No Cover Image

Journal article 635 views

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 Orcid Logo, 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 Orcid Logo

Full text not available from this repository: check for access using links below.

Check full text

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...

Full description

Published in: Journal of Medicinal Chemistry
ISSN: 0022-2623 1520-4804
Published: American Chemical Society (ACS) 2008
Online Access: Check full text

URI: https://cronfa.swan.ac.uk/Record/cronfa10336
Tags: Add Tag
No Tags, Be the first to tag this record!
first_indexed 2013-07-23T12:03:16Z
last_indexed 2021-10-30T02:21:29Z
id cronfa10336
recordtype SURis
fullrecord <?xml version="1.0"?><rfc1807><datestamp>2021-10-29T09:38:20.4124954</datestamp><bib-version>v2</bib-version><id>10336</id><entry>2012-03-21</entry><title>1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, New Imidazoles with Potent Activity againstCandida albicansand Dermatophytes. Synthesis, Structure&#x2212;Activity Relationship, and Molecular Modeling Studies</title><swanseaauthors><author><sid>b17cebaf09b4d737b9378a3581e3de93</sid><ORCID>0000-0001-7991-5040</ORCID><firstname>Steven</firstname><surname>Kelly</surname><name>Steven Kelly</name><active>true</active><ethesisStudent>false</ethesisStudent></author></swanseaauthors><date>2012-03-21</date><deptcode>BMS</deptcode><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 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 &lt;= 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.</abstract><type>Journal Article</type><journal>Journal of Medicinal Chemistry</journal><volume>51</volume><journalNumber>13</journalNumber><paginationStart>3841</paginationStart><paginationEnd>3855</paginationEnd><publisher>American Chemical Society (ACS)</publisher><placeOfPublication/><isbnPrint/><isbnElectronic/><issnPrint>0022-2623</issnPrint><issnElectronic>1520-4804</issnElectronic><keywords>AZOLE ANTIFUNGAL AGENTS; ANTICANDIDA ACTIVITY; BINDING; DERIVATIVES; FLUOXETINE; RESISTANCE; ANALOGS; DRUGS; CYP51</keywords><publishedDay>1</publishedDay><publishedMonth>7</publishedMonth><publishedYear>2008</publishedYear><publishedDate>2008-07-01</publishedDate><doi>10.1021/jm800009r</doi><url/><notes/><college>COLLEGE NANME</college><department>Biomedical Sciences</department><CollegeCode>COLLEGE CODE</CollegeCode><DepartmentCode>BMS</DepartmentCode><institution>Swansea University</institution><apcterm/><lastEdited>2021-10-29T09:38:20.4124954</lastEdited><Created>2012-03-21T16:17:29.0000000</Created><path><level id="1">Swansea University Medical School</level><level id="2">Medicine</level></path><authors><author><firstname>Giuseppe La</firstname><surname>Regina</surname><order>1</order></author><author><firstname>Felicia Diodata</firstname><surname>D&#x2019;Auria</surname><order>2</order></author><author><firstname>Andrea</firstname><surname>Tafi</surname><order>3</order></author><author><firstname>Francesco</firstname><surname>Piscitelli</surname><order>4</order></author><author><firstname>Stefania</firstname><surname>Olla</surname><order>5</order></author><author><firstname>Fabiana</firstname><surname>Caporuscio</surname><order>6</order></author><author><firstname>Lucia</firstname><surname>Nencioni</surname><order>7</order></author><author><firstname>Roberto</firstname><surname>Cirilli</surname><order>8</order></author><author><firstname>Francesco La</firstname><surname>Torre</surname><order>9</order></author><author><firstname>Nadja Rodrigues De</firstname><surname>Melo</surname><order>10</order></author><author><firstname>Steven</firstname><surname>Kelly</surname><orcid>0000-0001-7991-5040</orcid><order>11</order></author><author><firstname>David C.</firstname><surname>Lamb</surname><order>12</order></author><author><firstname>Marino</firstname><surname>Artico</surname><order>13</order></author><author><firstname>Maurizio</firstname><surname>Botta</surname><order>14</order></author><author><firstname>Anna Teresa</firstname><surname>Palamara</surname><order>15</order></author><author><firstname>Romano</firstname><surname>Silvestri</surname><order>16</order></author></authors><documents/><OutputDurs/></rfc1807>
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 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 Swansea University Medical School
hierarchytype
hierarchy_top_id swanseauniversitymedicalschool
hierarchy_top_title Swansea University Medical School
hierarchy_parent_id swanseauniversitymedicalschool
hierarchy_parent_title Swansea University Medical School
department_str Medicine{{{_:::_}}}Swansea University Medical School{{{_:::_}}}Medicine
document_store_str 0
active_str 0
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 2008-07-01T03:19:17Z
_version_ 1737024400098590720
score 10.89968