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1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, New Imidazoles with Potent Activity againstCandida albicansand Dermatophytes. Synthesis, Structure−Activity Relationship, and Molecular Modeling Studies
Giuseppe La Regina,
Felicia Diodata D’Auria,
Andrea Tafi,
Francesco Piscitelli,
Stefania Olla,
Fabiana Caporuscio,
Lucia Nencioni,
Roberto Cirilli,
Francesco La Torre,
Nadja Rodrigues De Melo,
Steven Kelly 
,
David C. Lamb,
Marino Artico,
Maurizio Botta,
Anna Teresa Palamara,
Romano Silvestri
,
David C. Lamb,
Marino Artico,
Maurizio Botta,
Anna Teresa Palamara,
Romano Silvestri
Journal of Medicinal Chemistry, Volume: 51, Issue: 13, Pages: 3841 - 3855
Swansea University Author:
Steven Kelly
Full text not available from this repository: check for access using links below.
DOI (Published version): 10.1021/jm800009r
Abstract
New 1-[(3-aryloxy-3-aryl)propyl]-1H-imidazoles were synthesized and evaluated against Candida albicans and dermatophytes in order to develop structure-activity relationships (SARs). Against C. albicans the new imidazoles showed minimal inhibitory concentrations (MICs) comparable to those of ketocona...
| Published in: | Journal of Medicinal Chemistry |
|---|---|
| ISSN: | 0022-2623 1520-4804 |
| Published: |
American Chemical Society (ACS)
2008
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| URI: | https://cronfa.swan.ac.uk/Record/cronfa10336 |
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| spelling |
2021-10-29T09:38:20.4124954 v2 10336 2012-03-21 1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, New Imidazoles with Potent Activity againstCandida albicansand Dermatophytes. Synthesis, Structure−Activity Relationship, and Molecular Modeling Studies b17cebaf09b4d737b9378a3581e3de93 0000-0001-7991-5040 Steven Kelly Steven Kelly true false 2012-03-21 BMS New 1-[(3-aryloxy-3-aryl)propyl]-1H-imidazoles were synthesized and evaluated against Candida albicans and dermatophytes in order to develop structure-activity relationships (SARs). Against C. albicans the new imidazoles showed minimal inhibitory concentrations (MICs) comparable to those of ketoconazole, miconazole, and econazole, and were more potent than fluconazole. Several derivatives (10, 12, 14, 18-20, 24, 28, 29, 30, and 34) turned out to be potent inhibitors of C. albicans strains resistant to fluconazole, with MIC values less than 10 mu g/mL. Against dermatophytes strains, compounds 20, 25, and 33 (MIC <= 5 mu g/mL) were equipotent to ketoconazole, econazole, and miconazole. SARs of imidazoles 10-44 were rationalized with reasonable accuracy by a previously developed quantitative pharmacophore for antifungal agents. Journal Article Journal of Medicinal Chemistry 51 13 3841 3855 American Chemical Society (ACS) 0022-2623 1520-4804 AZOLE ANTIFUNGAL AGENTS; ANTICANDIDA ACTIVITY; BINDING; DERIVATIVES; FLUOXETINE; RESISTANCE; ANALOGS; DRUGS; CYP51 1 7 2008 2008-07-01 10.1021/jm800009r COLLEGE NANME Biomedical Sciences COLLEGE CODE BMS Swansea University 2021-10-29T09:38:20.4124954 2012-03-21T16:17:29.0000000 Faculty of Medicine, Health and Life Sciences Swansea University Medical School - Medicine Giuseppe La Regina 1 Felicia Diodata D’Auria 2 Andrea Tafi 3 Francesco Piscitelli 4 Stefania Olla 5 Fabiana Caporuscio 6 Lucia Nencioni 7 Roberto Cirilli 8 Francesco La Torre 9 Nadja Rodrigues De Melo 10 Steven Kelly 0000-0001-7991-5040 11 David C. Lamb 12 Marino Artico 13 Maurizio Botta 14 Anna Teresa Palamara 15 Romano Silvestri 16 |
| title |
1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, New Imidazoles with Potent Activity againstCandida albicansand Dermatophytes. Synthesis, Structure−Activity Relationship, and Molecular Modeling Studies |
| spellingShingle |
1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, New Imidazoles with Potent Activity againstCandida albicansand Dermatophytes. Synthesis, Structure−Activity Relationship, and Molecular Modeling Studies Steven Kelly |
| title_short |
1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, New Imidazoles with Potent Activity againstCandida albicansand Dermatophytes. Synthesis, Structure−Activity Relationship, and Molecular Modeling Studies |
| title_full |
1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, New Imidazoles with Potent Activity againstCandida albicansand Dermatophytes. Synthesis, Structure−Activity Relationship, and Molecular Modeling Studies |
| title_fullStr |
1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, New Imidazoles with Potent Activity againstCandida albicansand Dermatophytes. Synthesis, Structure−Activity Relationship, and Molecular Modeling Studies |
| title_full_unstemmed |
1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, New Imidazoles with Potent Activity againstCandida albicansand Dermatophytes. Synthesis, Structure−Activity Relationship, and Molecular Modeling Studies |
| title_sort |
1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, New Imidazoles with Potent Activity againstCandida albicansand Dermatophytes. Synthesis, Structure−Activity Relationship, and Molecular Modeling Studies |
| author_id_str_mv |
b17cebaf09b4d737b9378a3581e3de93 |
| author_id_fullname_str_mv |
b17cebaf09b4d737b9378a3581e3de93_***_Steven Kelly |
| author |
Steven Kelly |
| author2 |
Giuseppe La Regina Felicia Diodata D’Auria Andrea Tafi Francesco Piscitelli Stefania Olla Fabiana Caporuscio Lucia Nencioni Roberto Cirilli Francesco La Torre Nadja Rodrigues De Melo Steven Kelly David C. Lamb Marino Artico Maurizio Botta Anna Teresa Palamara Romano Silvestri |
| format |
Journal article |
| container_title |
Journal of Medicinal Chemistry |
| container_volume |
51 |
| container_issue |
13 |
| container_start_page |
3841 |
| publishDate |
2008 |
| institution |
Swansea University |
| issn |
0022-2623 1520-4804 |
| doi_str_mv |
10.1021/jm800009r |
| publisher |
American Chemical Society (ACS) |
| college_str |
Faculty of Medicine, Health and Life Sciences |
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|
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facultyofmedicinehealthandlifesciences |
| hierarchy_top_title |
Faculty of Medicine, Health and Life Sciences |
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facultyofmedicinehealthandlifesciences |
| hierarchy_parent_title |
Faculty of Medicine, Health and Life Sciences |
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Swansea University Medical School - Medicine{{{_:::_}}}Faculty of Medicine, Health and Life Sciences{{{_:::_}}}Swansea University Medical School - Medicine |
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0 |
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| description |
New 1-[(3-aryloxy-3-aryl)propyl]-1H-imidazoles were synthesized and evaluated against Candida albicans and dermatophytes in order to develop structure-activity relationships (SARs). Against C. albicans the new imidazoles showed minimal inhibitory concentrations (MICs) comparable to those of ketoconazole, miconazole, and econazole, and were more potent than fluconazole. Several derivatives (10, 12, 14, 18-20, 24, 28, 29, 30, and 34) turned out to be potent inhibitors of C. albicans strains resistant to fluconazole, with MIC values less than 10 mu g/mL. Against dermatophytes strains, compounds 20, 25, and 33 (MIC <= 5 mu g/mL) were equipotent to ketoconazole, econazole, and miconazole. SARs of imidazoles 10-44 were rationalized with reasonable accuracy by a previously developed quantitative pharmacophore for antifungal agents. |
| published_date |
2008-07-01T03:11:41Z |
| _version_ |
1763750027360993280 |
| score |
11.013148 |