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Synthesis and biological properties of 2-methylene-19-nor-25-dehydro-1alpha-hydroxyvitamin D(3)-26,23-lactones--weak agonists.

Abstract：

:In a continuing effort to explore the 2-methylene-1alpha-hydroxy-19-norvitamin D(3) class of pharmacologically important vitamin D compounds, two novel 2-methylene-19-nor-25-dehydro-1alpha-hydroxyvitamin D(3)-26,23-lactones, GC-3 and HLV, were synthesized and biologically tested. Based on reports of similarly structured molecules, it was hypothesized that these compounds might act as antagonists, at least in vitro. The pathway designed to synthesize these compounds was based on two key steps: first, the Lythgoe-type Wittig-Horner coupling of Windaus-Grundmann-type ketone 18, with phosphine oxide 15, followed, later in the synthesis, by the Zn-mediated Reformatsky-type allylation of aldehyde 20 with methylbromomethylacrylate 8. Our biological data show that neither compound has antagonistic activity but acts as weak agonists in vitro and in vivo.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Chiellini G,Grzywacz P,Plum LA,Barycki R,Clagett-Dame M,DeLuca HF

doi

10.1016/j.bmc.2008.08.011

subject

Has Abstract

pub_date

2008-09-15 00:00:00

pages

8563-73

issue

18

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(08)00727-X

journal_volume

16

pub_type

杂志文章

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