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Novel N ‐Cycloalkylcarbonyl‐ N ′‐arylthioureas: Synthesis, Design, Antifungal Activity and Gene Toxicity
Author(s) -
Kholodniak Olena V.,
Kazunin Maksym S.,
Meyer Fatuma,
Kovalenko Sergiy I.,
Steffens Karl G.
Publication year - 2020
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.202000212
Subject(s) - chemistry , antifungal , isothiocyanate , toxicity , antimicrobial , ames test , in vitro , elemental analysis , stereochemistry , salmonella , organic chemistry , biochemistry , microbiology and biotechnology , bacteria , biology , genetics
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 1 H‐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.