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Molecules 2018, 23(4), 831; https://doi.org/10.3390/molecules23040831

Synthesis and Anticandidal Activity of New Imidazole-Chalcones

1
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu Universty, 26470 Eskişehir, Turkey
2
Doping and Narcotic Compounds Analysis Laboratory, Faculty of Pharmacy, Anadolu Universty, 26470 Eskişehir, Turkey
3
Department of Pharmaceutical Toxicology, Faculty of Pharmacy, Anadolu Universty, 26470 Eskişehir, Turkey
*
Author to whom correspondence should be addressed.
Received: 23 March 2018 / Revised: 28 March 2018 / Accepted: 29 March 2018 / Published: 4 April 2018
(This article belongs to the Special Issue Chalcone: A Privileged Structure in Medicinal Chemistry)
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Abstract

In the present work, 15 new 1-(4-(1H-imidazol-1-yl)phenyl)-3-(4-substituedphenyl)prop-2-en-1-one derivatives (3a3o) were synthesized to evaluate their antifungal activity. Structures of newly synthesized imidazole derivatives (3a3o) were characterized by IR, 1H-NMR, 13C-NMR, and LCMSMS spectroscopic methods. The anticandidal activity of compounds (3a3o) against C. albicans (ATCC 24433), C. krusei (ATCC 6258), C. parapsilosis (ATCC 22019), and C. glabrata (ATCC 90030) was elucidated according to the EUCAST definitive (EDef 7.1) method. Consistent with the activity studies, 3a3d were found to be more potent derivatives with their MIC50 values (0.78 µg/mL–3.125 µg/mL) against Candida strains. Compound 3c indicated similar antifungal activity to ketoconazole against all Candida species and was evaluated as the most active derivative in the series. Effects of the most potent derivatives 3a3d on ergosterol biosynthesis were observed by LC-MS-MS method, which is based on quantification of the ergosterol level in C. krusei. Moreover, these compounds were subjected to a cytotoxicity test for the preliminary toxicological profiles and were found as non-cytotoxic. Furthermore, docking studies for the most active derivative 3c were performed to evaluate its binding modes on lanosterol 14-α-demethylase. In addition to in vitro tests, docking studies also revealed that Compound 3c is a potential ergosterol biosynthesis inhibitor. View Full-Text
Keywords: imidazole; anticandidal activity; ergosterol inhibition; 14-alpha demethylase; docking study imidazole; anticandidal activity; ergosterol inhibition; 14-alpha demethylase; docking study
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Osmaniye, D.; Kaya Cavusoglu, B.; Saglik, B.N.; Levent, S.; Acar Cevik, U.; Atli, O.; Ozkay, Y.; Kaplancikli, Z.A. Synthesis and Anticandidal Activity of New Imidazole-Chalcones. Molecules 2018, 23, 831.

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