title: The Knoevenagel reactions of pregnenolone with cyanomethylene reagents: synthesis of thiophene, thieno[2,3-b]pyridine, thieno[3,2-d]isoxazole derivatives of pregnenolone and their in vitro cytotoxicity towards tumor and normal cell lines.
abstract: The reaction of pregnenolone with either 2-aminoprop-1-ene-1,1,3-tricarbonitrile or 3-oxo-3-phenylpropanenitrile gave the Knoevenagel condensation products 3 and 6, respectively. Separation of the E and Z isomeric compounds of 3 and 6 together with their structure elucidation were carried out. Some chemical transformations of the latter products were carried out and the cytotoxicity of the newly obtained products was evaluated against some cancer cell lines and a human normal cell line. The results indicated that compounds 15, 17a, 18 and 20e among the tested compounds showed the highest cytotoxicity against the cancer cell lines.
authors.affiliation: Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt. Electronic address: raafat_mohareb@yahoo.com.
authors.forename: Rafat M
authors.initials: RM
authors.lastname: Mohareb
authors.forename: Nahed N E
authors.initials: NN
authors.lastname: El-Sayed
authors.forename: Mahmoud A
authors.initials: MA
authors.lastname: Abdelaziz
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D011284:Pregnenolone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D013876:Thiophenes; D011284:Pregnenolone
keywords: Cyanomethylene; Cytotoxicity; Fused thiophene; Pregnenolone; Thiophene