Schiff bases of indoline-2,3-dione (isatin) derivatives and nalidixic acid carbohydrazide, synthesis, antitubercular activity and pharmacophoric model building

European Journal of Medicinal Chemistry

Volumn 45, Issue 10, 2010, Pages 4578-4586

  Aboul Fadl, Tarek ^a   Bin Jubair, Fayzah A S ^a   Aboul Wafa, Omima ^a  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

Antitubercular activity; Isatin derivatives; MOE; Nalidixic acid carbohydrazide; Pharmacophore; Schiff bases

Indexed keywords

1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO N' (2 OXO 1 PROPYLINDOLIN 3 YLIDENE) 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; 1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO N' (2 OXOINDOLIN 3 YLIDENE) 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; 1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO N' [2 OXO 1 [(PIPERIDIN 1 YL)METHYL]INDOLIN 3 YLIDENE] 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; 1 ETHYL 1,4 DIHYDRO 7 METHYL N' (1 METHYL 2 OXOINDOLIN 3 YLIDENE) 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; 1 ETHYL 1,4 DIHYDRO 7 METHYL N' [4 [(METHYLPIPERAZIN 1 YL)METHYL] 2 OXOINDOLIN 3 YLIDENE] 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; 1 ETHYL 1,4 DIHYDRO N' (1 HYDROXYMETHYL 2 OXOINDOLIN 3 YLIDENE) 7 METHYL 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; 1 ETHYL N' (1 ETHYL 2 OXOINDOLIN 3 YLIDENE) 1,4 DIHYDRO 7 METHYL 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; ISATIN DERIVATIVE; ISONIAZID; N' (1 ALLYL 2 OXOINDOLIN 3 YLIDENE) 1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; N' (1 ALLYL 5 BROMO 2 OXOINDOLIN 3 YLIDENE) 1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; N' (1 BENZYL 2 OXOINDOLIN 3 YLIDENE) 1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; N' (1 BENZYL 5 BROMO 2 OXOINDOLIN 3 YLIDENE) 1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; N' (5 BROMO 1 ETHYL 2 OXOINDOLIN 3 YLIDENE) 1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; N' (5 BROMO 1 HYDROXYMETHYL 2 OXOINDOLIN 3 YLIDENE) 1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; N' (5 BROMO 1 METHYL 2 OXOINDOLIN 3 YLIDENE) 1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; N' (5 BROMO 2 OXO 1 PROPYLINDOLIN 3 YLIDENE) 1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; N' (5 BROMO 2 OXOINDOLIN 3 YLIDENE) 1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; N' [1 [(DIETHYLAMINO)METHYL] 2 OXOINDOLIN 3 YLIDENE] 1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; N' [1 [(DIETHYLAMINO)METHYL] 5 BROMO 2 OXOINDOLIN 3 YLIDENE] 1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; N' [5 BROMO 1 [(4 METHYLPIPERAZIN 1 YL)METHYL] 2 OXOINDOLIN 3 YLIDENE] 1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; N' [5 BROMO 2 OXO 1 [(PIPERIDIN 1 YL)METHYL] INDOLIN 3 YLIDENE] 1 ETHYL 1,4 DIHYDRO 7 METHYL 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOHYDRAZIDE; NALIDIXIC ACID; SCHIFF BASE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL STRAIN; DRUG ACTIVITY; DRUG DESIGN; DRUG SYNTHESIS; HYDROGEN BOND; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM; MYCOBACTERIUM CHELENEO; MYCOBACTERIUM INTERCELLULARI; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM XENOPEI; NONHUMAN; PHARMACOPHORE; SPECTROSCOPY; STRUCTURE ANALYSIS;

ANTITUBERCULAR AGENTS; DRUG DESIGN; HUMANS; HYDRAZINES; ISATIN; MODELS, MOLECULAR; MYCOBACTERIUM; NALIDIXIC ACID; SCHIFF BASES; TUBERCULOSIS;

EID: 77956186832     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.07.020     Document Type: Article

References (24)

1. Global alliance for TB drug development Available from: http://www.tballiance.org/home/home.php (accessed 08.07.10)
2. C. Dye Lancet 367 2006 938 940
3. Tuberculosis (TB)WHO extensively drug-resistant tuberculosis Available from: http://www.who.int/tb/challenges/xdr/en/index.html (accessed 08.07.10)
4. M. McCarthy Lancet 348 1996 393
5. S.E. Dorman, and R.E. Chaisson Nat. Med. 13 2007 295 298
6. T.D. Primm, and S.G. Franzblau Curr. Bioact. Compd. 3 2007 1 8
7. MÉ DICINS SANS FRONTIE' RES. Available from: upload/uploads/ rapports/2006-10-30-tb/Thttp://www.msf.ch/fileadmin/user-BPipeline.pdf. (accessed 08.07.10).
8. M.A. Hussein, T. Aboul-Fadl, and A. Hussein Bull. Pharm. Sci. Assiut Univ. 28 2005 131 136
9. L. Ballell, R.A. Field, K. Duncan, and R.J. Young Antimicrob. Agents Chemother. 49 2005 2153 2163
10. D. Sriram, P. Yogeeswari, J.S. Basha, D.R. Radhab, and V. Nagarajab Bioorg. Med. Chem. 13 2005 5774 5778
11. M. Oblak, S.G. Grdadolnik, M. Kotnik, R. Jerala, M. Filipi, and T. olmajer Bioorg. Med. Chem. Lett. 15 2005 5207 5210
12. A. Maxwell Biochem. Soc. Trans. 27 1999 48 53
13. T. Aboul-Fadl, F.A. Mohammed, and E.A. Hassan Arch. Pharm. Res. 26 2003 778 784
14. N. Karal, A. Gürsoy, F. Kandemirli, N. Shvets, F.B. Kaynak, S. Özbey, V. Kovalishyn, and V. Dimoglo Bioorg. Med. Chem. 15 2007 5888 5904
15. A.F. Youssef, F.A. Omar, H.A. Elsherief, and G.E.A.A. Abuo-Rahma Bull. Pharm. Sci. Assiut Univ. 21 1998 15 26
16. D. Sriram, A. Aubry, P. Yogeeswari, and L.M. Fisher Bioorg. Med. Chem. Lett. 16 2006 2982 2985
17. NCCLS Susceptibility Testing of Mycobacteria, Nocardia, and Other Aerobic Actinomycetes; Tentative Standard NCCLS document M24-T2 [ISBN 1-56238-423-6] second ed. 2000 NCCLS, 960 West Valley Road, Suite1400 Wayne, PA 19087-1898, USA
18. W.S. Abdel-Aal, H.Y. Hassan, T. Aboul-Fadl, and A.F. Youssef Eur. J. Med. Chem. 45 2010 1098 1106
19. J.S. Mason, A.C. Good, and E.J. Martin Curr. Pharm. Des. 7 2001 567 597
20. T. Langer, and G. Wolber Drug Discov. Today (Technologies) 1 2004 203 207
21. Manual of Molecular Operating Environment (MOE) Version 2007.09 2007 Chemical Computing Group Inc. Montreal, Quebec, Canada
22. A.E. Esmaili, and A. Bodaghi Tetrahedron 59 2003 1169 1171
23. A.R. Katritzky, W.Q. Fan, D.S. Liang, and Q.L. Li J. Heterocyclic Chem. 26 1989 1541 1545
24. A. Stankevicius, L. Mazilis, V. Garaliene, and S. Riselis Khimiko-Farmatsevticheskii Zhurnal 15 1981 31 34