Quantitative structure-activity relationship (QSAR) of aryl alkenyl amides/imines for bacterial efflux pump inhibitors

European Journal of Medicinal Chemistry

Volumn 44, Issue 1, 2009, Pages 229-238

  Nargotra, A ^a   Koul, S ^a   Sharma, S ^a   Khan, I A ^a   Kumar, A ^a   Thota, N ^a   Koul, J L ^a   Taneja, S C ^a   Qazi, G N ^a  

^a CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

Author keywords

Aryl alkenyl amides imines; Efflux pump inhibitors; Genetic function algorithm; Potentiators; QSAR

Indexed keywords

ALKENYL GROUP; AMIDE; ANTIINFECTIVE AGENT; EFFLUX PUMP INHIBITOR; IMINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; MOLECULAR MODEL; NONHUMAN; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION; THERMODYNAMICS;

ALGORITHMS; AMIDES; BACTERIA; BACTERIAL PROTEINS; IMINES; MEMBRANE TRANSPORT PROTEINS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 57949095949     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.02.015     Document Type: Article

References (51)

1. Eliopoulus G.M. Drugs 49 Suppl. 2 (1995) 48-57
2. Gums G.M. Int. J. Antimicrob. Agents 22 (2003) S3-S13
3. Pan X.S., and Fisher M. Antimicrob. Agents Chemother. 41 (1997) 471-474
4. Pestova E., Millicap J.J., Noskin G.A., and Peterson L.R. J. Antimicrob. Chemother. 45 (2000) 583-590
5. Baranova N., and Neyfakh A.A. Antimicrob. Agents Chemother. 41 (1997) 1396-1398
6. Kaatz G.W., and Seo S.M. Antimicrob. Agents Chemother. 39 (1995) 2650-2655
7. Yoshida H., Bogaki M., Nakamura S., Ubukata K., and Konno M. J. Bacteriol. 172 (1990) 6942-6949
8. Lage H. Int. J. Antimicrob. Agents 22 (2003) 188-199
9. Lynch A.S. Biochem. Pharmacol. 71 (2006) 949
10. Schmitz F.J., Fluit A.C., Luckefahr M., Engler B., Hofmann B., Verhoef J., Heinz H.P., Hadding U., and Jones M.E. J. Antimicrob. Chemother. 42 (1998) 807
11. Poole K., and Lomovskaya O. Drug Discov. Today 3 (2006) 145
12. Khan I.A., Mirza Z.M., Kumar A., Verma V., and Qazi G.N. Antimicrob. Agents Chemother. 50 (2006) 810-812
13. Atal C.K., Dubey R.K., and Singh J. J. Pharmacol. Exp. Ther. 232 (1985) 258-262
14. Badmaev V., Majeed M., and Norkus E.P. Nutr. Res. 19 (1999) 381-388
15. Atal C.K., Zutshi U., and Rao P.G. J. Ethnopharmacol. 4 (1981) 229-232
16. Singh J., Dubey R.K., and Atal C.K. J. Pharmacol. Exp. Ther. 236 (1986) 488-493
17. Koul S., Koul J.L., Taneja S.C., Dhar K.L., Jamwal D.S., Reen R.K., and Singh J. Bioorg. Med. Chem. 8 (2000) 251-268
18. Bhardwaj R.K., Glaeser H., Becquemont L., Koltz U., Gupta S.K., and Fromm M.F. J. Pharmacol. Exp. Ther. 302 (2002) 645-650
19. S. Koul, J.L. Koul, S.C. Taneja, I.A. Khan, A. Kumar, A. Tikoo, M. Tikoo, R.K. Johri, V. Verma, G.N. Qazi, Aromatic substituted pentadienoic acid amides, their di- and tetrahydro derivatives for combination with anti-infective drugs, US Patent 2007/0004645, 04.01.2007.
20. Marder V.J. Blood Rev. 15 (2001) 143-157
21. Tuppurainen K. Chemosphere 38 (1999) 3015-3030
22. Hansch C., Kurup A., Garg R., and Gao H. Chem. Rev. 101 (2001) 619-672
23. Maloney P.P., Hansch C., Fujita T., and Muir R.M. Nature 194 (1962) 178-180
24. Fujita T., Iwasa J., and Hansch C. J. Am. Chem. Soc. 86 (1964) 5175-5180
25. Hansch C. Acc. Chem. Res. 2 (1969) 232-239
26. Livingstone D.J. J. Chem. Inf. Comput. Sci. 40 (2000) 195-209
27. Shi L.M., Fan Y., Myers T.G., Paull K.D., and Weinstein J.N. J. Chem. Inf. Comput. Sci. 38 (1998) 189-199
28. Oloff S., Mailman R.B., and Tropsha A. J. Med. Chem. 48 (2005) 7322-7332
29. Meneses-Marcel, Marrero-Ponce Y., Machado-Tugores Y., Montero-Torres A., Pereira D.M., Escario J.A., Nogal-Ruiz J.J., Ochoa C., Aran V.J., Martinez-Fernandez A.R., and Garcia Sanchez R.N. Bioorg. Med. Chem. Lett. 15 (2005) 3838-3843
30. Santana L., Uriarte E., Gonzalez-Diaz H., Zagotto G., Soto-Otero R., and Mendez-Alvarez E. J. Med. Chem. 49 (2006) 1149-1156
31. Deswal S., and Roy N. Eur. J. Med. Chem. 41 11 (2006) 1339-1346
32. Eliopoulus G.M., and Moellering R.C.J. Antimicrobial Combinations. In: Lorian V. (Ed). Antibiotics in Laboratory Medicine. fourth ed. (1996), The Williams & Wilkins Co., Baltimore, MD 330-396
33. Brenwald N.P., Gill M.J., and Wise R. Antimicrob. Agents Chemother. 42 (1998) 2032-2035
34. de Gregorio C., Kier L.B., and Hall L.H. J. Comput. Aided Mol. Des. 12 (1998) 557-561
35. Kier L.B., and Hall L.H. Pharm. Res. 7 (1990) 801-807
36. Rose K., Hall L.H., and Kier L.B. J. Chem. Inf. Comput. Sci. 42 (2002) 651-666
37. Melagraki G., Afantitis A., Sarimveis H., Igglessi-Markopoulou O., and Supuran C.T. Bioorg. Med. Chem. 14 4 (2006) 1108-1114
38. Estrada E., and Uriarte E. Curr. Med. Chem. 8 (2001) 1573-1588
39. Kier L.B., and Hall L.H. Molecular Connectivity in Chemistry and Drug Research (1976), Academic Press, New York
40. Kier L.B., and Hall L.H. Molecular Connectivity in Structure-Activity Analysis (1986), John Wiley Publ., London
41. Katritzky A.R., and Gordeeva E. J. Chem. Inf. Comput. Sci. 33 6 (1993) 835-857
42. www.accelrys.com.
43. Shi W., Shen Q., Kong W., and Bao-xian Y. Eur. J. Med. Chem. 42 1 (2007) 81-86
44. Rogers D., and Hopfinger A.J. J. Chem. Inf. Comput. Sci. 34 (1994) 854-866
45. Jaiswal M., Khadikar P.V., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 14 (2004) 3283-3290
46. Shapiro S., and Guggenheim B. Quant. Struct.-Act. Relat. 17 (1998) 327-337
47. Golbraikh A., and Tropsha A. J. Mol. Graph. Model. 20 (2002) 269-276
48. Roy P., and Roy K. QSAR Comb. Sci. 26 (2007). http://dx.doi.org/10.1002/qsar.200710043
49. Deswal S., and Roy N. Eur. J. Med. Chem. 42 4 (2007) 463-470 10.1016/j.ejmech.2006.09.011
50. Ghose A.K., and Crippen G.M. J. Comput. Chem. 7 (1986) 565-577
51. Ghose A.K., Viswanadhan V.N., Revankar G.R., and Robins R.K. J. Chem. Inf. Comput. Sci. 29 (1989) 163-172