVATIVE; ISONIAZID; N (4 FLUOROBENZYL) 2 (BENZO[D]THIAZOL 2 YLTHIO)ACETAMIDE; N' [2 (1H INDOL 3 YL) 2 OXOACETYL]PYRIDINE 4 CARBOHYDRAZIDE; RIFAMPICIN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; BENZOTHIAZOLE DERIVATIVE; SULFUR;

ARTICLE; BACTERIAL GROWTH; BACTERIAL STRAIN; BROTH DILUTION; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG CONJUGATION; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTEIN STRUCTURE; CHEMISTRY; DRUG EFFECTS; ELECTROSPRAY MASS SPECTROMETRY; MICROBIAL SENSITIVITY TEST; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ANTITUBERCULAR AGENTS; BENZOTHIAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MOLECULAR DOCKING SIMULATION; MYCOBACTERIUM TUBERCULOSIS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFUR;

EID: 84896808581     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.02.017     Document Type: Article

References (44)

1. L.V. Sacks, and R.E. Behrman Future Medicinal Chemistry 1 2009 749 756
2. K. Duncan Tuberculosis 83 2003 201 207
3. C.E. Barry III, and K. Duncan Drug Discovery Today - Therapeutic Strategies 1 2004 491 496
4. N. Boechat, V.F. Ferreira, S.B. Ferreira, M.L.G. Ferreira, F.C.D. Silva, M.M. Bastos, M.D.S. Costa, M.C.S. Lourenco, A.C. Pinto, A.U. Krettli, A.C. Aguiar, B.M. Teixeira, N.V.D. Silva, P.R.C. Martins, F.A.F.M. Bezerra, A.L.S. Camilo, G.P.D. Silva, and C.C.P. Costa Journal of Medicinal Chemistry 54 2011 5988 5999
5. M. Asadi, C.W. Oo, R.S. Kumar, H. Osman, and M. Ashraf Ali Acta Poloniae Pharmaceutica - Drug Research 70 2013 221 228
6. A. De Logu, V. Onnis, B. Saddi, C. Congiu, M.L. Schivo, and M.T. Cocco Journal of Antimicrobial Chemotherapy 49 2002 275 282
7. L. Bukowski, M. Janowiec, Z. Zwolska-Kwiek, and Z. Andrzejczyk Pharmazie 54 1999 651 654
8. M. Shaharyar, A.A. Siddiqui, M.A. Ali, D. Sriram, and P. Yogeeswari Bioorganic & Medicinal Chemistry Letters 16 2006 3947 3949
9. M.R. Shiradkar, M.K. Kumar, H.R. Gangadasu, T. Suresh, C.A. Kalyan, D. Panchal, Ranjit Kaur, B. Prashant, G. Jyoti, M. Vinod, and M. Raut Bioorganic & Medicinal Chemistry 15 2007 3997 4008
10. E. Petrlikova, K. Waisser, H. Divisova, P. Husakova, P. Vrabcova, J. Kunes, K. Kolar, and J. Stolarikova Bioorganic & Medicinal Chemistry 18 2010 8178 8187
11. G. Turan-Zitouni, Z.A. Kaplancikli, and A. Ozdemir European Journal of Medicinal Chemistry 45 2010 2085 2088
12. G.T. Zitouni, A. Ozdemir, Z.A. Kaplancikli, K. Benkli, P. Chevallet, and G. Akalin European Journal of Medicinal Chemistry 43 2008 981 985
13. N. Siddiqui, S.K. Arya, W. Ahsanb, and B. Azad International Journal of Drug Development & Research 3 2011 156 164
14. M. Shiradkar, G.V.S. Kumar, V. Dasari, S. Tatikonda, K.C. Akula, and R. Shah European Journal of Medicinal Chemistry 42 2007 807 816
15. G.V.S. Kumar, Y.R. Prasad, B.P. Mallikarjuna, and S.M. Chandrashekar European Journal of Medicinal Chemistry 45 2010 5120 51299
16. R. Sharma, P. Samadhiya, S.D. Srivastava, and S.K. Srivastava Journal of the Serbian Chemical Society 77 2012 17 26
17. T.D. Bradshaw, M.C. Bibby, J.A. Double, I. Fichtner, P.A. Cooper, M.C. Alley, S. Donohue, S.F. Stinson, J.E. Tomaszewjski, E.A. Sausville, and M.F.G. Stevens Molecular Cancer Therapeutics 1 2002 239 246
18. T.D. Bradshaw, M.S. Chua, H.L. Browne, V. Trapani, E.A. Sausville, and M.F.G. Stevens British Journal of Cancer 86 2002 1348 1354
19. I. Hutchinson, S.A. Jennings, B.R. Vishnu vajjala, A.D. Westwell, and M.F.G. Stevens Journal of Medicinal Chemistry 45 2002 744 747
20. I. Hutchinson, M.S. Chua, H.L. Browne, V. Trapani, T.D. Bradshaw, A.D. Westwell, and M.F.G. Stevens Journal of Medicinal Chemistry 44 2001 1446 1455
21. E. Kashiyama, I. Hutchinson, M.S. Chua, F. Sherman, Stinson, and R. Lawrence Journal of Medicinal Chemistry 42 1999 4172 4184
22. V. Benetau, T. Besson, J. Guillard, S. Leonce, and B. Pfeiffer European Journal of Medicinal Chemistry 34 1999 1053 1060
23. M.A. El-Sherbeny Arzeneim-Forsch 50 2000 843 847
24. L. Racane, V. Tralic-Kulenovic, L. Fiser-Jakic, D.W. Boykin, and G. Karminski-Zamola Heterocycles 55 2001 2085 2098
25. Mahmood-ul-Hasan, Z.H. Chohan, and C.T. Supuran Main Group Metal Chemistry 25 2002 291 296
26. N.B. Patel, R.H. Khan, and S.D. Rajani European Journal of Medicinal Chemistry 45 2010 4293 4299
27. P. Vicini, A. Geronikaki, M. Incerti, B. Busonera, Graziella Poni, C.A. Cabras, and P.L. Coll Bioorganic & Medicinal Chemistry 11 2003 4785 4789
28. V.N. Telvekar, V.K. Bairwa, K. Satardekar, and A. Bellubi Bioorganic & Medicinal Chemistry Letters 22 2012 649 652
29. V. Makarov, G. Manina, K. Mikusova, U. Mollmann, O. Ryabova, B.S. Joanis, N. Dhar, M.R. Pasca, S. Buroni, A.P. Lucarelli, A. Milano, E. De Rossi, M. Belanova, A. Boboyska, P. Dianiskova, J. Kordulakova, C. Sala, E. Fullam, P. Schneider, J.D. McKinney, P. Brodin, T. Christophe, S. Waddell, P. Butcher, J. Albrethsen, I. Rosenkrands, R. Brosch, V. Nandi, S. Bharath, S. Gaonkar, R.K. Shandil, V. Balasubramanian, T. Balganesh, S. Tyagi, J. Grosset, G. Riccardi, and S.T. Cole Science 324 2009 801 804
30. S.M. Batt, T. Jabeen, V. Bhowruth, L. Quill, P.A. Lund, L. Eggeling, L.J. Alderwick, K. Fütterer, and G.S. Besra PNAS 109 2012 11354 11359
31. Feng Wang, D. Sambandan, R. Halder, J. Wang, S.M. Batt, B. Weinrick, I. Ahmad, P. Yang, Y. Zhang, John Kim, M. Hassani, S. Huszar, C. Trefzer, Z. Ma, T. Kaneko, K.E. Mdluli, S. Franzblau, A.K. Chatterjee, K. Johnson, K. Mikusova, G.S. Besra, K. Fütterer, W.R. Jacobs Jr., and P.G. Schultza PNAS 110 2013 E2510 E2517
32. M.S. Costa, N. Boechat, E.A. Rangel, F.C. da Silva, A.M.T. de Souza, C.R. Rodrigues, H.C. Castro, I.N. Junior, M.C.S. Lourenco, S.M.S.V. Wardell, and V.F. Ferreira Bioorganic & Medicinal Chemistry 14 2006 8644 8653
33. S. Shafi, M.M. Alam, M. Naveen, M. Chaitanya, G. Vanaja, M.K. Arunasree, P. Reddanna, and M.S. Alam European Journal of Medicinal Chemistry 49 2012 324 333
34. S. Biswal, U. Sahoo, S. Sethy, H.K.S. Kumari, and M. Banarjee Asian Journal of Pharmaceutical and Clinical Research 5 2012 1 6 (and references cited therein)
35. S.G. Agalave, R.S. Maujan, and V.S. Pore Chemistry - An Asian Journal 6 2011 2696 2718
36. R. Maccari, R. Ottana, F. Monforte, and M.G. Vigorita Antimicrobial Agents and Chemotherapy 46 2002 294 299
37. R.J. Wallace, D.R. Nash, L.C. Steele, and V. Steingrube Journal of Clinical Microbiology 24 1986 976 981
38. J. Luna-Herrera, M.V. Reddy, and P.R.J. Gangadharam Antimicrobial Agents and Chemotherapy 39 1995 440 444
39. L. Heifets Drug susceptibility tests in the management of chemotherapy of tuberculosis L.B. Heifets, Drug Susceptibility in the Chemotherapy of Mycobacterial Infections 1998 CRC Press Boca Raton, FL 89 115
40. S.M. Batt, T. Jabeen, V. Bhowruth, L. Quill, P.A. Lund, L. Eggeling, L.J. Alderwick, K. Futtere, and G.S. Besra Proceedings of the National Academy of Sciences of the United States of America 109 2012 11354 11359
41. B. Hess, C. Kutzner, D. Vander Spoel, and E. Lindhal Gromacs Journal of Chemical Theory and Computation 4 2008 435 447
42. A.W. Schuettellkopf, and D.M. Van Aalten Acta Crystallographica 60 2004 1355 1363
43. G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner, R.K. Belew, D.S. Goodsell, and A.J. Olson Journal of Computational Chemistry 16 2009 2785 2791
44. W.L. DeLano The Pymol Molecular Graphics System 2006 Delano Scientific San Carlos, CA, USA http://www.pymol.org