Synthesis and antibacterial evaluation of a novel series of 2-(1,2-dihydro-3-oxo-3H-pyrazol-2-yl)benzothiazoles

Chemistry and Biodiversity

Volumn 8, Issue 2, 2011, Pages 253-265

  Stella, Alessandro ^a   Segers, Kenneth ^a   De Jonghe, Steven ^a   Vanderhoydonck, Bart ^a   Rozenski, Jef ^a   Anné, Jozef ^a   Herdewijn, Piet ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Antibacterial activity; Benzothiazoles, 2 (3 oxopyrazol 2 yl) ; Structure activity relationship (SAR)

Indexed keywords

1,2 DIHYDRO 2 (6 METHOXYBENZOTHIAZOL 2 YL) 5 METHYL 3H PYRAZOL 3 ONE; 1,2 DIHYDRO 2 (6 METHOXYBENZOTHIAZOL 2 YL) 5 METHYL 4 PHENYL 3H PYRAZOL 3 ONE; 1,2 DIHYDRO 5 METHYL 2 (6 METHYLBENZOTHIAZOL 2 YL) 3H PYRAZOL 3 ONE; 1,2 DIHYDRO 5 METHYL 2 (6 METHYLBENZOTHIAZOL 2 YL) 4 PHENYL 3H PYRAZOL 3 ONE; 2 (1,2 DIHYDRO 3 OXO 3H PYRAZOL 2 YL)BENZOTHIAZOLE DERIVATIVE; 2 (4 CHLOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 METHYL 4 PHENYL 3H PYRAZOL 3 ONE; 2 (4,6 DIFLUOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 METHYL 3H PYRAZOL 3 ONE; 2 (4,6 DIFLUOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 METHYL 4 PHENYL 3H PYRAZOL 3 ONE; 2 (5 CHLOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 4,5 DIMETHYL 3H PYRAZOL 3 ONE; 2 (5 CHLOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 (1 METHYLETHYL) 3H PYRAZOL 3 ONE; 2 (5 CHLOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 METHYL 3H PYRAZOL 3 ONE; 2 (5 CHLOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 METHYL 4 PHENYL 3H PYRAZOL 3 ONE; 2 (5 CHLOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 PHENYL 3H PYRAZOL 3 ONE; 2 (5,6 DIMETHYLBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 METHYL 3H PYRAZOL 3 ONE; 2 (5,6 DIMETHYLBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 METHYL 4 PHENYL 3H PYRAZOL 3 ONE; 2 (6 CHLOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 4,5 DIMETHYL 3H PYRAZOL 3 ONE; 2 (6 CHLOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 (1 METHYLETHYL) 3H PYRAZOL 3 ONE; 2 (6 CHLOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 METHYL 3H PYRAZOL 3 ONE; 2 (6 CHLOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 METHYL 4 (1 METHYLETHYL) 3H PYRAZOL 3 ONE; 2 (6 CHLOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 METHYL 4 PHENYL 3H PYRAZOL 3 ONE; 2 (6 CHLOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 PHENYL 3H PYRAZOL 3 ONE; 2 (6 CHLOROBENZOTHIAZOL 2 YL) 4 ETHYL 1,2 DIHYDRO 5 METHYL 3H PYRAZOL 3 ONE; 2 (6 FLUOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 METHYL 3H PYRAZOL 3 ONE; 2 (6 FLUOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 METHYL 4 PHENYL 3H PYRAZOL 3 ONE; 2 (BENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 METHYL 3H PYRAZOL 3 ONE; 4 BENZYL 2 (6 CHLOROBENZOTHIAZOL 2 YL) 1,2 DIHYDRO 5 METHYL 3H PYRAZOL 3 ONE; ANTIINFECTIVE AGENT; BENZOTHIAZOLE DERIVATIVE; GENTAMICIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; ESCHERICHIA COLI; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; SALMONELLA TYPHIMURIUM; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; BENZOTHIAZOLES; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MICROBIAL SENSITIVITY TESTS; PYRAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP;

STAPHYLOCOCCUS AUREUS;

EID: 79951925243     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.201000241     Document Type: Article

References (13)

1. C. Walsh, Nat. Rev. Microbiol. 2003, 1, 65.
2. J. D. Peterson, L. A. Umayam, T. Dickinson, E. K. Hickey, O. White, Nucleic Acids Res. 2001, 29, 123.
3. D. J. Payne, M. N. Gwynn, D. J. Holmes, D. L. Pampliano, Nat. Rev. Drug Discovery 2007, 6, 29.
4. Y. Yin, L. Lin, C. Ruiz, M. D. Cameron, J. Pocas, W. Grant, T. Schröter, W. Chen, D. Duckett, S. Schürer, P. LoGrasso, Y. Feng, Bioorg. Med. Chem. Lett. 2009, 19, 6686.
5. C. B. Vu, J. C. Milne, D. P. Carney, J. Song, W. Choy, P. D. Lambert, D. J. Gagne, M. Hirsch, A. Cote, M. Davis, E. Lainez, N. Meade, K. Normington, M. R. Jirousek, R. B. Perni, Bioorg. Med. Chem. Lett. 2009, 19, 1416.
6. M. Anzini, A. Chelini, A. Mancini, A. Cappelli, M. Frosini, L. Ricci, M. Valoti, J. Magistretti, L. Castelli, A. Giordani, F. Makovec, S. Vomero, J. Med. Chem. 2010, 53, 734.
7. E. Y. Song, N. Kaur, M.-Y. Park, Y. Jin, K. Lee, G. Kim, K. Y. Lee, J. S. Yang, J. H. Shin, K.-Y. Nam, K. T. No, G. Han, Eur. J. Med. Chem. 2008, 43, 1519.
8. R. Aggarwal, V. Kumar, P. Tyagi, S. P. Singh, Bioorg. Med. Chem. 2006, 14, 1785.
9. T. I. Moy, A. L. Conery, J. Larkins-Ford, G. Wu, R. Mazitschek, G. Casadei, K. Lewis, A. E. Carpenter, F. M. Ausubel, ACS Chem. Biol. 2009, 4, 527.
10. W.-B. Chen, G.-Y. Jin, Heteroatom Chem. 2001, 12, 151.
11. N. P. Peet, S. Sunder, R. J. Barbuch, M. R. Whalon, J. C. Huffman, J. Heterocycl. Chem. 1988, 25, 543.
12. S. Guillou, F. J. Bonhomme, Y. L. Janin, Synthesis 2008, 3504.
13. European Committee on Antimicrobial Susceptibility Testing (2003) Determination of minimum inhibitory concentrations (MICs) of antibacterial agents by broth microdilution, EUCAST Discussion Document E.Def 2003, 5.1, Clin. Microbiol Infect. 2003, 9 (issue 7 insert), pp. 1-10.