Imidazole Analogues of Fluoxetine, a Novel Class of Anti-Candida Agents
Imidazole analogues of fluoxetine have been obtained by replacing the methylamino terminus of aminopropane chain with the imidazole ring. The newly designed imidazoles showed potent anti-Candida activity, superior to those of miconazole and other antifungal agents of clinical interest. 1-(4-Chloroph...
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| Published in | Journal of medicinal chemistry Vol. 47; no. 16; pp. 3924 - 3926 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
American Chemical Society
29.07.2004
Amer Chemical Soc |
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| Abstract | Imidazole analogues of fluoxetine have been obtained by replacing the methylamino terminus of aminopropane chain with the imidazole ring. The newly designed imidazoles showed potent anti-Candida activity, superior to those of miconazole and other antifungal agents of clinical interest. 1-(4-Chlorophenyl)-1-(2,4-dichlorophenoxy)-3-(1H-imidazol-1-yl)propane (16), the most active among test imidazoles, was about 2-fold more active and as much less cytotoxic than miconazole. High increase of activity was observed with methyl, nitro, fluorine, and chlorine (Cl > F > CH3 > NO2 > CF3). |
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| AbstractList | Imidazole analogues of fluoxetine have been obtained by replacing the methylamino terminus of aminopropane chain with the imidazole ring. The newly designed imidazoles showed potent anti-Candida activity, superior to those of miconazole and other antifungal agents of clinical interest. 1-(4-Chlorophenyl)-1-(2,4-dichlorophenoxy)-3-(1H-imidazol-1-yl)propane (16), the most active among test imidazoles, was about 2-fold more active and as much less cytotoxic than miconazole. High increase of activity was observed with methyl, nitro, fluorine, and chlorine (Cl > F > CH(3) > NO(2) > CF(3)). Imidazole analogues of fluoxetine have been obtained by replacing the methylamino terminus of aminopropane chain with the imidazole ring. The newly designed imidazoles showed potent anti-Candida activity, superior to those of miconazole and other antifungal agents of clinical interest. 1-(4-Chlorophenyl)-1-(2,4-dichlorophenoxy)-3-(1H-imidazol-1-yl)propane (16), the most active among test imidazoles, was about 2-fold more active and as much less cytotoxic than miconazole. High increase of activity was observed with methyl, nitro, fluorine, and chlorine (Cl > F > CH3 > NO2 > CF3). Imidazole analogues of fluoxetine have been obtained by replacing the methylamino terminus of aminopropane chain with the imidazole ring. The newly designed imidazoles showed potent anti-Candida activity, superior to those of miconazole and other antifungal agents of clinical interest. 1-(4-Chlorophenyl)-1-(2,4-dichlorophenoxy)-3-(1H-imidazol-1-yl)propane (16), the most active among test imidazoles, was about 2-fold more active and as much less cytotoxic than miconazole. High increase of activity was observed with methyl, nitro, fluorine, and chlorine (Cl > F > CH(3) > NO(2) > CF(3)). |
| Author | Palamara, Anna Teresa Silvestri, Romano La Regina, Giuseppe Artico, Marino Di Pasquali, Alessandra Nencioni, Lucia D'Auria, Felicia Diodata De Martino, Gabriella |
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| Cites_doi | 10.1016/S1369-5274(98)80087-8 10.1002/ardp.19893220609 10.1042/bst0190774 10.1016/S0065-7743(00)35015-1 10.1093/jac/48.6.775 10.1111/j.1439-0507.1998.tb00344.x |
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| Keywords | ANTIFUNGAL AGENTS ANTIBACTERIAL Candida albicans Five membered ring Ether Nitrogen heterocycle Benzene derivatives In vitro Fungi Antifungal agent Structure activity relation Chlorine Organic compounds Fungi Imperfecti Chemical synthesis Thallophyta |
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| References | Sheehan, DJ (WOS:000078057000004) 1999; 12 Lass-Florl, C (WOS:000172673600004) 2001; 48 Wildfeuer, A (WOS:000077373800010) 1998; 41 RYDER, NS (WOS:A1991GE10100050) 1991; 19 Artico, M (WOS:A1996UP55500001) 1996; 6 (WOS:000222856800004.1) 2001; 1 Watkins, WJ (WOS:000165049900014) 2000; 35 MASSA, S (WOS:A1989AD28900008) 1989; 322 VILLANOVA PA (WOS:000222856800004.9) 2002 WEINBERG ED (WOS:000222856800004.11) 1996; 2 STEFANCICH, G (WOS:A1992JZ63600001) 1992; 325 Georgopapadakou, NH (WOS:000076521800009) 1998; 1 Ryder N. S. (jm049856vb00006/jm049856vb00006_1) 1991; 19 Stefancich G. (jm049856vb00009/jm049856vb00009_1) 1992; 325 Massa S. (jm049856vb00008/jm049856vb00008_1) 1989; 322 Wildfeuer A. (jm049856vb00003/jm049856vb00003_1) 1998; 41 Lass-Flörl C. (jm049856vb00007/jm049856vb00007_1) 2001; 48 Artico M. (jm049856vb00010/jm049856vb00010_1) 1996; 137 Fungal Infections R (jm049856vb00002/jm049856vb00002_1) 2001; 1 Georgopapadakou N. H. (jm049856vb00004/jm049856vb00004_1) 1998; 1 jm049856vb00005/jm049856vb00005_1 jm049856vb00001/jm049856vb00001_1 Villanova P. A. (jm049856vb00011/jm049856vb00011_1) 2002 |
| References_xml | – volume: 1 start-page: 57 year: 2001 ident: WOS:000222856800004.1 publication-title: FUNGAL INFECTIONS – volume: 41 start-page: 309 year: 1998 ident: WOS:000077373800010 article-title: In vitro evaluation of voriconazole against clinical isolates of yeasts, moulds and dermatophytes in comparison with itraconazole, ketoconazole, amphotericin B and griseofulvin publication-title: MYCOSES contributor: fullname: Wildfeuer, A – volume: 12 start-page: 40 year: 1999 ident: WOS:000078057000004 article-title: Current and emerging azole antifungal agents publication-title: CLINICAL MICROBIOLOGY REVIEWS contributor: fullname: Sheehan, DJ – volume: 322 start-page: 369 year: 1989 ident: WOS:A1989AD28900008 article-title: RESEARCHES ON ANTIBACTERIAL AND ANTIFUNGAL AGENTS .10. SYNTHESIS AND ANTIFUNGAL ACTIVITIES OF 1-(PARA-METHYL-ALPHA-[4-(1H-PYRROL-1-YL)PHENYL]BENZYL)AZOLES AND SOME RELATED PRODUCTS publication-title: ARCHIV DER PHARMAZIE contributor: fullname: MASSA, S – volume: 6 start-page: 137 year: 1996 ident: WOS:A1996UP55500001 article-title: Iso-miconazole and related derivatives: Synthesis and antifungal activities publication-title: MEDICINAL CHEMISTRY RESEARCH contributor: fullname: Artico, M – volume: 35 start-page: 157 year: 2000 ident: WOS:000165049900014 article-title: Progress with antifungal agents and approaches to combat fungal resistance publication-title: ANNUAL REPORTS IN MEDICINAL CHEMISTRY, VOL 35 contributor: fullname: Watkins, WJ – volume: 19 start-page: 774 year: 1991 ident: WOS:A1991GE10100050 article-title: SQUALENE EPOXIDASE AS A TARGET FOR THE ALLYLAMINES publication-title: BIOCHEMICAL SOCIETY TRANSACTIONS contributor: fullname: RYDER, NS – volume: 2 start-page: 637 year: 1996 ident: WOS:000222856800004.11 publication-title: BURGERS MED CHEM DRU contributor: fullname: WEINBERG ED – volume: 325 start-page: 687 year: 1992 ident: WOS:A1992JZ63600001 article-title: ANTIBACTERIAL AND ANTIFUNGAL AGENTS .15. SYNTHESIS AND ANTIFUNGAL ACTIVITY OF STRUCTURAL ANALOGS OF BIFONAZOLE AND KETOCONAZOLE publication-title: ARCHIV DER PHARMAZIE contributor: fullname: STEFANCICH, G – year: 2002 ident: WOS:000222856800004.9 publication-title: M27A2 NATL COMM CLIN contributor: fullname: VILLANOVA PA – volume: 48 start-page: 775 year: 2001 ident: WOS:000172673600004 article-title: Antifungal properties of selective serotonin reuptake inhibitors against Aspergillus species in vitro publication-title: JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY contributor: fullname: Lass-Florl, C – volume: 1 start-page: 547 year: 1998 ident: WOS:000076521800009 article-title: Antifungals: mechanism of action and resistance, established and novel drugs publication-title: CURRENT OPINION IN MICROBIOLOGY contributor: fullname: Georgopapadakou, NH – volume: 1 start-page: 66 year: 2001 ident: jm049856vb00002/jm049856vb00002_1 publication-title: Backgrounder contributor: fullname: Fungal Infections R – volume: 1 start-page: 557 year: 1998 ident: jm049856vb00004/jm049856vb00004_1 publication-title: Curr. Opin. Microbiol. doi: 10.1016/S1369-5274(98)80087-8 contributor: fullname: Georgopapadakou N. H. – volume: 325 start-page: 694 year: 1992 ident: jm049856vb00009/jm049856vb00009_1 publication-title: Arch. Pharm. (Weinheim) contributor: fullname: Stefancich G. – volume: 322 start-page: 373 year: 1989 ident: jm049856vb00008/jm049856vb00008_1 publication-title: Arch. Pharm. (Weinheim) doi: 10.1002/ardp.19893220609 contributor: fullname: Massa S. – volume: 19 start-page: 777 year: 1991 ident: jm049856vb00006/jm049856vb00006_1 publication-title: Biochem. Soc. Trans. doi: 10.1042/bst0190774 contributor: fullname: Ryder N. S. – ident: jm049856vb00005/jm049856vb00005_1 doi: 10.1016/S0065-7743(00)35015-1 – volume: 48 start-page: 779 year: 2001 ident: jm049856vb00007/jm049856vb00007_1 publication-title: J. Antimicrob. Chemother. doi: 10.1093/jac/48.6.775 contributor: fullname: Lass-Flörl C. – volume: 41 start-page: 319 year: 1998 ident: jm049856vb00003/jm049856vb00003_1 publication-title: Mycoses doi: 10.1111/j.1439-0507.1998.tb00344.x contributor: fullname: Wildfeuer A. – ident: jm049856vb00001/jm049856vb00001_1 – volume-title: Reference method for broth dilution antifungal susceptibility testing of yeast: aprroved standard. National Committee for Clinical Laboratory Standards year: 2002 ident: jm049856vb00011/jm049856vb00011_1 contributor: fullname: Villanova P. A. – volume: 137 start-page: 147 year: 1996 ident: jm049856vb00010/jm049856vb00010_1 publication-title: Med. Chem. Res. contributor: fullname: Artico M. |
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| SubjectTerms | Antibiotics. Antiinfectious agents. Antiparasitic agents Antifungal agents Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Antifungal Agents - pharmacology Biological and medical sciences Candida albicans - drug effects Cell Line, Tumor Cell Survival - drug effects Chemistry, Medicinal Fluoxetine - analogs & derivatives Fluoxetine - chemical synthesis Fluoxetine - pharmacology Humans Imidazoles - chemical synthesis Imidazoles - pharmacology Life Sciences & Biomedicine Medical sciences Microbial Sensitivity Tests Pharmacology & Pharmacy Pharmacology. Drug treatments Science & Technology Structure-Activity Relationship |
| Title | Imidazole Analogues of Fluoxetine, a Novel Class of Anti-Candida Agents |
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