Synthesis and structure-activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide derivatives as potential agents against A549 lung cancer cells

被引:164
作者
Xia, Yong
Dong, Zhi-Wu
Zhao, Bao-Xiang [1 ]
Ge, Xiao
Meng, Ning
Shin, Dong-Soo
Miao, Jun-Ying
机构
[1] Shandong Univ, Sch Chem & Chem Engn, Inst Organ Chem, Jinan 250100, Peoples R China
[2] Shandong Univ, Sch Life Sci, Inst Dev Biol, Jinan 250100, Peoples R China
[3] Changwon Natl Univ, Dept Chem, Chang Won 641773, South Korea
关键词
pyrazole carbohydrazide; A549; cells; apoptosis; structure-activity relationship; OXIDE INDUCES APOPTOSIS; PRELIMINARY BIOLOGICAL EVALUATION; GROWTH-INHIBITORY-ACTIVITY; SURVIVAL FACTORS; SAFROLE; ANTICANCER; DISCOVERY; DESIGN; 1-ETHOXY-3-(3,4-METHYLENEDIOXYPHENYL)-2-PROPANOL; INTEGRIN-BETA-4;
D O I
10.1016/j.bmc.2007.08.021
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of novel 1-arylmethyl-3-aryl- 1 H-pyrazole-5-carbohydrazide derivatives were synthesized, and the effects of all the compounds on A549 cell growth were investigated. The results showed that all the nine compounds had inhibitory effects on the growth of A549 cells and induced the cell apoptosis. The study on Structure-activity relationships and prediction of lipophilicities Of compounds showed that compounds with log P values in the range of 3.12-4.94 had more inhibitory effects oil the growth of A549 cells. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6893 / 6899
页数:7
相关论文
共 33 条
[1]   Novel anticancer drug discovery [J].
Buolamwini, JK .
CURRENT OPINION IN CHEMICAL BIOLOGY, 1999, 3 (04) :500-509
[2]   Synthesis and hypoglycemic evaluation of substituted pyrazole-4-carboxylic acids [J].
Cottineau, B ;
Toto, P ;
Marot, C ;
Pipaud, A ;
Chenault, J .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (16) :2105-2108
[3]  
DING XL, IN PRESS CHIN J ORG, V27
[4]   Safrole oxide induces apoptosis in A549 human lung cancer cells [J].
Du, AY ;
Zhang, SL ;
Miao, JY ;
Zhao, BX .
EXPERIMENTAL LUNG RESEARCH, 2004, 30 (06) :419-429
[5]   Safrole oxide induces apoptosis by up-regulating Fas and FasL instead of integrin β4 in A549 human lung cancer cells [J].
Du, AY ;
Zhao, BX ;
Miao, JY ;
Yin, DL ;
Zhang, SL .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (07) :2438-2445
[6]   Safrole oxide induces apoptosis by activating caspase-3,-8, and-9 in A549 human lung cancer cells [J].
Du, AY ;
Zhao, BX ;
Yin, DL ;
Zhang, SL ;
Miao, JY .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (01) :81-83
[7]   Discovery of a novel small molecule, 1-ethoxy-3-(3,4-methylenedioxyphenyl)-2-propanol, that induces apoptosis in A549 human lung cancer cells [J].
Du, AY ;
Zhao, BX ;
Yin, DL ;
Zhang, SL ;
Miao, JY .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (13) :4176-4183
[8]   N′,2-Diphenylquinoline-4-carbohydrazide based NK3 receptor antagonists [J].
Elliott, Jason M. ;
Carling, Robert W. ;
Chambers, Mark ;
Chicchi, Gary G. ;
Hutson, Peter H. ;
Jones, A. Brian ;
MacLeod, Angus ;
Marwood, Rose ;
Meneses-Lorente, Georgina ;
Mezzogori, Elena ;
Murray, Fraser ;
Rigby, Michael ;
Royo, Inmaculada ;
Russell, Michael G. N. ;
Sohal, Bindi ;
Tsao, Kwei Lan ;
Williams, Brian .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (22) :5748-5751
[9]   Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: Lead identification and SAR of 3-and 4-substituted derivatives [J].
Genin, MJ ;
Biles, C ;
Keiser, BJ ;
Poppe, SM ;
Swaney, SM ;
Tarpley, WG ;
Yagi, Y ;
Romero, DL .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (05) :1034-1040
[10]   Synthesis and antitumor activities of a series of novel quinoxalinhydrazides [J].
Grande, Fedora ;
Aiello, Francesca ;
De Grazia, Osvaldo ;
Brizzi, Antonella ;
Garofalo, Antonio ;
Neamati, Nouri .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (01) :288-294