Synthesis, anti-tuberculosis activity and 3D-QSAR study of amino acid conjugates of 4-(adamantan-1-yl) group containing quinolines

European Journal of Medicinal Chemistry

Volumn 44, Issue 5, 2009, Pages 2017-2029

  Nayyar, Amit ^a   Patel, Sanjay R ^a   Shaikh, Mushtaque ^b   Coutinho, Evans ^b   Jain, Rahul ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

^b BOMBAY COLLEGE OF PHARMACY   (India)

Author keywords

Amino acid conjugates; Anti tuberculosis; CoMFA; Ring substituted quinolines; Tuberculosis

Indexed keywords

4 ADAMANTAN 1 YL QUINOLINE 2 CARBOXYLIC ACID N' (2 AMINO 3 METHYL PENTANOYL)HYDRAZIDE; 4 ADAMANTAN 1 YL QUINOLINE 2 CARBOXYLIC ACID N' (2 AMINO 3 PHENYLPROPIONYL)HYDRAZIDE; 4 ADAMANTAN 1 YL QUINOLINE 2 CARBOXYLIC ACID N' (2 AMINO 4 METHYL PENTANOYL)HYDRAZIDE; 4 ADAMANTAN 1 YL QUINOLINE 2 CARBOXYLIC ACID N' (2 AMINO 4 METHYLSULFANYL BUTYRYL)HYDRAZIDE; 4 ADAMANTAN 1 YL QUINOLINE 2 CARBOXYLIC ACID N' (2 AMINOACETYL)HYDRAZIDE; 4 ADAMANTAN 1 YL QUINOLINE 2 CARBOXYLIC ACID N' (2 AMINOPROPIONYL)HYDRAZIDE; 4 ADAMANTAN 1 YL QUINOLINE 2 CARBOXYLIC ACID N' (2,5 DIAMINOPENTANOYL)HYDRAZIDE; 4 ADAMANTAN 1 YL QUINOLINE 2 CARBOXYLIC ACID N' (2,6 DIAMINOHEXANOYL)HYDRAZIDE; 4 ADAMANTAN 1 YL QUINOLINE 2 CARBOXYLIC ACID N' [2 AMINO 3 (1H IMIDAZOL 4 YL)PROPIONYL]HYDRAZIDE; 4 ADAMANTAN 1 YL QUINOLINE 2 CARBOXYLIC ACID N' [2 AMINO 3 (1H INDOL 2 YL)PROPIONYL]HYDRAZIDE; 4 ADAMANTAN 1 YL QUINOLINE 2 CARBOXYLIC ACID N' [2 AMINO 3 (4 HYDROXYPHENYL)PROPIONYL]HYDRAZIDE; 5 [N' (4 ADAMANTAN 1 YL QUINOLINE 2 CARBONYL)HYDRAZINO] 4 AMINO 5 OXOPENTANOIC ACID AMIDE; [1 [N' (4 ADAMANTAN 1 YL QUINOLINE 2 CARBONYL)HYDRAZINOCARBONYL] 2 METHYLBUTYL]CARBAMIC ACID TERT BUTYL ESTER; [1 [N' (4 ADAMANTAN 1 YL QUINOLINE 2 CARBONYL)HYDRAZINOCARBONYL] 3 CARBAMOYLPROPYL]CARBAMIC ACID TERT BUTYL ESTER; [1 [N' (4 ADAMANTAN 1 YL QUINOLINE 2 CARBONYL)HYDRAZINOCARBONYL] 3 METHYLBUTYL]CARBAMIC ACID TERT BUTYL ESTER; [1 [N' (4 ADAMANTAN 1 YL QUINOLINE 2 CARBONYL)HYDRAZINOCARBONYL] 3 METHYLSULFANYLPROPYL]CARBAMIC ACID TERT BUTYL ESTER; [1 [N' (4 ADAMANTAN 1 YL QUINOLINE 2 CARBONYL)HYDRAZINOCARBONYL] 4 (N,N' BIS BENZYLOXYCARBONYLGUANIDINOBUTYL)]CARBAMIC ACID TERT BUTYL ESTER; [2 [N' (4 ADAMANTAN 1 YL QUINOLINE 2 CARBONYL)HYDRAZINO] 1 (1H IMIDAZOL 4 YL METHYL) 2 OXOETHYL]CARBAMIC ACID TERT BUTYL ESTER; [2 [N' (4 ADAMANTAN 1 YL QUINOLINE 2 CARBONYL)HYDRAZINO] 1 (1H INDOL 2 YL METHYL) 2 OXOETHYL]CARBAMIC ACID TERT BUTYL ESTER; [2 [N' (4 ADAMANTAN 1 YL QUINOLINE 2 CARBONYL)HYDRAZINO] 1 (4 BENZYLOXY BENZYL) 2 OXOETHYL]CARBAMIC ACID TERT BUTYL ESTER; [2 [N' (4 ADAMANTAN 1 YL QUINOLINE 2 CARBONYL)HYDRAZINO] 1 BENZYL 2 OXOETHYL]CARBAMIC ACID TERT BUTYL ESTER; [2 [N' (4 ADAMANTAN 1 YL QUINOLINE 2 CARBONYL)HYDRAZINO] 1 METHYL 2 OXOETHYL]CARBAMIC ACID TERT BUTYL ESTER; [2 [N' (4 ADAMANTAN 1 YL QUINOLINE 2 CARBONYL)HYDRAZINO] 2 OXOETHYL]CARBAMIC ACID TERT BUTYL ESTER; [5 [N' (4 ADAMANTAN 1 YL 2 CARBONYL)HYDRAZINO] 4 AMINO 5 OXOPENTYL]GUANIDINE; [5 [N' (4 ADAMANTAN 1 YL QUINOLINE 2 CARBONYL)HYDRAZINO] 4 TERT BUTOXY CARBONYLAMINO 5 OXOPENTYL]CARBAMIC ACID TERT BUTYL ESTER; [6 [N' (4 ADAMANTAN 1 YL QUINOLINE 2 CARBONYL)HYDRAZINO] 5 TERT BUTOXY CARBONYLAMINO 6 OXOHEXYL]CARBAMIC ACID BENZYL ESTER; N2 [4 AMINO(IMINO)METHYLAMINO 1 HYDRAZINOCARBONYLBUTYL] 4 (ADAMANTAN 1 YL) 2 QUINOLINECARBOXAMIDE; QUINOLINE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ARTICLE; COMPARATIVE MOLECULAR FIELD ANALYSIS; DRUG ACTIVITY; DRUG CONJUGATION; DRUG SYNTHESIS; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

AMINO ACIDS; ANTITUBERCULAR AGENTS; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUINOLINES;

EID: 62549144843     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.10.004     Document Type: Article

References (24)

1. World Health Organization, Tuberculosis Fact Sheet, No. 104, 2007; please see: .
2. Nayyar A., and Jain R. Curr. Med. Chem. 12 (2005) 1873-1886
3. Ballell L., Field R.A., Duncan K., and Young R.J. Antimicrob. Agents Chemother. 49 (2005) 2153-2163
4. Janin Y.L. Bioorg. Med. Chem. 15 (2007) 2479-2513
5. Jain R., Vaitilingam B., Nayyar A., and Palde P.B. Bioorg. Med. Chem. Lett. 13 (2003) 1051-1054
6. Vangapandu S., Jain M., Jain R., Kaur S., and Singh P.P. Bioorg. Med. Chem. 12 (2004) 2501-2508
7. Monga V., Nayyar A., Vaitilingam B., Palde P.B., Jhamb S.S., Singh P.P., and Jain R. Bioorg. Med. Chem. 12 (2004) 6465-6472
8. Nayyar A., Malde A., Coutinho E., and Jain R. Bioorg. Med. Chem. 14 (2006) 847-856
9. Nayyar A., Malde A., Coutinho E., and Jain R. Bioorg. Med. Chem. 14 (2006) 7302-7310
10. Nayyar A., Monga V., Malde A., Coutinho E., and Jain R. Bioorg. Med. Chem. 15 (2007) 626-640
11. Yang G.F., and Huang X. Curr. Pharm. Des. 12 (2006) 4601-4611
12. Prado-Prado F.J., González-Díaz H., Santana L., and Uriarte E. Bioorg. Med. Chem. 15 (2007) 897-902
13. González-Díaz H., Pérez-Bello A., Uriarte E., and González-Díaz Y. Bioorg. Med. Chem. Lett. 16 (2006) 547-553
14. Bagchi M.C., Mills D., and Basak S.C. J. Mol. Model. 13 (2007) 111-120
15. Hevener K.E., Ball D.M., Buolamwini J.K., and Lee R.E. Bioorg. Med. Chem. 16 (2008) 8042-8053
16. Franzblau S.G., Witzig R.S., McLaughlin J.C., Torres P., Madico G., Herandez A., Degnan M.T., Cook M.B., Quenzer V.K., Ferguson R.M., and Gilman R.H. J. Clin. Microbiol. 36 (1998) 362-366
17. Collins L., and Franzblau S.G. Antimicrob. Agents Chemother. 41 (1997) 1004-1009
18. Cramer R.D., Patterson D.E., and Bunce J.D. J. Am. Chem. Soc. 110 (1988) 5959-5967
19. Martin E.J., Blaney J.M., Siani M.A., Spellmeyer D.C., Wong A.K., and Moos W.H. J. Med. Chem. 38 (1995) 1431-1436
20. CoMFA and QSAR Manual, Sybyl 7.1, Associates Inc., 1699 S Hanley Rd., St. Louis, MO 631444, USA.
21. Sybyl v.7.1 Tripos Inc., USA.
22. Liu M.L., Diu J.M., Li D.C., and Wang D.Q. Acta Crystallogr. E 62 (2006) o1009-o1100
23. InsightII, Version 2005L (2005), Accelrys, Inc., San Diego, CA, USA
24. Maple J.R., Hwang M.-J., Stockfisch T.P., Dinur U., Waldman M., Ewig C.S., and Hagler A.T. J. Comput. Chem. 15 (1994) 162-182