Synthesis and antibacterial activities of N-[(1-aryl-3-phenyl-pyrazol-4-yl)methylene]-2-(halo-o-hydroxyphenyl)hydrazide derivatives

Ya Liu , Bo-wei Lu , Jun-rui Lu , Chun-wei Xin , Jian-fa Li , Jiang-bei Mu , Xiu-rong Bao

Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (3) : 449 -453.

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Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (3) : 449 -453. DOI: 10.1007/s40242-013-2491-2
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Synthesis and antibacterial activities of N-[(1-aryl-3-phenyl-pyrazol-4-yl)methylene]-2-(halo-o-hydroxyphenyl)hydrazide derivatives

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Abstract

A series of novel N-[(1-aryl-3-phenyl-pyrazol-4-yl)methylene]-2-(halo-o-hydroxyphenyl)hydrazide derivatives was synthesized and the antibacterial activity of each of them was evaluated. The supposed reaction mechanism of acquiring compounds 3a–3d is that catalytic activity is enhanced by the electron-donating groups of the first phenyl ring while decreased by electron-withdrawing groups of that ring. The result of preliminary bioassay shows that the lowest minimal inhibitory concentration(MIC) of the title compounds against Escherichia coli is 2 μg/mL. MIC values against Monilia albican and Staphlococcus aureus are as low as 4 μg/mL. They will be a series of potential antibacterial compounds against fungi and gram-negative bacteria.

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N-[(1-Aryl-3-phenyl-pyrazol-4-yl)methylene]-2-(halo-o-hydroxyphenyl)hydrazide / Structure-activity relationship / Antibacterial activity

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Ya Liu, Bo-wei Lu, Jun-rui Lu, Chun-wei Xin, Jian-fa Li, Jiang-bei Mu, Xiu-rong Bao. Synthesis and antibacterial activities of N-[(1-aryl-3-phenyl-pyrazol-4-yl)methylene]-2-(halo-o-hydroxyphenyl)hydrazide derivatives. Chemical Research in Chinese Universities, 2013, 29(3): 449-453 DOI:10.1007/s40242-013-2491-2

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References

[1]

Sridhar R, Perumal P T, Etti S, Shanmugam G, Ponnuswamy M N, Prabavathy V R, Mathivanan N. Bioorg. Med. Chem. Lett., 2004, 14: 6035.

[2]

Richard J H, Rubin J R, Debra R H, Erli Z, Mark E S. J. Biol. Chem., 1999, 274(16): 11110.

[3]

Sivaraman S, Sullivan T J, Johnson F, Novichenok P. J. Med. Chem., 2004, 47(3): 509.

[4]

Lu J R, Ma X M, Liu M, Yin N, Chen L R, Bao X R. Chem. J. Chinese Universities, 2007, 28(11): 2081.

[5]

Ismail M A, Nabil A E M, Abouzid K A. Bioorg. Med. Chem., 2009, 17(10): 3739.

[6]

Tanitame A, Oyamada Y, Ofuji K, Fujimoto M, Iwai N, Hiyama Y, Suzuki K, Ito H, Terauchi H, Kawasaki M, Nagai K, Wachi M, Yamagishi J. J. Med. Chem., 2004, 47(14): 3693.

[7]

Genin M J, Biles C, Keiser B J, Swaney S M, Tarpley W G, Yagi Y, Romero D L. J. Med. Chem., 2000, 43(5): 1034.

[8]

Xia Y, Fan C D, Zhao B X, Zhao J, Shin D S, Miao J Y. Eur. J. Med. Chem., 2008, 43(11): 2347.

[9]

Xia Y, Dong Z W, Zhao B X, Ge X, Meng N, Shin D S, Miao J Y. Bioorg. Med. Chem., 2007, 15(22): 6893.

[10]

Dalla V L, Marini A M, Salerno S, LaMotta C, Condello M, Arancia G, Agostinelli E, Toninello A. Bioorg. Med. Chem., 2009, 17(1): 326.

[11]

Gaber H M, Bagley M C, Sherif S M, Abdul U M. J. Hetero. Chem., 2010, 47: 1162.

[12]

Li X L, Lin Y J, Wang Q Q, Yuan Y K, Zhang H, Qian X H. Eur. J. Med. Chem., 2011, 46: 1274.

[13]

Akbas E, Berber I, Sener A, Hasanov B. Il Farmaco, 2005, 60(1): 23.

[14]

Prakash O., Kumar R., Parkash V. Eur. J. Med. Chem., 2008, 43: 435.

[15]

Helmerhost E J, Breeuwer P, Hof W V, Walgreen E, Oomen L C, Veerman E C I, Amerongen A V N, Abee T. J. Biol. Chem., 1999, 274(11): 7286.

[16]

Ji H T, Zhang W N, Zhou Y J, Zhang M, Zhu J, Song Y L, Lu J, Zhu J. J. Med. Chem., 2000, 43(13): 2493.

[17]

Han R, Zhang J H, Li S X, Cao S F, Geng H. J. Med. Chem., 2010, 58(24): 12810.

[18]

Zou M, Lu J R, Xin C W, Lu B W, Zhu S S, Liu Q, Li J Y, Qiu J B, Bao X R. Chem. J. Chinese Universities, 2010, 31(8): 1590.

[19]

Zhao X, Lu J R, Xin C W, Lu B W, Bao X R, Li J F, Liu Y, Yang X Y, Yuan Y. Chem. Res. Chinese Universities, 2012, 28(3): 424.

[20]

Shi X F, Zhan J R, Liao B R. Intermed. Chem., 2010, 40(5): 47.

[21]

Zhang M, Lu J R, Xin C W, Liu F, Wang Q Q, Li H J, Wei R B, Bao X R. Chin. J. Org. Chem., 2009, 29(10): 1645.

[22]

Sahar M I B, Rasha M B. Bioorg. Med. Chem., 2011, 19: 4506.

[23]

Yoshikazu A, Ichiro A, Kazuhiko I, Fujio I, Masaki H, Takayoshi I. J. Med. Chem., 2005, 48(9): 3443.

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