Synthesis and antimicrobial activities of novel 1,5-diaryl pyrazoles

European Journal of Medicinal Chemistry

Volumn 45, Issue 3, 2010, Pages 1173-1180

  Ragavan, R Venkat ^a,b   Vijayakumar, V ^a   Kumari, N Suchetha ^c  

^a VIT UNIVERSITY   (India)

^b SYNGENE INTERNATIONAL LTD   (India)

^c NITTE DEEMED TO BE UNIVERSITY   (India)

Author keywords

1,5 Diaryl pyrazoles; 2 (5 (4 Chlorophenyl) 1 (4 fluorophenyl) 1H pyrazole 3 yl)thiazoles; 4 Piperidine amide pharmacophore; 5 (4 Chlorophenyl) 1 (4 fluorophenyl) 1H pyrazole 3 carboxamides; Antibacterial activity; Antifungal activity; Synthesis

Indexed keywords

1 [4 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOLE 3 CARBONYL]PIPERAZIN 1 YL]HEXAN 1 ONE; 1 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOLE 3 CARBONYL]PIPERAZINE 1 CARBOXYLIC ACID TERT BUTYL ESTER; 1 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL)1H PYRAZOLE 3 CARBONYL]PIPERIDINE 4 YL ESTER; 2 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOL 3 YL] 4 METHYL THIAZOLE 5 CARBOXYLIC ACID HYDRAZIDE; 2 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOL 3 YL] 4 METHYLTHIAZOLE 5 CARBOXYLIC ACID ETHYL ESTER; 2 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOLE 3 CARBOXAMIDO] 4 METHYLTHIAZOLE 5 CARBOXYLIC ACID; 4 (4 CHLOROPHENYL) 2 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOL 3 YL]THIAZOLE; 4 [2 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOLE 3 YL]THIAZOL 4 YL]BENZONITRILE; 4 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOLE 3 CARBONYL]PIPERAZINE 1 CARBOXYLIC ACID ALLYLAMIDE; 4 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOLE 3 CARBONYL]PIPERAZINE 1 CARBOXYLIC ACID ETHYLAMIDE; 4 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOLE 3 CARBONYL]PIPERAZINE 1 CARBOXYLIC ACID TERT BUTYL ESTER; 4 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOLE 3 CARBONYL]PIPERAZINE 1 CARBOXYLIC ACID(4 CYANOPHENYL)AMIDE; 5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOLE 3 CARBOXYLIC ACID; 5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOLE 3 YL (4 CYCLOPROPANECARBONYLPIPERAZIN 1 YL)METHANONE; 5 (4 CHLOROPHENYL) N (6 CHLOROPYRIDIN 3 YL) 1 (4 FLUOROPHENYL) 1H PYRAZOLE 3 CARBOXAMIDE; 5 [2 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOL 3 YL] 4 METHYL THIAZOL 5 YL] 3H [1,3,4]OXADIAZOLE 2 ONE; [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOL 3 YL] (4 HYDROXY PIPERIDIN 1 YL)METHANONE; [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOL 3 YL] (4 PROP 2YNYL PIPERAZIN 1 YL)METHANONE; [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOLE 3 CARBONYL]PIPERAZIN 1 YL METHANONE; ANTIINFECTIVE AGENT; CICLOPIROXOLAMINE; CIPROFLOXACIN; ETHYL 2 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOLE 3 CARBOXAMIDO] 4 METHYLTHIAZOLE 5 CARBOXYLATE; N [N' [2 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOL 3 YL] 4 METHYL THIAZOLE 5 CARBONYL]HYDRAZINOCARBOTHIONYL] 4 TRIFLUOROMETHYL BENZAMIDE; N [N' [2 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOL 3 YL] 4 METHYL THIAZOLE 5 CARBONYL]HYDRAZINOCARBOTHIONYL]ALLYLAMIDE; N [N' [2 [5 (4 CHLOROPHENYL) 1 (4 FLUOROPHENYL) 1H PYRAZOL 3 YL] 4 METHYLTHIAZOLE 5 CARBONYL]HYDRAZINOCARBOTHIONYL]BENZAMIDE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FLAVUS; ASPERGILLUS FUMIGATUS; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; INFRARED SPECTROSCOPY; KLEBSIELLA PNEUMONIAE; MASS SPECTROMETRY; NONHUMAN; PENICILLIUM MARNEFFEI; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; TRICHOPHYTON MENTAGROPHYTES;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; BACTERIA; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FUNGI; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PYRAZOLES;

EID: 75849162554     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.12.042     Document Type: Article

References (42)

1. Menozzi G., Mosti L., Bruno O., Lo Presti E., Musiu C., Longu S., La Colla P., Filippelli W., Falcone G., and Piucci B. Farmaco 54 (1999) 416-422
2. Menozzi G., Merello L., Fossa P., Schenone S., Ranise A., Mosti L., Bondavalli F., Loddo R., Murgioni C., Mascia V., La Colla P., and Tamburini E. Bioorg. Med. Chem. 12 (2004) 5465-5483
3. Bekhit A.A., Fahmy H.T.Y., Rostom S.A.F., and Baraka A.M. Eur. J. Med. Chem. 38 (2003) 27-36
4. Tandon V.K., Yadav D.B., Chaturvedi A.K., and Shukla P.K. Bioorg. Med. Chem. Lett. 15 (2005) 3288-3291
5. Akbas E., and Berber I. Eur. J. Med. Chem. 40 (2005) 401-405
6. Cernuchova P., Vo-Thanh G., Milata V., Loupy A., Jantova' S., and Theiszova M. Tetrahedron 61 (2005) 5379-5387
7. Lambris J.D., and Muller-Eberhard H. J. Mol. Immunol. 23 (1986) 1237-1242
8. Nguyet T.H.D., Cristina M.S., Sylvie D., Marie-Agnes S., Patrick M.D., and Daniel M. Arch. Biochem. Biophys. 394 (2001) 189-200
9. Aiello E., Aiello S., Mingoia F., Bacchi A., Pelizzi G., Musiu C., Setzu M.G., Pani A., La Colla P., and Marongiu M.E. Bioorg. Med. Chem. 8 (2000) 2719-2728
10. Kaymakcioglu B.K., and Rollas II S. Farmaco 57 (2002) 595-599
11. Dardari Z., Boudouma M., Sebban A., Bahloul A., Kitane S., and Berrada II M. Farmaco 59 (2004) 673-678
12. Tanitame A., Oyamada Y., Ofuji K., Terauchi H., Kawasaki M., Wachi M., and Yamagishi J. Bioorg. Med. Chem. Lett. 15 (2005) 4299-4303
13. Aggarwal R., Kumar V., Tyagi P., and Singh S.P. Bioorg. Med. Chem. 14 (2006) 1785-1791
14. Ismail Z.H., Gawad S.M.A., Aziem A.A., and Ghorab M.M. Phosphours Sulfur Silicon Relat. Elem. 178 (2003) 1795-1805
15. Kane Jr. J.L., Hirth B.H., Liang B., Gourlie B.B., Nahill S., and Barsomian G. Bioorg. Med. Chem. Lett. 13 (2003) 4463-4466
16. Kumar V., Aggarwal R., Tyagi P., and Singh S.P. Eur. J. Med. Chem. 40 (2005) 922-927
17. Kucukguzel S.G., Rollas S., Erdeniz H., Kiraz M., Ekinci A.C., and Vidin A. Eur. J. Med. Chem. 3 (2000) 761-771
18. Mashevskaya V., Kol'tsova S.V., Voronina E.V., Odegova T.F., and Maslivets A.N. Pharm. Chem. J. 35 (2001) 18-21
19. Krivonogov V.P., Tolstikov G.A., Lazareva D.N., Davydova V.A., Zarudii F.S., Krivonogova I.I., and Murinov Yu.I. Pharm. Chem. J. 35 (2001) 26-29
20. Tanitame A., Oyamada Y., Ofuji K., Fujimoto M., Suzuki K., Ueda T., Terauchi H., Kawasaki M., Nagai K., Wachi M., and Yamagishi J. J. Bioorg. Med. Chem. 12 (2004) 5515-5524
21. Bekhit A.A., Ashour H.M.A., Ghany Y.S.A., Bekhit A.E.A., and Baraka A. Eur. J. Med. Chem. 43 (2008) 456-463
22. Singh S.P., Prakash O., Tomer R.K., and Sawhney S.N. Indian J. Chem. 16B (1978) 733
23. Tewari A.K., and Mishra A. Bioorg. Med. Chem. 9 (2001) 715-718
24. Prakash O., Kumar R., and Parkash V. Eur. J. Med. Chem. 43 (2008) 435-440
25. Kudo N., Furuta S., Taniguchi M., Endo T., and Sato K. Chem. Pharm. Bull. 47 (1999) 857-868
26. Jung J.C., Watkins E.B., and Avery M.A. Tetrahedron 58 (2002) 3639-3646
27. Vera-DiVaio M.A.F., Freitas A.C.C., Castro H.C.A., de Albuquerque S., Cabral L.M., Rodrigues C.R., Albuquerque M.G., Martins R.C.A., Henriques M.G., and Dias L.R.S. Bioorg. Med. Chem. 17 (2009) 295-302
28. Skipper H.E., Robins R.K., and Thompson J.R. Proc. Soc. Exp. Bio. Med. 89 (1955) 589-594
29. Hsu T.C., Robins R.K., and Cheng C.C. Science 13 (1956) 848-868
30. Storer R., Ashton C.J., Baxter A.D., Hann M.M., Marr C.L.P., Mason A.M., Mo C.L., Myers P.L., Noble S.A., Penn C.R., Weir N.G., Woods J.M., and Coe P.L. Nucleosides Nucleotides Nucleic Acids 18 (1999) 203-216
31. Genin M.J., Biles C., Keiser B.J., Poppe S.M., Swaney S.M., Tarpley W.G., Yagi Y., and Romero D.L. J. Med. Chem. 43 (2000) 1034-1040
32. J.X. Qiao, D.J. Pinto, M.J. Orwat, W. Han, S.R. Friedrich, PCT Int. Appl. WO 03 99, 276 (Chem. Abstr., 2004, 140, 16722g).
33. Baraldi P.G., Bovero A., Fruttarolo F., Romagnoli R., Tabrizi M.A., Preti D., Varani K., Borea P.A., and Moorman A.R. Bioorg. Med. Chem. 11 (2003) 4161-4169
34. A.W. Stamford, Y. Wu, PCT Int. Appl. WO 2004, 5262 (Chem. Abstr. 2004, 140, 11141p).
35. M.L. Brown, M. Cheung, S.H. Dickerson, D.H. Drewy, K.E. Lackey, A.J. Peat, S.A. Thomson, J.M. Veal, J.L.R. Wilson, PCT Int. Appl. WO 2004, 9596 (Chem. Abstr. 2004, 140, 128436y).
36. D.A. Heerding, PCT Int. Appl. WO 03 103686 (Chem. Abstr. 2004,140, 42170v).
37. Duma J., Hatoum-Mokdad H., Sibley R., Riedl B., Scott W.J., Monahan M.K., Lowinger T.B., Brennan C., Natero R., Turner T., Johnson J.S., Schoenlebar R., Bhargava A., Wilhelm S.M., Housley T.J., Ranges G.E., and Shrikhande A. Bioorg. Med. Chem. Lett. 10 (2000) 2051-2054
38. Venkat Ragavan R., Vijayakumar V., and Suchetha Kumari N. Eur. J. Med. Chem. 44 (2009) 3852-3857
39. Koragiri V.K., Suthrapu S., Reddy J.M., Rao C.P., Bollugoddu V., Bhattacharya A., and Bandichhor R. Org. Pro. Res. Develop. 11 (2007) 910-912
40. Cruickshank R., Duguid J.P., Marmion B.P., and Swain R.H.A. Medicinal Microbiology. twelfth ed. vol. 2 (1975), Churchill Livingstone, London p. 196
41. Collins A.H. Microbiological Methods. second ed. (1976), Butterworth, London
42. Skaggs B.A.A., Motley M., Warnock D.W., and Morrison C.J. J. Clin. Microbiol. 38 (2000) 2254-2260