Synthesis and antifungal activity of bile acid-derived oxazoles
Peracetylated bile acids (1a-g) were used as starting materials for the preparation of fourteen new derivatives bearing an oxazole moiety in their side chain (6a-g, 8a-g). The key step for the synthetic path was a Dakin-West reaction followed by a Robinson-Gabriel cyclodehydration. A simpler model o...
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todo:paper_0039128X_v108_n_p68_Fernandez2023-10-03T14:49:18Z Synthesis and antifungal activity of bile acid-derived oxazoles Fernández, L.R. Svetaz, L. Butassi, E. Zacchino, S.A. Palermo, J.A. Sánchez, M. Bile acids Candida albicans Dakin-West reaction Oxazoles amphotericin B antifungal agent bile acid methyl 2 (2,5 dimethyloxazol 4 yl)acetate methyl [5 methyl 2 (3alpha acetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,12alpha diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,12alpha dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha,7alpha triacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha,7alpha trihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha,12alpha triacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha,12alpha trihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7beta diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7beta dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,hydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate oxazole derivative unclassified drug antifungal agent bile acid oxazole derivative antifungal activity Article Candida albicans covalent bond deacetylation drug mechanism drug synthesis fungal strain fungus growth growth inhibition lipophilicity nonhuman chemistry drug effects molecular weight synthesis Antifungal Agents Bile Acids and Salts Candida albicans Chemistry Techniques, Synthetic Molecular Weight Oxazoles Peracetylated bile acids (1a-g) were used as starting materials for the preparation of fourteen new derivatives bearing an oxazole moiety in their side chain (6a-g, 8a-g). The key step for the synthetic path was a Dakin-West reaction followed by a Robinson-Gabriel cyclodehydration. A simpler model oxazole (12) was also synthesized. The antifungal activity of the new compounds (6a-g) as well as their starting bile acids (1a-g) was tested against Candida albicans. Compounds 6e and 6g showed the highest percentages of inhibition (63.84% and 61.40% at 250 μg/mL respectively). Deacetylation of compounds 6a-g, led to compounds 8a-g which showed lower activities than the acetylated derivatives. © 2016 Elsevier Inc. All rights reserved. Fil:Palermo, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_0039128X_v108_n_p68_Fernandez |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Bile acids Candida albicans Dakin-West reaction Oxazoles amphotericin B antifungal agent bile acid methyl 2 (2,5 dimethyloxazol 4 yl)acetate methyl [5 methyl 2 (3alpha acetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,12alpha diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,12alpha dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha,7alpha triacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha,7alpha trihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha,12alpha triacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha,12alpha trihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7beta diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7beta dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,hydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate oxazole derivative unclassified drug antifungal agent bile acid oxazole derivative antifungal activity Article Candida albicans covalent bond deacetylation drug mechanism drug synthesis fungal strain fungus growth growth inhibition lipophilicity nonhuman chemistry drug effects molecular weight synthesis Antifungal Agents Bile Acids and Salts Candida albicans Chemistry Techniques, Synthetic Molecular Weight Oxazoles |
| spellingShingle |
Bile acids Candida albicans Dakin-West reaction Oxazoles amphotericin B antifungal agent bile acid methyl 2 (2,5 dimethyloxazol 4 yl)acetate methyl [5 methyl 2 (3alpha acetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,12alpha diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,12alpha dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha,7alpha triacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha,7alpha trihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha,12alpha triacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha,12alpha trihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7beta diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7beta dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,hydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate oxazole derivative unclassified drug antifungal agent bile acid oxazole derivative antifungal activity Article Candida albicans covalent bond deacetylation drug mechanism drug synthesis fungal strain fungus growth growth inhibition lipophilicity nonhuman chemistry drug effects molecular weight synthesis Antifungal Agents Bile Acids and Salts Candida albicans Chemistry Techniques, Synthetic Molecular Weight Oxazoles Fernández, L.R. Svetaz, L. Butassi, E. Zacchino, S.A. Palermo, J.A. Sánchez, M. Synthesis and antifungal activity of bile acid-derived oxazoles |
| topic_facet |
Bile acids Candida albicans Dakin-West reaction Oxazoles amphotericin B antifungal agent bile acid methyl 2 (2,5 dimethyloxazol 4 yl)acetate methyl [5 methyl 2 (3alpha acetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,12alpha diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,12alpha dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha,7alpha triacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,6alpha,7alpha trihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha,12alpha triacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7alpha,12alpha trihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7beta diacetoxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,7beta dihydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate methyl [5 methyl 2 (3alpha,hydroxy 24 nor 5beta cholan 23 yl) 1,3 oxazol 4 yl]acetate oxazole derivative unclassified drug antifungal agent bile acid oxazole derivative antifungal activity Article Candida albicans covalent bond deacetylation drug mechanism drug synthesis fungal strain fungus growth growth inhibition lipophilicity nonhuman chemistry drug effects molecular weight synthesis Antifungal Agents Bile Acids and Salts Candida albicans Chemistry Techniques, Synthetic Molecular Weight Oxazoles |
| description |
Peracetylated bile acids (1a-g) were used as starting materials for the preparation of fourteen new derivatives bearing an oxazole moiety in their side chain (6a-g, 8a-g). The key step for the synthetic path was a Dakin-West reaction followed by a Robinson-Gabriel cyclodehydration. A simpler model oxazole (12) was also synthesized. The antifungal activity of the new compounds (6a-g) as well as their starting bile acids (1a-g) was tested against Candida albicans. Compounds 6e and 6g showed the highest percentages of inhibition (63.84% and 61.40% at 250 μg/mL respectively). Deacetylation of compounds 6a-g, led to compounds 8a-g which showed lower activities than the acetylated derivatives. © 2016 Elsevier Inc. All rights reserved. |
| format |
JOUR |
| author |
Fernández, L.R. Svetaz, L. Butassi, E. Zacchino, S.A. Palermo, J.A. Sánchez, M. |
| author_facet |
Fernández, L.R. Svetaz, L. Butassi, E. Zacchino, S.A. Palermo, J.A. Sánchez, M. |
| author_sort |
Fernández, L.R. |
| title |
Synthesis and antifungal activity of bile acid-derived oxazoles |
| title_short |
Synthesis and antifungal activity of bile acid-derived oxazoles |
| title_full |
Synthesis and antifungal activity of bile acid-derived oxazoles |
| title_fullStr |
Synthesis and antifungal activity of bile acid-derived oxazoles |
| title_full_unstemmed |
Synthesis and antifungal activity of bile acid-derived oxazoles |
| title_sort |
synthesis and antifungal activity of bile acid-derived oxazoles |
| url |
http://hdl.handle.net/20.500.12110/paper_0039128X_v108_n_p68_Fernandez |
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