Development of novel tetrahydrothieno[2,3-c]pyridine-3-carboxamide based Mycobacterium tuberculosis pantothenate synthetase inhibitors: Molecular hybridization from known antimycobacterial leads

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 6, 2014, Pages 1938-1947

  Samala, Ganesh ^a   Devi, Parthiban Brindha ^a   Nallangi, Radhika ^a   Sridevi, Jonnalagadda Padma ^a   Saxena, Shalini ^a   Yogeeswari, Perumal ^a   Sriram, Dharmarajan ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

Author keywords

Cytotoxicity; Pantothenate synthetase; Tuberculosis

Indexed keywords

1 BENZOYL N (4 NITROPHENYL) 3 PHENYL 6,7 DIHYDRO 1H PYRAZOLO[4,3 C]PYRIDINE 5(4H) CARBOXAMIDE; 2 (5 NITROFURAN 2 CARBOXAMIDO) 6 (4 NITROPHENYLSULFONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 ACETYLPHENYLSULFONYL) 2 (5 NITROTHIOPHENE 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 BROMOPHENYLSULFONYL) 2 (5 NITROTHIOPHENE 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 CHLOROPHENYLCARBAMOTHIOYL) 2 (5 NITROFURAN 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 CHLOROPHENYLCARBAMOTHIOYL) 2 (5 NITROTHIOPHENE 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 CHLOROPHENYLCARBAMOYL) 2 (5 NITROFURAN 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 CHLOROPHENYLCARBAMOYL) 2 (5 NITROTHIOPHENE 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 FLUOROPHENYLCARBAMOTHIOYL) 2 (5 NITROFURAN 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 FLUOROPHENYLCARBAMOTHIOYL) 2 (5 NITROTHIOPHENE 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 FLUOROPHENYLSULFONYL) 2 (5 NITROTHIOPHENE 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 METHOXYLPHENYLSULFONYL) 2 (5 NITROTHIOPHENE 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 METHOXYPHENYLCARBAMOYL) 2 (5 NITROFURAN 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 METHOXYPHENYLCARBAMOYL) 2 (5 NITROTHIOPHENE 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 NITROPHENYLCARBAMOTHIOYL) 2 (5 NITROTHIOPHENE 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 NITROPHENYLCARBAMOYL) 2 (5 NITROFURAN 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 NITROPHENYLCARBAMOYL) 2 (5 NITROTHIOPHENE 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (4 NITROPHENYLSULFONYL) 2 (5 NITROTHIOPHENE 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (BENZYLCARBAMOTHIOYL) 2 (5 NITROTHIOPHENE 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (BENZYLCARBAMOYL) 2 (5 NITROFURAN 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; 6 (BENZYLCARBAMOYL) 2 (5 NITROTHIOPHENE 2 CARBOXAMIDO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBOXAMIDE; AMIDE; ETHAMBUTOL; ISONIAZID; PANTOTHENATE SYNTHETASE; SID 92097880; SYNTHETASE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG; 6-(4-NITROPHENYLSULFONYL)-2-(5-NITROTHIOPHENE-2-CARBOXAMIDO)-4,5,6,7-TETRAHYDROTHIENO(2,3-C)PYRIDINE-3-CARBOXAMIDE; ENZYME INHIBITOR; PEPTIDE SYNTHASE; SULFONAMIDE; THIOPHENE DERIVATIVE;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ARTICLE; BINDING AFFINITY; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYTOTOXICITY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG DESIGN; DRUG STRUCTURE; ENZYME INHIBITION; IN VITRO STUDY; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; MOLECULAR HYBRIDIZATION; MOUSE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; ENZYMOLOGY; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

MYCOBACTERIUM TUBERCULOSIS;

ANTITUBERCULAR AGENTS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; ENZYME INHIBITORS; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; PEPTIDE SYNTHASES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; THIOPHENES;

EID: 84896735414     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.01.030     Document Type: Article

References (15)

1. C. Dye, S. Scheele, P. Dolin, V. Pathania, and M.C. Raviglione J. Am. Med. Assoc. 282 1999 677
2. E. Stokstad Science 287 2000 239
3. J.B. Lynch Med. Clin. North Am. 97 2013 553
4. J.C. Palomino, and A. Martin Curr. Med. Chem. 20 2013 3785
5. I. Tsuyuguchi Tuberculosis 81 2001 221
6. W.K. Merkel, and B.P. Nichols FEMS Microbiol. Lett. 143 1996 247
7. R. Zheng, and J.S. Blanchard Biochemistry 40 2001 12904
8. S. Wang, and D. Eisenberg Protein Sci. 12 2003 1097
9. G. Samala, P.B. Devi, R. Nallangi, P. Yogeeswari, and D. Sriram Eur. J. Med. Chem. 69 2013 356
10. S. Velaparthi, M. Brunsteiner, R. Uddin, B. Wan, S.G. Franzblau, and P.A. Petukhov J. Med. Chem. 51 2008 1999
11. Y. Yang, P. Gao, Y. Liu, X. Ji, M. Gan, Y. Guan, X. Hao, Z. Li, and C. Xiao Bioorg. Med. Chem. Lett. 21 2011 3943
12. E.L. White, K. Southworth, L. Ross, S. Cooley, R.B. Gill, M.I. Sosa, A. Manouvakhova, L. Rasmussen, C. Goulding, D. Eisenberg, and T.M. Fletcher J. Biomol. Screen. 12 2007 100
13. A.W. Hung, H.L. Silvestre, S. Wen, A. Ciulli, T.L. Blundell, and C. Abell Angew. Chem. 48 2009 8452
14. R.C. Reynolds, S. Ananthan, E. Faaleolea, J.V. Hobrath, C.D. Kwong, C. Maddox, L. Rasmussen, M.I. Sosa, E. Thammasuvimol, E.L. White, W. Zhang, and J.A. Secrist III Tuberculosis 92 2012 72
15. Y. Huang, and A. Dömling Mol. Divers. 15 2011 3