کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5281919 1385681 2008 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Original loading and Suzuki conditions for the solid-phase synthesis of biphenyltetrazoles. Application to the first solid-phase synthesis of irbesartan
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Original loading and Suzuki conditions for the solid-phase synthesis of biphenyltetrazoles. Application to the first solid-phase synthesis of irbesartan
چکیده انگلیسی

Biphenyltetrazoles are recognized privileged structures. Among them, the therapeutically important class of sartans displays antagonistic activity on AT1 receptors. We have developed a method for anchoring tetrazole derivatives via the heterocycle on a hydroxylated resin using zinc triflate. New Suzuki-Miyaura cross-coupling conditions are developed for the quantitative formation of the phenyl-phenyl bond. Our straightforward synthesis scheme, starting from the conserved phenyltetrazole moiety and ending with the appending of the structurally variable moiety, is well suited to the preparation of sartans and their analogues at a laboratory scale. We thus describe here the first solid phase synthesis of irbesartan, a marketed AT1 antagonist.

An original method to anchor the tetrazole ring on a hydroxybenzyl resin, associated to new Suzuki-Miyaura cross-coupling conditions, is presented. Using this method, the solid phase synthesis of irbesartan, a biphenyltetrazole antagonist of AT1 receptors, was conducted.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 49, Issue 17, 21 April 2008, Pages 2743-2747
نویسندگان
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