title: Heterocyclic ring extension of androstenedione: synthesis and cytotoxicity of fused pyran, pyrimidine and thiazole derivatives.
abstract: The reaction of androstenedione with either malononitrile or ethyl cyanoacetate and aromatic aldehydes 2a-c gave the pyran derivatives 4a-f, respectively. On the other hand, the reaction of androstenedione with thiourea and the aromatic aldehydes 2a-c gave the pyrimidine derivatives 6a-c, respectively. Compound 6b reacted with 2-bromo-1-arylethanone derivatives 7a-d to give the indeno[2,1-e]thiazole derivatives 8a-d. Some of the produced compounds were used for further heterocyclization reactions. The cytotoxicity of the newly obtained products was evaluated against some cancer cell lines and a normal cell line.
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.affiliation: Department of Chemistry, Faculty of Science, Helwan University, Cairo, Egypt.
authors.forename: Nermeen S
authors.initials: NS
authors.lastname: Abbas
authors.affiliation: Department of Chemistry, Faculty of Science, Tabuk University, P.O. Box 741, Tabuk 71491, Kingdom of Saudi Arabia; Basic Science Department, Modern Academy For Engineering and Technology in Maadi, Egypt.
authors.forename: Mahmoud A
authors.initials: MA
authors.lastname: Abdelaziz
mesh_terms: D000735:Androstenedione / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D049109:Cell Proliferation / Q000187:drug effects; D002478:Cells, Cultured; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical; D005347:Fibroblasts / Q000187:drug effects*; D056945:Hep G2 Cells; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D006801:Humans; D061986:MCF-7 Cells; D008968:Molecular Conformation; D011714:Pyrans / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000737:chemistry*
chemical_list: D006571:Heterocyclic Compounds; D011714:Pyrans; D011743:Pyrimidines; D013844:Thiazoles; D000735:Androstenedione; C030986:pyrimidine
keywords: Androstenedione; Cytotoxicity; Pyran; Pyrimidine; Thieno[2,3-b]pyridine