Remarkable effect of 2α-modification on the VDR antagonistic activity of 1α-hydroxyvitamin D3-26,23-lactones

Nozomi Saito; Toshihiro Matsunaga; Toshie Fujishima; Miyuki Anzai; Hiroshi Saito; Kazuya Takenouchi; Daishiro Miura; Seiichi Ishizuka; Hiroaki Takayama; Atsushi Kittaka

doi:10.1039/B311107E

Remarkable effect of 2α-modification on the VDR antagonistic activity of 1α-hydroxyvitamin D₃-26,23-lactones

Nozomi Saito,^a Toshihiro Matsunaga,^a Toshie Fujishima,^a Miyuki Anzai,^b Hiroshi Saito,^b Kazuya Takenouchi,^b Daishiro Miura,^b Seiichi Ishizuka,^b Hiroaki Takayama^a and Atsushi Kittaka*^a

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^a Faculty of Pharmaceutical Sciences, Teikyo University, Kanagawa 199-0195, Japan
E-mail: akittaka@pharm.teikyo-u.ac.jp
Fax: +81-426-85-3714
Tel: +81-426-85-3715

^b Teijin Institute for Bio-Medical Research, Tokyo 191-8512, Japan
Fax: +81-42-586-8298
Tel: +81-42-586-8220

Abstract

Novel 2α-methyl-, 2α-(3-hydroxypropyl)- and 2α-(3-hydroxypropoxy)-substituted 25-dehydro-1α-hydroxyvitamin D₃-26,23-lactone derivatives were efficiently synthesized via Reformatsky type allylation and palladium-catalyzed alkenylative cyclization processes, and their biological activities were evaluated. Introducing functional groups into the 2α-position of the vitamin D₃-26,23-lactones resulted in remarkable enhancement of their antagonistic activity on vitamin D receptor (VDR).

Organic & Biomolecular Chemistry

Remarkable effect of 2α-modification on the VDR antagonistic activity of 1α-hydroxyvitamin D₃-26,23-lactones

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Remarkable effect of 2α-modification on the VDR antagonistic activity of 1α-hydroxyvitamin D₃-26,23-lactones

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