当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > Synthesis of 16-(bromoalkyl)-estradiols having inhibitory effect on human placental estradiol 17 beta-hydroxysteroid dehydrogenase (17 beta-HSD type 1).

Synthesis of 16-(bromoalkyl)-estradiols having inhibitory effect on human placental estradiol 17 beta-hydroxysteroid dehydrogenase (17 beta-HSD type 1).

Abstract：

:The activity of 17 beta-HSD type 1, the enzyme that converts estrone into its more potent metabolite estradiol, has been demonstrated in all classical steroidogenic tissues and almost all peripheral tissues from both rat and human. Since 17 beta-HSD is one of the most important enzymes involved in active steroid hormone formation, its inactivation could be a clinical approach to the treatment of hormono-dependent diseases like breast cancer. Herein we report the synthesis of 16-(bromoalkyl)-estradiols and their potency to inhibit the human placenta cytosolic estradiol 17 beta-HSD (type 1). Synthetic analogues possess various side chain lengths and orientation (alpha or beta) at position 16 of the steroidal D ring. The most potent inhibitory effect was observed when the length of the side chain was 3 or 4 carbons. However, the 16 beta-(bromopropyl)-estradiol easily undergoes cyclization and its effect on 17 beta-HSD is lost. Consequently, 16 alpha-(bromopropyl)-E2, 16 alpha-(bromobutyl)-E2, and 16 beta-(bromobutyl)-E2 were the best inhibitors discussed in this paper.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Tremblay MR,Auger S,Poirier D

doi

10.1016/0968-0896(95)00041-e

subject

Has Abstract

pub_date

1995-05-01 00:00:00

pages

505-23

issue

5

eissn

0968-0896

issn

1464-3391

pii

096808969500041E

journal_volume

3

pub_type

杂志文章

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