Imidazolylchromanones containing non-benzylic oxime ethers : synthesis and molecular modeling study of new azole antifungals selective against Cryptococcus gattii
Copyright © 2014 Elsevier Masson SAS. All rights reserved..
A series of imidazolylchromanone oximes containing phenoxyethyl ether moiety, as found in omoconazole, were synthesized and evaluated against yeasts (Candida albicans and Cryptococcus gattii) and filamentous fungi (Aspergillus fumigatus and Exophiala dermatitidis). Although the title compounds showed marginal activity against filamentous fungi but all of them exhibited potent activity against C. gattii (MIC values ≤4 μg/mL). Among them, (3-chlorophenoxy)ethyl analog 7c with MIC value of 0.5 μg/mL was the most potent compound. Further molecular docking studies provided a better insight into the binding of designed compounds within the homology modeled active site of CnCYP51 (Cryptococcus CYP51-14α-demethylase).
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2014 |
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| Erschienen: |
2014 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:76 |
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| Enthalten in: |
European journal of medicinal chemistry - 76(2014) vom: 09. Apr., Seite 264-73 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Babazadeh-Qazijahani, Mojtaba [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 03.12.2014 Date Revised 10.12.2019 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.ejmech.2014.02.019 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM235983470 |
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| 100 | 1 | |a Babazadeh-Qazijahani, Mojtaba |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Imidazolylchromanones containing non-benzylic oxime ethers |b synthesis and molecular modeling study of new azole antifungals selective against Cryptococcus gattii |
| 264 | 1 | |c 2014 | |
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| 500 | |a Date Completed 03.12.2014 | ||
| 500 | |a Date Revised 10.12.2019 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2014 Elsevier Masson SAS. All rights reserved. | ||
| 520 | |a A series of imidazolylchromanone oximes containing phenoxyethyl ether moiety, as found in omoconazole, were synthesized and evaluated against yeasts (Candida albicans and Cryptococcus gattii) and filamentous fungi (Aspergillus fumigatus and Exophiala dermatitidis). Although the title compounds showed marginal activity against filamentous fungi but all of them exhibited potent activity against C. gattii (MIC values ≤4 μg/mL). Among them, (3-chlorophenoxy)ethyl analog 7c with MIC value of 0.5 μg/mL was the most potent compound. Further molecular docking studies provided a better insight into the binding of designed compounds within the homology modeled active site of CnCYP51 (Cryptococcus CYP51-14α-demethylase) | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a Antifungal activity | |
| 650 | 4 | |a Azole antifungals | |
| 650 | 4 | |a Chroman-4-one | |
| 650 | 4 | |a Cryptococcus | |
| 650 | 4 | |a Imidazole | |
| 650 | 4 | |a Lanosterol 14α-demethylase | |
| 650 | 7 | |a Antifungal Agents |2 NLM | |
| 650 | 7 | |a Azoles |2 NLM | |
| 650 | 7 | |a Chromans |2 NLM | |
| 650 | 7 | |a Sterol 14-Demethylase |2 NLM | |
| 650 | 7 | |a EC 1.14.14.154 |2 NLM | |
| 700 | 1 | |a Badali, Hamid |e verfasserin |4 aut | |
| 700 | 1 | |a Irannejad, Hamid |e verfasserin |4 aut | |
| 700 | 1 | |a Afsarian, Mohammad Hosein |e verfasserin |4 aut | |
| 700 | 1 | |a Emami, Saeed |e verfasserin |4 aut | |
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