title: Synthesis and characterization of 3β-substituted amides of 17a-aza-D-homo- 4-androsten-17-one as potent 5α-reductase inhibitors and antimicrobial agents.
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, (1)H NMR, (13)C 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 5α-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 5α-reductase inhibitors and antimicrobial activities of the synthesized compounds were reported.
authors.affiliation: Department of Pharmaceutical Chemistry, Indo-Soviet Friendship (ISF) College of Pharmacy, Ferozepur Road, Moga-142 001, India. manavmalhotra99@yahoo.in
authors.forename: Manav
authors.initials: M
authors.lastname: Malhotra
authors.forename: Rajiv
authors.initials: R
authors.lastname: Sharma
authors.forename: Ravindra K
authors.initials: RK
authors.lastname: Rawal
authors.forename: Hemraj
authors.initials: H
authors.lastname: Heer
authors.forename: T R
authors.initials: TR
authors.lastname: Bhardwaj
mesh_terms: D058891:5-alpha Reductase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000577:Amides / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001378:Azasteroids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D042944:Cholestenone 5 alpha-Reductase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D004305:Dose-Response Relationship, Drug; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: C000592350:3-(indonlylbutanamido)-17a-azahomo-4-androsten-17-one; D058891:5-alpha Reductase Inhibitors; D000577:Amides; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001378:Azasteroids; D042944:Cholestenone 5 alpha-Reductase