Synthesis, antifungal activity and QSAR of some novel carboxylic acid amides

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Shijie DuZhaohai Qin

Abstract

A series of novel aromatic carboxylic acid amides were synthesized and tested for their activities against six phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to good activity. Among them N-(2-(1H-indazol-1-yl)phenyl)-2-(trifluoromethyl)benzamide (3c) exhibited the highest antifungal activity against Pythium aphanidermatum (EC50 = 16.75 µg/mL) and Rhizoctonia solani (EC50 = 19.19 µg/mL), compared to the reference compound boscalid with EC50 values of 10.68 and 14.47 µg/mL, respectively. Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were employed to develop a three-dimensional quantitative structure-activity relationship model for the activity of the compounds. In the molecular docking, a fluorine atom and the carbonyl oxygen atom of 3c formed hydrogen bonds toward the hydroxyl hydrogens of TYR58 and TRP173.

References

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Citations

Jan 14, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jin-Xia MuNa-Bo Sun
May 27, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Shijie DuZhaohai Qin
Jun 19, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yueting ZhouKe Sun
Jun 6, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xin-Yu HuoBin Dai
Mar 7, 2021·International Journal of Molecular Sciences·Sen YangCheng-Xia Tan

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Methods Mentioned

BETA
column chromatography

Software Mentioned

Linux
SYBYL
Tripos

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Antifungals (ASM)

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Antifungals

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.