Synthesis of O-prenylated and O-geranylated derivatives of 5-benzylidene2,4-thiazolidinediones and evaluation of their free radical scavenging activity as well as effect on some phase II antioxidant/detoxifying enzymes

被引:51
作者
Hossain, Sk. Ugir [1 ]
Bhattacharya, Sudin [1 ]
机构
[1] Chittaranjan Natl Canc Inst, Dept Canc Chemoprevent, Kolkata 700026, W Bengal, India
关键词
2,4-thiazolidinediones; radical scavenger; detoxifying enzyme; mice;
D O I
10.1016/j.bmcl.2006.12.040
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of 5-arylidene-2,4-thiazolidinediones and its geranyloxy or prenyloxy derivative were synthesized and studied for their radical scavenging activity using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Their comparable scavenging activities were expressed as IC50 value. Compounds 2c, 2d, 4d, and 6a showed appreciable radical scavenging activities. The vanillin based thiazolidinedione compound 2c displayed highest activity comparable to that of alpha-tocopherol. But in vivo, compound 6a showed better results in inducing phase II detoxifying/antioxidative enzyme. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1149 / 1154
页数:6
相关论文
共 30 条
[21]   ANTIOXIDATIVE PROPERTIES OF XANTHAN ON THE AUTOXIDATION OF SOYBEAN OIL IN CYCLODEXTRIN EMULSION [J].
SHIMADA, K ;
FUJIKAWA, K ;
YAHARA, K ;
NAKAMURA, T .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1992, 40 (06) :945-948
[22]  
SHOFF SM, 1991, CANCER RES, V51, P37
[23]   ON THE NATURE OF SELENIUM TOXICITY AND CARCINOSTATIC ACTIVITY [J].
SPALLHOLZ, JE .
FREE RADICAL BIOLOGY AND MEDICINE, 1994, 17 (01) :45-64
[24]  
Tanaka-Kagawa T, 1998, J PHARMACOL EXP THER, V285, P335
[25]   Volatile isoprenoid constituents of fruits, vegetables and herbs cumulatively suppress the proliferation of murine B16 melanoma and human HL-60 leukemia cells [J].
Tatman, D ;
Mo, HB .
CANCER LETTERS, 2002, 175 (02) :129-139
[26]   DPPH radical-scavenging effect of several phenylpropanoid compounds and their glycoside derivatives [J].
Tominaga, H ;
Kobayashi, Y ;
Goto, T ;
Kasemura, K ;
Nomura, M .
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2005, 125 (04) :371-375
[27]   OXAZOLE, THIAZOLE, AND IMIDAZOLE DERIVATIVES OF 2,6-DI-TERT-BUTYLPHENOL AS DUAL 5-LIPOXYGENASE AND CYCLOOXYGENASE INHIBITORS [J].
UNANGST, PC ;
CONNOR, DT ;
CETENKO, WA ;
SORENSON, RJ ;
SIRCAR, JC ;
WRIGHT, CD ;
SCHRIER, DJ ;
DYER, RD .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (08) :1729-1734
[28]   Efficacy of potential chemopreventive agents on rat colon aberrant crypt formation and progression [J].
Wargovich, MJ ;
Jimenez, A ;
McKee, K ;
Steele, VE ;
Velasco, M ;
Woods, J ;
Price, R ;
Gray, K ;
Kelloff, GJ .
CARCINOGENESIS, 2000, 21 (06) :1149-1155
[29]  
YU SG, 1995, J NUTR, V125, P2763
[30]   EFFICACY OF BETA-IONONE IN THE CHEMOPREVENTION OF RAT MAMMARY CARCINOGENESIS [J].
YU, SG ;
ANDERSON, PJ ;
ELSON, CE .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1995, 43 (08) :2144-2147