title: Synthesis and investigation of biological properties of modified 6-oxa-estra-1,3,5(10),8(9)-tetraenes.
abstract: To investigate the relationship between structure and biological activity of analogues of steroid estrogens we have developed the synthesis of 7α-methyl-6-oxa-estra-1,3,5(10),8(9)-tetraenes with cis- and trans-junction of C and D rings. We found that such compounds have stronger osteoprotective, cholesterol-lowering and antioxidant properties in comparison with uterotrophic activity; that is the advantage in comparison with clinically used 17α-ethynylestradiol.
authors.affiliation: Department of Natural Products Chemistry, Faculty of Chemistry, Saint-Petersburg State University, Universitetsky pr. 26, Petrodvorets 198504, Russia. Electronic address: Morozkina.Svetlana@gmail.com.
authors.forename: Svetlana N
authors.initials: SN
authors.lastname: Morozkina
authors.affiliation: Department of Natural Products Chemistry, Faculty of Chemistry, Saint-Petersburg State University, Universitetsky pr. 26, Petrodvorets 198504, Russia.
authors.forename: Anna S
authors.initials: AS
authors.lastname: Chentsova
authors.affiliation: Department of Natural Products Chemistry, Faculty of Chemistry, Saint-Petersburg State University, Universitetsky pr. 26, Petrodvorets 198504, Russia.
authors.forename: Stanislav I
authors.initials: SI
authors.lastname: Selivanov
authors.affiliation: Department of Natural Products Chemistry, Faculty of Chemistry, Saint-Petersburg State University, Universitetsky pr. 26, Petrodvorets 198504, Russia.
authors.forename: Alexander G
authors.initials: AG
authors.lastname: Shavva
mesh_terms: D000818:Animals; D000924:Anticholesteremic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015519:Bone Density / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D004963:Estrenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005260:Female; D009929:Organ Size / Q000187:drug effects; D051381:Rats; D013237:Stereoisomerism; D014599:Uterus / Q000187:drug effects / Q000254:growth & development
chemical_list: D000924:Anticholesteremic Agents; D000975:Antioxidants; D004963:Estrenes
keywords: 6-Oxa-estra-1,3,5(10),8(9)-tetraenes; Cholesterol-lowering and antioxidant properties; Decreased uterotrophic activity; Hormone replacement therapy; Osteoprotective; Stereoselectivity of hydrogenation reaction