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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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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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 |
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Snippet | Imidazole analogues of fluoxetine have been obtained by replacing the methylamino terminus of aminopropane chain with the imidazole ring. The newly designed... |
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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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