Abstract
We herein report the synthesis of 3β-substituted amides of 17a-aza-D-homo-4-androsten-17-one (11a-11r) from commercially available Diosgenin as the starting material. The structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and mass spectrometry. All the synthesized analogues were tested for their 5α- reductase inhibitory and antimicrobial activity, some of them exhibit moderate to potent activity comparable to the reference drugs. Among the synthesized derivatives the analogue (11r) 3β-(indonlylbutanamido)-17a-aza-D-homo-4- androsten-17-one was found to be active against both 5-reductase enzyme and microbial strains, whereas the analogue (11i) 3β-(3,4-dimethoxy-benzamido)-17a-aza-D-homo-4-androsten-17-one was found to be the least active. The detailed 5-reductase inhibitors and antimicrobial activities of the synthesized compounds were reported.
Keywords: 5α-Reductase, Antibacterial, Antifungal, Dutasteride, Ciprofloxacin, Voriconazole.
Current Topics in Medicinal Chemistry
Title:Synthesis and Characterization of 3β-Substituted Amides of 17a-Aza-Dhomo- 4-androsten-17-one as Potent 5α-Reductase Inhibitors and Antimicrobial Agents
Volume: 13 Issue: 16
Author(s): Manav Malhotra, Rajiv Sharma, Ravindra K. Rawal, Hemraj Heer and T. R. Bhardwaj
Affiliation:
Keywords: 5α-Reductase, Antibacterial, Antifungal, Dutasteride, Ciprofloxacin, Voriconazole.
Abstract: We herein report the synthesis of 3β-substituted amides of 17a-aza-D-homo-4-androsten-17-one (11a-11r) from commercially available Diosgenin as the starting material. The structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and mass spectrometry. All the synthesized analogues were tested for their 5α- reductase inhibitory and antimicrobial activity, some of them exhibit moderate to potent activity comparable to the reference drugs. Among the synthesized derivatives the analogue (11r) 3β-(indonlylbutanamido)-17a-aza-D-homo-4- androsten-17-one was found to be active against both 5-reductase enzyme and microbial strains, whereas the analogue (11i) 3β-(3,4-dimethoxy-benzamido)-17a-aza-D-homo-4-androsten-17-one was found to be the least active. The detailed 5-reductase inhibitors and antimicrobial activities of the synthesized compounds were reported.
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Cite this article as:
Malhotra Manav, Sharma Rajiv, Rawal K. Ravindra, Heer Hemraj and Bhardwaj R. T., Synthesis and Characterization of 3β-Substituted Amides of 17a-Aza-Dhomo- 4-androsten-17-one as Potent 5α-Reductase Inhibitors and Antimicrobial Agents, Current Topics in Medicinal Chemistry 2013; 13 (16) . https://dx.doi.org/10.2174/15680266113139990131
DOI https://dx.doi.org/10.2174/15680266113139990131 |
Print ISSN 1568-0266 |
Publisher Name Bentham Science Publisher |
Online ISSN 1873-4294 |
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