Concise synthesis of dideoxy-epigallocatechin gallate (DO-EGCG) and evaluation of its anti-influenza virus activity

被引：61
作者：
Furuta, Takumi
Hirooka, Yasuo
Abe, Ayako
Sugata, Yusuke
Ueda, Mitsuru
Murakami, Kouki
Suzuki, Takashi
Tanaka, Kiyoshi
Kan, Toshiyuki
机构：
[1] Univ Shizuoka, Dept Synthet Organ & Med Chem, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan
[2] Univ Shizuoka, Dept Biochem, Sch Pharmaceut Sci, CREST,JST,Suruga Ku, Shizuoka 4228526, Japan
[3] COE Program, Suruga Ku, Shizuoka 4228526, Japan
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2007年 / 17卷 / 11期
关键词：
epigallocatechin gallate; nitrochromene derivative; Nef reaction; anti-influenza virus activity;
D O I：
10.1016/j.bmcl.2007.03.041
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Dideoxy-epigallocatechin gallate (DO-EGCG) (2), a simplified analog of naturally occurring EGCG (1), was efficiently prepared by directly introducing a ketone group at C3 and successive reduction to the sec-alcohol with 2,3-cis stereochemistry. Compound 2 showed potent anti-influenza virus activity, indicating that the hydroxyl substituents on the A-ring are not crucial for antiinfluenza virus activity. (C) 2007 Elsevier Ltd. All rights reserved.
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收藏
页码：3095 / 3098
页数：4
相关论文
共 24 条
  • [1] Synthesis and antibacterial activity of hydrolytically stable (-)-epicatechin gallate analogues for the modulation of β-lactam resistance in Staphylococcus aureus
    Anderson, JC
    Headley, C
    Stapleton, PD
    Taylor, PW
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (10) : 2633 - 2635
  • [2] Asymmetric total synthesis of B-ring modified (-)-epicatechin gallate analogues and their modulation of β-lactam resistance in Staphylococcus aureus
    Anderson, JC
    Headley, C
    Stapleton, PD
    Taylor, PW
    [J]. TETRAHEDRON, 2005, 61 (32) : 7703 - 7711
  • [3] Identification and characterization of carbohydrate molecules in mammalian cells recognized by dengue virus type 2
    Aoki, C
    Hidari, KIPJ
    Itonori, S
    Yamada, A
    Takahashi, N
    Kasama, T
    Hasebe, F
    Islam, MA
    Hatano, K
    Matsuoka, K
    Taki, T
    Guo, CT
    Takahashi, T
    Sakano, Y
    Suzuki, T
    Miyamoto, D
    Sugita, M
    Terunuma, D
    Morita, K
    Suzuki, Y
    [J]. JOURNAL OF BIOCHEMISTRY, 2006, 139 (03) : 607 - 614
  • [4] Nitroalkanes and ethyl glyoxalate as common precursors for the preparation of both β-keto esters and α,β-unsaturated esters
    Ballini, R
    Fiorini, D
    Palmieri, A
    [J]. TETRAHEDRON LETTERS, 2004, 45 (38) : 7027 - 7029
  • [5] Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction)
    Ballini, R
    Petrini, M
    [J]. TETRAHEDRON, 2004, 60 (05) : 1017 - 1047
  • [6] Green tea: Health benefits as cancer preventive for humans
    Fujiki, H
    [J]. CHEMICAL RECORD, 2005, 5 (03) : 119 - 132
  • [7] Solid-phase synthesis of photoaffinity probes: highly efficient incorporation of biotin-tag and cross-linking groups
    Kan, T
    Tominari, Y
    Morohashi, Y
    Natsugari, H
    Tomita, T
    Iwatsubo, T
    Fukuyama, T
    [J]. CHEMICAL COMMUNICATIONS, 2003, (17) : 2244 - 2245
  • [8] Katoh T, 1999, HETEROCYCLES, V50, P833
  • [9] An efficient synthesis of (±)-epigallocatechin gallate by reductive intramolecular etherification
    Kitade, Makoto
    Ohno, Yoshiaki
    Tanaka, Hiroshi
    Takahashi, Takashi
    [J]. SYNLETT, 2006, (17) : 2827 - 2829
  • [10] Enantioselective synthesis of epigallocatechin-3-gallate (EGCG), the active polyphenol component from green tea
    Li, LH
    Chan, TH
    [J]. ORGANIC LETTERS, 2001, 3 (05) : 739 - 741
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