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Design, Synthesis and Biological Evaluation of Novel N‐(4‐([2,2′:5′,2′′‐Terthiophen]‐5‐yl)‐2‐methylbut‐3‐yn‐2‐yl) Benzamide Derivatives
Author(s) -
Zhu Youquan,
Zhang Haili,
Wang Danyang,
Li Lei,
Xu Han,
Li Huabin,
Ma Yuan
Publication year - 2015
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201400654
Subject(s) - benzamide , chemistry , tobacco mosaic virus , substituent , bioassay , van der waals force , stereochemistry , virus , combinatorial chemistry , organic chemistry , molecule , virology , genetics , biology
On the basis of the principle of combination of active groups, a series of novel N ‐(4‐([2,2′:5′,2′′‐terthiophen]‐5‐yl)‐2‐methylbut‐3‐yn‐2‐yl) benzamide derivatives were designed, synthesized and systematically evaluated for their antiviral activity against tobacco mosaic virus (TMV). The bioassay results showed that most of these compounds displayed good anti‐TMV activity, and some of them exhibited higher antiviral activity than commercial Ningnanmycin. Especially, compound 8e with excellent anti‐TMV activity (inactivation activity, 92.3%/500 µg·mL −1 ; curative activity, 85.7%/500 µg·mL −1 and protection activity, 64.7%/500 µg·mL −1 ) emerged as a potential inhibitor of plant virus TMV. Quantitative structure‐activity relationship studies proved that the van der Waals volume ( V ) and electronic parameter (∑(∑ σ o + σ p ) and ∑ σ m ) for the substituent R 1 were very important for antiviral activities in this class of compounds.