title: Steroidal pyrazolines and pyrazoles as potential 5α-reductase inhibitors: synthesis and biological evaluation.
abstract: Taking pregnenolone as the starting material, two series of pyrazolinyl and pyrazolyl pregnenolones were synthesized through different routes. The synthesis of the analogs of both series is multistep and proceeds in good overall yields. While the key step in the synthesis of pyrazolinyl pregnenolones is the heterocyclization of benzylidine derivatives (3) in presence of hydrazine hydrate, it is the condensation of 3β-hydroxy-21-hydroxymethylidenepregn-5-en-3β-ol-20-one (5) with phenylhydrazine in the synthesis of pyrazolyl derivatives. Compounds of both the series were tested for their 5α-reductase inhibitory activities. Amongst all the compounds screened for their 5α-reductase inhibitory activities, compound 4b, 4c and 6b were found to be the most active.
authors.affiliation: Department of Chemistry, Islamia College of Science and Commerce, Srinagar 190009, India; Department of Chemistry and Biochemistry, University of Arizona, Tucson 85721, USA. Electronic address: abidrrl@gmail.com.
authors.forename: Abid H
authors.initials: AH
authors.lastname: Banday
authors.affiliation: Department of Chemistry, Islamia College of Science and Commerce, Srinagar 190009, India.
authors.forename: Shameem A
authors.initials: SA
authors.lastname: Shameem
authors.affiliation: Department of Chemistry, University of Kashmir, Hazratbal, Srinagar 190002, India.
authors.forename: Salika
authors.initials: S
authors.lastname: Jeelani
mesh_terms: D058891:5-alpha Reductase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry*; D018120:Finasteride / Q000138:chemical synthesis / Q000737:chemistry; D006801:Humans; D008297:Male; D011284:Pregnenolone / Q000737:chemistry; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D058891:5-alpha Reductase Inhibitors; D011720:Pyrazoles; D018120:Finasteride; D011284:Pregnenolone
keywords: 5α-reductase inhibition; Benzylidines; Pregnenolone; Pyrazoles; Pyrazoline