Design and synthesis of an aminobenzo-15-crown-5-labeled estradiol tethered with disulfide linkage

被引：30

作者：

Harusawa, S ^{[1
]}

Yoshida, K ^{[1
]}

Kojima, C ^{[1
]}

Araki, L ^{[1
]}

Kurihara, T ^{[1
]}

机构：

[1] Osaka Univ Pharmaceut Sci, Osaka 5691094, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 51期

关键词：

17; beta-estradiol; labeled estradiol; 4 '-aminobenzo-15-crown-5; unsymmetrical disultides; 4-phenyl-1,2,4-triazoline-3,5-dione;

D O I：

10.1016/j.tet.2004.09.109

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel measuring method (electroimmunoassay) of 17beta-estradiol (E,) in urine or blood was proposed on the basis of a competition between E-2 and a labeled E-2 against an immobilizing antibody. To evaluate the principle, 3-{4-[17beta-hydroxy-1,3,5(10)-estratrien-3-yloxy]butyldisulfanyl}-N-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxabenzocyclopentadecen-2-yl) succinamic acid (1) was designed and synthesized as a novel aminobenzo-15-crown-5-containing E-2 tethered with disultide linkage. Two thiol-intermediates 5b and 19c were efficiently synthesized from mercaptosuccinic acid 7 and 4,4-dithiodibutyric acid 12, respectively. Formations of disulfide linkages from less reactive thiols were examined and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) could be employed for the formation of an unsymmetrical disulfide 20c from 5b and 19c. Then, removal of TMS- and allyl-protecting groups in 20c successfully afforded the crown ether-containing E-2 1. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：11911 / 11922

页数：12

共 37 条

[1]

ALLEN CFH, 1943, ORG SYNTH, V2, P580

[2]

ALLEN CFH, ORG SYNTH COLL, V3, P140

[3] Rhodium-catalyzed disulfide exchange reaction [J].