Synthesis and Anticandidal Activity of New Imidazole-Chalcones
In the present work, 15 new 1-(4-(1H-imidazol-1-yl)phenyl)-3-(4-substituedphenyl)prop-2-en-1-one derivatives (3a–3o) were synthesized to evaluate their antifungal activity. Structures of newly synthesized imidazole derivatives (3a–3o) were characterized by IR, 1H-NMR, 13C-NMR, and LCMSMS spectroscop...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2018-04-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/23/4/831 |
| _version_ | 1818235559449985024 |
|---|---|
| author | Derya Osmaniye Betul Kaya Cavusoglu Begum Nurpelin Saglik Serkan Levent Ulviye Acar Cevik Ozlem Atli Yusuf Ozkay Zafer Asim Kaplancikli |
| author_facet | Derya Osmaniye Betul Kaya Cavusoglu Begum Nurpelin Saglik Serkan Levent Ulviye Acar Cevik Ozlem Atli Yusuf Ozkay Zafer Asim Kaplancikli |
| author_sort | Derya Osmaniye |
| collection | DOAJ |
| description | In the present work, 15 new 1-(4-(1H-imidazol-1-yl)phenyl)-3-(4-substituedphenyl)prop-2-en-1-one derivatives (3a–3o) were synthesized to evaluate their antifungal activity. Structures of newly synthesized imidazole derivatives (3a–3o) were characterized by IR, 1H-NMR, 13C-NMR, and LCMSMS spectroscopic methods. The anticandidal activity of compounds (3a–3o) 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, 3a–3d 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 3a–3d 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. |
| first_indexed | 2024-12-12T11:55:54Z |
| format | Article |
| id | doaj.art-cf1093ef070e4250b2e0bd080a8b29cf |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-12T11:55:54Z |
| publishDate | 2018-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-cf1093ef070e4250b2e0bd080a8b29cf2022-12-22T00:25:12ZengMDPI AGMolecules1420-30492018-04-0123483110.3390/molecules23040831molecules23040831Synthesis and Anticandidal Activity of New Imidazole-ChalconesDerya Osmaniye0Betul Kaya Cavusoglu1Begum Nurpelin Saglik2Serkan Levent3Ulviye Acar Cevik4Ozlem Atli5Yusuf Ozkay6Zafer Asim Kaplancikli7Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu Universty, 26470 Eskişehir, TurkeyDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu Universty, 26470 Eskişehir, TurkeyDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu Universty, 26470 Eskişehir, TurkeyDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu Universty, 26470 Eskişehir, TurkeyDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu Universty, 26470 Eskişehir, TurkeyDepartment of Pharmaceutical Toxicology, Faculty of Pharmacy, Anadolu Universty, 26470 Eskişehir, TurkeyDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu Universty, 26470 Eskişehir, TurkeyDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu Universty, 26470 Eskişehir, TurkeyIn the present work, 15 new 1-(4-(1H-imidazol-1-yl)phenyl)-3-(4-substituedphenyl)prop-2-en-1-one derivatives (3a–3o) were synthesized to evaluate their antifungal activity. Structures of newly synthesized imidazole derivatives (3a–3o) were characterized by IR, 1H-NMR, 13C-NMR, and LCMSMS spectroscopic methods. The anticandidal activity of compounds (3a–3o) 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, 3a–3d 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 3a–3d 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.http://www.mdpi.com/1420-3049/23/4/831imidazoleanticandidal activityergosterol inhibition14-alpha demethylasedocking study |
| spellingShingle | Derya Osmaniye Betul Kaya Cavusoglu Begum Nurpelin Saglik Serkan Levent Ulviye Acar Cevik Ozlem Atli Yusuf Ozkay Zafer Asim Kaplancikli Synthesis and Anticandidal Activity of New Imidazole-Chalcones Molecules imidazole anticandidal activity ergosterol inhibition 14-alpha demethylase docking study |
| title | Synthesis and Anticandidal Activity of New Imidazole-Chalcones |
| title_full | Synthesis and Anticandidal Activity of New Imidazole-Chalcones |
| title_fullStr | Synthesis and Anticandidal Activity of New Imidazole-Chalcones |
| title_full_unstemmed | Synthesis and Anticandidal Activity of New Imidazole-Chalcones |
| title_short | Synthesis and Anticandidal Activity of New Imidazole-Chalcones |
| title_sort | synthesis and anticandidal activity of new imidazole chalcones |
| topic | imidazole anticandidal activity ergosterol inhibition 14-alpha demethylase docking study |
| url | http://www.mdpi.com/1420-3049/23/4/831 |
| work_keys_str_mv | AT deryaosmaniye synthesisandanticandidalactivityofnewimidazolechalcones AT betulkayacavusoglu synthesisandanticandidalactivityofnewimidazolechalcones AT begumnurpelinsaglik synthesisandanticandidalactivityofnewimidazolechalcones AT serkanlevent synthesisandanticandidalactivityofnewimidazolechalcones AT ulviyeacarcevik synthesisandanticandidalactivityofnewimidazolechalcones AT ozlematli synthesisandanticandidalactivityofnewimidazolechalcones AT yusufozkay synthesisandanticandidalactivityofnewimidazolechalcones AT zaferasimkaplancikli synthesisandanticandidalactivityofnewimidazolechalcones |