Synthesis of pyrazole encompassing 2-pyridone derivatives as antibacterial agents

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 9, 2013, Pages 2714-2717

  Desai, Nisheeth C ^a   Rajpara, Kiran M ^a   Joshi, Vivek V ^a  

^a BHAVNAGAR UNIVERSITY   (India)

Author keywords

2 Pyridone; Antibacterial activity; Cytotoxicity; Pyrazole

Indexed keywords

2 PYRIDONE DERIVATIVE; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; 6 AMINO 1 [(1,3 DIPHENYL 1H PYRAZOLE 4 YL)METHYLENEAMINO] 4 (ARYL) 2 OXO 1,2 DIHYDROPYRIDINE 3,5 DICARBONITRILE; ANTIINFECTIVE AGENT; CIPROFLOXACIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BACTERIAL STRAIN; BROTH DILUTION; CARBON NUCLEAR MAGNETIC RESONANCE; CYTOTOXICITY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; HUMAN; HUMAN CELL; IN VITRO STUDY; INFRARED SPECTROMETRY; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PYOGENES;

ANIMALS; ANTI-BACTERIAL AGENTS; CELL SURVIVAL; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; HELA CELLS; HUMANS; MICE; MICROBIAL SENSITIVITY TESTS; NIH 3T3 CELLS; PYRAZOLES; PYRIDONES; STRUCTURE-ACTIVITY RELATIONSHIP;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; NEGIBACTERIA; POSIBACTERIA; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PYOGENES;

EID: 84876118274     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2013.02.077     Document Type: Article

References (31)

1. M. Grare, M. Mourer, S. Fontanay, J.B. Regnouf-de-Vains, C. Finance, and R.E. Duval J. Antimicrob. Chemother. 60 2007 575
2. W.-B. Choi, I.N. Houpis, H.R.O. Churchill, A. Molina, J.E. Lynch, R.P. Volante, P.J. Reider, and A.O. King Tetrahedron Lett. 36 1995 4571
3. M. Bhupathy, D.A. Conlon, K.M. Wells, J.R. Nelson, P.J. Reider, K. Rossen, J.W. Sager, R.P. Volante, B.D. Dorsey, J.M. Hoffman, S.A. Joseph, and S.L. McDaniel J. Heterocycl. Chem. 32 1995 1283
4. C.O. Kappe, and T. Kappe Monatsh. Chem. 120 1989 1095
5. A.Y. Saiki, L.L. Shen, C.M. Chen, J. Baranowski, and C.G. Lerner Antimicrob. Agents Chemother. 43 1999 1574
6. S. Brickner Chem. Ind. (London) 1997 131
7. M.E. Goldman, J.H. Nunberg, J.A. O'Brien, J.C. Quintero, W.A. Schleif, K.F. Freund, S.L. Gaul, W.S. Saari, J.S. Wai, and J.M. Hoffman Proc. Natl. Acad. Sci. U.S.A. 88 1991 6863
8. A.K. Gupta, and T. Plott Int. J. Dermatol. 43 2004 3
9. I. Collins, C. Moyes, W.B. Davey, M. Rowley, F.A. Bromidge, K. Quirk, J.R. Atack, R.M. McKernan, S.A. Thompson, K. Wafford, G.R. Dawson, A. Pike, B. Sohal, N.N. Tsou, R.G. Ball, and J.L. Castro J. Med. Chem. 2002 1887 45
10. M. Endoh, and M. Hori Expert Opin. Pharmacother. 7 2006 2179
11. N. Robert, C. Verrier, C. Hoarau, S. Celanire, and F. Marsais ARKIVOC 7 2008 92
12. E. Lo Presti, R. Boggia, A. Feltrin, G. Menozzi, P. Dorigo, and L. Mosti Farmaco 54 1999 465
13. Q. Li, L.A. Mitscher, and L.L. Shen Med. Res. Rev. 20 2000 231
14. T.J. Sullivan, J.J. Truglio, M.E. Boyne, P. Novichenok, X. Zhang, C.F. Stratton, H.-J. Li, T. Kaur, A. Amin, F. Johnson, R.A. Slayden, C. Kisker, and P.J. Tonge ACS Chem. Biol. 1 2006 43
15. A.M. Gilbert, A. Failli, J. Shumsky, Y. Yang, A. Severin, G. Singh, W. Hu, D. Keeney, P.J. Petersen, and A.H. Katz J. Med. Chem. 49 2006 6027
16. A.M. Isloor, B. Kalluraya, and P. Shetty Eur. J. Med. Chem. 44 2009 3784
17. I.V. Magedov, M. Manpadi, S.V. Slambrouck, W.F. Steelant, E. Rozhkova, N.M. Przheval'skii, S. Rogelj, and A. Kornienko J. Med. Chem. 50 2007 5183
18. G. Szabó, J. Fischer, Á. Kis-Varga, and K. Gyires J. Med. Chem. 51 2007 142
19. Y. Rajendra Prasad, A. Lakshmana Rao, L. Prasoona, K. Murali, and P. Ravi Kumar Bioorg. Med. Chem. Lett. 15 2005 5030
20. Z. Ozdemir, H.B. Kandilci, B. Gumusel, U. Calis, and A.A. Bilgin Eur. J. Med. Chem. 42 2007 373
21. A. Şener, M. Kasim Şener, I. Bildmci, R. Kasimogullari, and Y. Akçamur J. Heterocycl. Chem. 39 2002 869
22. G.A. Wachter, R.W. Hartmann, T. Sergejew, G.L. Grun, and D. Ledergerber J. Med. Chem. 39 1996 834
23. N.C. Desai, V.V. Joshi, K.M. Rajpara, H.V. Vaghani, and H.M. Satodiya J. Fluorine Chem. 142 2012 67
24. N.C. Desai, K.M. Rajpara, V.V. Joshi, H.V. Vaghani, and H.M. Satodiya Anti Infect. Agents 10 2012 75
25. N.C. Desai, K.M. Rajpara, V.V. Joshi, H.V. Vaghani, and H.M. Satodiya Med. Chem. Res. 22 2013 1172
26. O. Prakash, K. Pannu, R. Naithani, and H. Kaur Synth. Commun. 36 2006 3479
27. Synthesis of 2-cyano-N-((1,3-diphenyl-1H-pyrazol-4-yl)methylene) acetohydrazide (2): A mixture containing 1,3-diphenylpyrazole-4-carbaldehyde (1) (0.01 mol) and 2-cyanoacetohydrazide (0.01 mol) in 1,4-dioxane (30 mL) was refluxed for 1 h. After cooling, the crystals formed were filtered, washed with water and recrystallized from ethanol (95%) to give compound (2).
28. P.C. Hannan Vet. Res. 31 2000 373
29. P. Sharma, N. Rane, and V.K. Gurram Bioorg. Med. Chem. Lett. 14 2004 4185
30. D. Sharma, B. Narasimhan, P. Kumar, V. Judge, R. Narang, E. De Clercq, and J. Balzarini Eur. J. Med. Chem. 44 2009 2347
31. T. Mosmann J. Immunol. Methods 65 1983 55