MISC

査読有り
2003年8月

Effect of the acyl groups on O -> N acyl migration in the water-soluble Prodrugs of HIV-1 protease inhibitor

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  • Y Hamada
  • ,
  • H Matsumoto
  • ,
  • T Kimura
  • ,
  • Y Hayashi
  • ,
  • Y Kiso

13
16
開始ページ
2727
終了ページ
2730
記述言語
英語
掲載種別
DOI
10.1016/S0960-894X(03)00576-6
出版者・発行元
PERGAMON-ELSEVIER SCIENCE LTD

To improve the low water-solubility of HIV-1 protease inhibitors KNI-272, -279 and -727, we previously reported the water-soluble prodrugs of these inhibitors based on O-->N intramolecular acyl migration reaction. These prodrugs were rapidly converted to the corresponding parent drugs under physiological conditions. To understand the steric and electrostatic effects of O-acyl moiety on the migration rate, we examined several types of prodrug. A remarkably slow migration was observed in the benzoyl-type prodrugs, and Hammett plot of migration rate constants of p-substituted benzoyl-type prodrugs gave a linear free energy relationship. (C) 2003 Elsevier Ltd. All rights reserved.

Web of Science ® 被引用回数 : 32

リンク情報
DOI
https://doi.org/10.1016/S0960-894X(03)00576-6
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000184602900023&DestApp=WOS_CPL

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