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
  • [1] Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones
    Bruno, G
    Costantino, L
    Curinga, C
    Maccari, R
    Monforte, F
    Nicolò, F
    Ottanà, R
    Vigorita, MG
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (04) : 1077 - 1084
  • [2] Burke YD, 2002, ANTICANCER RES, V22, P3127
  • [3] Inhibition of pancreatic cancer growth by the dietary isoprenoids farnesol and geraniol
    Burke, YD
    Stark, MJ
    Roach, SL
    Sen, SE
    Crowell, PL
    [J]. LIPIDS, 1997, 32 (02) : 151 - 156
  • [4] Ligands for peroxisome proliferator-activated receptorγ and retinoic acid receptor inhibit growth and induce apoptosis of human breast cancer cells in vitro and in BNX mice
    Elstner, E
    Müller, C
    Koshizuka, K
    Williamson, EA
    Park, D
    Asou, H
    Shintaku, P
    Said, JW
    Heber, D
    Koeffler, HP
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (15) : 8806 - 8811
  • [5] Regiospecific reduction of 5-benzylidene-2,4-thiazolidinediones and 4-oxo-2-thiazolidinethiones using lithium borohydride in pyridine and tetrahydrofuran
    Giles, RG
    Lewis, NJ
    Quick, JK
    Sasse, MJ
    Urquhart, MWJ
    Youssef, L
    [J]. TETRAHEDRON, 2000, 56 (26) : 4531 - 4537
  • [6] A ferulic acid derivative, ethyl 3-(4′-geranyloxy-3-methoxyphenyl)-2-propenoate, as a new candidate chemopreventive agent for colon carcinogenesis in the rat
    Han, BS
    Park, CB
    Takasuka, N
    Naito, A
    Sekine, K
    Nomura, E
    Taniguchi, H
    Tsuno, T
    Tsuda, H
    [J]. JAPANESE JOURNAL OF CANCER RESEARCH, 2001, 92 (04): : 404 - 409
  • [7] Isoprenoids suppress the growth of murine B16 melanomas in vitro and in vivo
    He, L
    Mo, HB
    Hadisusilo, S
    Qureshi, AA
    Elson, CE
    [J]. JOURNAL OF NUTRITION, 1997, 127 (05) : 668 - 674
  • [8] Inhibitory effects of multi-substituted benzylidenethiazolidine-2,4-diones on LDL oxidation
    Jeong, TS
    Kim, JR
    Kim, KS
    Cho, KH
    Bae, KH
    Lee, WS
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (15) : 4017 - 4023
  • [9] PPAR-γ agonists inhibit production of monocyte inflammatory cytokines
    Jiang, CY
    Ting, AT
    Seed, B
    [J]. NATURE, 1998, 391 (6662) : 82 - 86
  • [10] Kubota T, 1998, CANCER RES, V58, P3344