Synthesis and Characterization of 3β-Substituted Amides of 17a-Aza-Dhomo- 4-androsten-17-one as Potent 5α-Reductase Inhibitors and Antimicrobial Agents

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.

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