title: Synthesis of 2-substituted 17β-hydroxy/17-methylene estratrienes and their in vitro cytotoxicity in human cancer cell cultures.
abstract: Synthesis of various types of 2-(alkylaminomethyl) and 2-(aroyl) 17β-estradiol analogs are reported. The synthesis of similar types of 2-substituted 17-methylene estratriene analogs was also achieved. Synthesis of chalcone derivatives of 17β-estradiol and 17-methylene estratriene were also realized. All these 2-substituted estratrienes were tested for their antiproliferative activity by using four different cell lines from colon, lung, glioma and breast cancers. Among the various 2-substituted estratrienes, the compounds 10d, 14a-h and 17e were found to have in vitro antiproliferative activity comparable to that of parent analogs 1-4. Comparison of the SAR pattern of these 2-susbtituted estratriene derivatives confirmed that relatively, 17-methylene estratrienes are more active than that of 17β-estradiol analogs.
authors.affiliation: Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India.
authors.forename: Ganapathy
authors.initials: G
authors.lastname: Panchapakesan
authors.forename: Vasudevan
authors.initials: V
authors.lastname: Dhayalan
authors.forename: Nachiappan
authors.initials: N
authors.lastname: Dhatchana Moorthy
authors.forename: Nidhyanandan
authors.initials: N
authors.lastname: Saranya
authors.forename: Arasambattu K
authors.initials: AK
authors.lastname: Mohanakrishnan
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004958:Estradiol / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50
chemical_list: D000970:Antineoplastic Agents; D004958:Estradiol