Concise synthesis of dideoxy-epigallocatechin gallate (DO-EGCG) and evaluation of its anti-influenza virus activity.
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 anti-influenza virus activity.
Furuta
Takumi
T
Department of Synthetic Organic & Medicinal Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan. furuta@u-shizuoka-ken.ac.jp
Hirooka
Yasuo
Y
Abe
Ayako
A
Sugata
Yusuke
Y
Ueda
Mitsuru
M
Murakami
Kouki
K
Suzuki
Takashi
T
Tanaka
Kiyoshi
K
Kan
Toshiyuki
T
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002392:Catechin / Q000031:analogs & derivatives / Q000737:chemistry; D002478:Cells, Cultured; D004285:Dogs; D029521:Alphainfluenzavirus / Q000187:drug effects*
D000998:Antiviral Agents; C521563:dideoxy-epigallocatechin gallate; D002392:Catechin; C045651:epigallocatechin gallate