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Synthesis of 2‐Aryl‐ and 2‐Haloarylbenzimidazole‐ N 1‐acetamido Conjugates and a Preliminary Evaluation of Their Antifungal Properties
Author(s) -
AbdelWahab Sherief M.,
Abdelsamii Zakaria K.,
AbdelFattah Hanan A.,
ElEtrawy Abdallah S.,
Dawe Louise N.,
Swaroop Toreshettahally R.,
Georghiou Paris E.
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801151
Subject(s) - moiety , aryl , fluconazole , chemistry , amphotericin b , aspergillus fumigatus , stereochemistry , conjugate , candida albicans , antifungal , agarose , minimum inhibitory concentration , combinatorial chemistry , in vitro , organic chemistry , chromatography , biochemistry , microbiology and biotechnology , biology , mathematical analysis , alkyl , mathematics
A series of new 2‐arylbenzimidazole‐ N ‐1 acetamido conjugates have been synthesized and characterized. Their antifungal activities were evaluated against fluconazole‐resistant C. albicans and A. fumigatus by the inhibition zone technique and were compared with the standard amphotericin B. Minimum inhibitory concentrations were determined for the most potent compounds, after preliminary structure‐activity analysis. Based upon these results a sub‐set of twelve ethylglycinyl ester conjugates bearing fluoro, chloro or bromo substituents on the 2‐phenyl moiety were examined for structure‐activity relationships using an agarose diffusion method employing a hypersensitive Sacharomyces cerevisiae strain. None of these compounds however showed significant activity at the concentrations tested. Single‐crystal X‐ray determinations were conducted on two of the newly synthesized compounds and were compared with DFT computational analysis.