title: Synthesis of D-ring-substituted (5'R)- and (5'S)-17β-pyrazolinylandrostene epimers and comparison of their potential anticancer activities.
abstract: Various steroidal benzylidenes were synthetized from pregnenolone with benzaldehyde and p-substituted benzaldehydes. The resulting 17β-chalconyl derivatives of pregnenolone were reacted with hydrazine hydrate in acetic acid solution. Regardless of the starting material, the ring-closure reaction afforded (in contrast with the literature data) a mixture of two steroidal pyrazoline epimers. The epimers were critical isomer pairs, which could be separated only in their acetylated form; their structures were investigated by NMR techniques. The in vitro inhibition of rat testicular C(17,20)-lyase activity and the antiproliferative effects on four human cancer cell lines were measured, and the results obtained from the two epimer series were compared.
authors.affiliation: Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
authors.forename: Zoltán
authors.initials: Z
authors.lastname: Iványi
authors.forename: Nikoletta
authors.initials: N
authors.lastname: Szabó
authors.forename: Judit
authors.initials: J
authors.lastname: Huber
authors.forename: János
authors.initials: J
authors.lastname: Wölfling
authors.forename: István
authors.initials: I
authors.lastname: Zupkó
authors.forename: Mihály
authors.initials: M
authors.lastname: Szécsi
authors.forename: Tibor
authors.initials: T
authors.lastname: Wittmann
authors.forename: Gyula
authors.initials: G
authors.lastname: Schneider
mesh_terms: D019342:Acetic Acid / Q000737:chemistry; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D006367:HeLa Cells; D006801:Humans; D006834:Hydrazines / Q000737:chemistry; D007536:Isomerism; D008297:Male; D008956:Models, Chemical; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D017208:Rats, Wistar; D013254:Steroid 17-alpha-Hydroxylase / Q000037:antagonists & inhibitors / Q000378:metabolism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013737:Testis / Q000201:enzymology
chemical_list: D000970:Antineoplastic Agents; D006834:Hydrazines; D011720:Pyrazoles; D013256:Steroids; C029424:hydrazine; D013254:Steroid 17-alpha-Hydroxylase; D019342:Acetic Acid