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Synthesis, Antifungal Activity and 3D‐QSAR Study of Novel ( E )‐Longifolene‐Derived Tetralone Oxime Ethers
Author(s) -
Zhang Qianan,
Lin Guishan,
Duan Wengui,
Zhao Shuyan,
He Jiamin,
Lei Fuhou
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202100898
Subject(s) - chemistry , quantitative structure–activity relationship , gibberella zeae , antifungal , stereochemistry , chlorothalonil , tetralones , phthalide , tetralone , fungicide , carbon 13 nmr , biological activity , organic chemistry , fusarium , in vitro , biology , botany , biochemistry , microbiology and biotechnology
In search of novel antifungal agents from natural renewable biomass resources, twenty‐two ( E )‐longifolene‐derived tetralone oxime ether compounds were synthesized. Their structures were confirmed by IR, 1 H‐NMR, 13 C‐NMR, ESI‐MS and elemental analysis. The preliminary evaluation of in vitro antifungal activity showed that, at the concentration of 50 μg/mL, eight target compounds exhibited better antifungal activity than that of the positive control commercial fungicide chlorothalonil against Gibberella zeae , in which compound 5 a held excellent inhibition rate of 85.6 % against Fusarium oxysporum f. sp. Cucumerinu , and compound 5 d displayed a good and broad‐spectrum antifungal activity. Furthermore, a preliminary three‐dimensional quantitative structure‐activity relationship (3D‐QSAR) study was carried out by the CoMFA method for the inhibitory activity of the target compounds with aromatic R substituents against G. zeae , and a reasonable and effective 3D‐QSAR model ( r 2 =0.992, q 2 =0.523) was established.
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