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Chemical synthesis of the 17-propanamide derivatives of stereoisomeric Δ14-17α- and 17β-estradiols: potential 17β-hydroxysteroid dehydrogenase inhibitors.

Abstract：

:The 17-propanamide derivatives of diastereomeric Δ(14)-17α- and 17β-estradiols, the potential candidates of a 17β-hydroxysteroid dehydrogenase (17β-HSD) inhibitor, were synthesized in 11 steps from estrone. The principal reactions employed involved in (1) conversion of estrone to the corresponding Δ(14)-estrone, (2) Grignard reaction of Δ(14)-estrone with allylmagnesium bromide followed by regioselective hydroboration of the resulting stereoisomeric 17ξ-allyl-Δ(14)-17ξ-ols with 9-borabicyclo[3.3.1]nonane (9-BBN), and (3) direct amidation of the 17ξ-O-/17ξ-C-spiro-γ-lactones with NH(3) under positive pressure of H(2).

journal_name

Chem Phys Lipids

journal_title

Chemistry and physics of lipids

authors

Iida T,Ogawa S,Tamegai H,Adachi Y,Saito H,Ikegawa S,Konishi H,Takagi A,Matsuzaki T

doi

10.1016/j.chemphyslip.2010.11.005

subject

Has Abstract

pub_date

2011-02-01 00:00:00

pages

106-12

issue

2

eissn

0009-3084

issn

1873-2941

pii

S0009-3084(10)00374-9

journal_volume

164

pub_type

杂志文章

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