Novel Daidzein Analogs and Their in Vitro Anti‐Influenza Activities. Issue 4 (April 2015)

• Record Type: Journal Article
• Authors: Chung, Shu‐Ting; Huang, Yi‐Ting; Hsiung, Hsin‐Yi; Huang, Wen‐Hsin; Yao, Chen‐Wen; Lee, An‐Rong
• Is Part Of: Chemistry & biodiversity. Volume 12:Issue 4(2015:Apr.)
• Page Start: 685
• Page End: 696
• Publication Date: 2015-04
• Subjects: Biochemistry -- Periodicals; Molecular biology -- Periodicals; Biodiversity -- Periodicals; 572
• DOI: 10.1002/cbdv.201400337
• Languages: English
• ISSNs: 1612-1872

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A series of novel isoflavonoids were synthesized based on structural modifications of daidzein, an active ingredient of traditional Chinese medicine (TCM) and evaluated for their anti‐influenza activity, <italic>in vitro</italic>, against H1N1 <italic>Tamiflu</italic>‐resistant (H1N1 TR) virus in the MDCK cell line. Among them, 4‐oxo‐4<italic>H</italic>‐1‐benzopyran‐8‐carbaldehydes <bold>11a</bold>–<bold>11g</bold> were most promising, and they demonstrated better activities and selectivities comparable to those the reference ribarivin, a nucleoside antiviral agent. 3‐(4‐Bromophenyl)‐7‐hydroxy‐4‐oxo‐4<italic>H</italic>‐1‐benzopyran‐8‐carboxaldehyde (<bold>11c</bold>) displayed the best inhibitory activity (<italic>EC</italic>₅₀, 29.0 μ<sc>M</sc>) and selectivity index (<italic>SI</italic>&gt;10.3). Analysis of the structureactivity relationships (SAR) indicated that both the non‐naturally‐occurring Br‐substituted <italic>B</italic>‐ring and appropriate CHO and OH groups on the <italic>A</italic>‐ring might be critical for the activity and selectivity against H1N1 TR influenza viruses.</p> </abstract>