Novel N‐cycloalkylcarbonyl‐N′‐aryl‐thioureas: Synthesis, Design, Antifungal Activity and Gene Toxicity,Chemistry & Biodiversity

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Novel N‐cycloalkylcarbonyl‐N′‐aryl‐thioureas: Synthesis, Design, Antifungal Activity and Gene Toxicity
Chemistry & Biodiversity ( IF 2.3 ) Pub Date : 2020-06-23 , DOI: 10.1002/cbdv.202000212
Olena V Kholodniak _{1,

2} , Maksym S Kazunin ₁ , Fatuma Meyer ₂ , Sergiy I Kovalenko ₁ , Karl G Steffens ₂

Affiliation

A synthesis method of novel N‐cycloalkylcarbonyl‐N′‐arylthioureas was developed. It consists of sequential addition of equimolecular amounts of ammonium isothiocyanate and substituted anilines to cycloalkylcarbonyl chlorides. The identity and purity of products were confirmed by LC/MS spectra, their structure by elemental analysis, IR and 1H‐NMR spectra. Preliminary antimicrobial screening for standard microorganisms and molecular docking allowed to select several structures for antifungal and genetic toxicity studies. Conducted in vitro screening of 9 compounds for antifungal potential against 11 phytopathogenic fungi and three Phytophthora strains revealed that two N‐(arylcarbamothioyl) cyclopropanecarboxamides at a concentration of 50 μg/ml exhibited activities comparable to the standard antifungal agent ‘Cyproconazole’. Analysis of mutagenicity of novel thioureas using the Salmonella reverse mutagenicity assay (‘Ames Test’) showed a low gene‐toxicity profile.

中文翻译：

新型 N-环烷基羰基-N'-芳基-硫脲：合成、设计、抗真菌活性和基因毒性

开发了一种新型N-环烷基羰基-N'-芳基硫脲的合成方法。它包括将等分子量的异硫氰酸铵和取代的苯胺依次添加到环烷基羰基氯中。产品的特性和纯度通过 LC/MS 光谱确认，其结构通过元素分析、IR 和 1H-NMR 光谱确认。标准微生物的初步抗菌筛选和分子对接允许选择几种结构进行抗真菌和遗传毒性研究。对 9 种化合物对 11 种植物病原真菌和三种疫霉属菌株的抗真菌潜力进行了体外筛选，结果表明，浓度为 50 μg/ml 的两种 N-（芳基氨基甲硫酰）环丙烷甲酰胺表现出与标准抗真菌剂“环丙康唑”相当的活性。

更新日期：2020-06-23

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