Biology- and Diversity-Oriented Domino Reactions for Synthesis of AMPA Receptor Antagonist IKM-159 and Analogues

Masato Oikawa; Yuuki Kasori; Lisa Katayama; Etsuko Murakami; Yuya Oikawa; Yuichi Ishikawa

doi:10.1055/s-0033-1338543

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(22): 3106-3117
DOI: 10.1055/s-0033-1338543

paper

Biology- and Diversity-Oriented Domino Reactions for Synthesis of AMPA Receptor Antagonist IKM-159 and Analogues

Authors

Masato Oikawa*

Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan Fax: +81(45)7872403 eMail: moikawa@yokohama-cu.ac.jp
Yuuki Kasori

Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan Fax: +81(45)7872403 eMail: moikawa@yokohama-cu.ac.jp
Lisa Katayama

Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan Fax: +81(45)7872403 eMail: moikawa@yokohama-cu.ac.jp
Etsuko Murakami

Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan Fax: +81(45)7872403 eMail: moikawa@yokohama-cu.ac.jp
Yuya Oikawa

Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan Fax: +81(45)7872403 eMail: moikawa@yokohama-cu.ac.jp
Yuichi Ishikawa

Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan Fax: +81(45)7872403 eMail: moikawa@yokohama-cu.ac.jp

Abstract

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Abstract

By natural product inspired diversity-oriented synthesis, we had developed a new class of selective antagonist, IKM-159, for the AMPA receptor. Here, we report syntheses of IKM-159 and skeletally diverse five analogues in racemic forms, two of which are heterotricycles and the other three compounds are truncated analogues, to study the structure–activity relationships. The key reactions are two domino reactions including Ugi/Diels–Alder reaction and domino metathesis reaction. An exceptionally high level of regiocontrol in the cross metathesis reaction is also reported.

Key words

domino reaction - heterocycles - medicinal chemistry - metathesis - multicomponent reaction

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Referenzen

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