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SAR studies of capsazepinoid bronchodilators. Part 2: Chlorination and catechol replacement in the A-ring.

Author:
  • Magnus Berglund
  • Maria Dalence
  • Staffan Skogvall
  • Olov Sterner
Publishing year: 2008
Language: English
Pages: 2513-2528
Publication/Series: Bioorganic & Medicinal Chemistry
Volume: 16
Issue: 5
Document type: Journal article
Publisher: Elsevier

Abstract english

Capsazepine as well as its derivatives and analogues are general inhibitors of constriction of human small airways. From a systematic variation of the capsazepine structure, divided into four regions, SARs were established. This paper concerns the chlorination of the A-ring as well as the replacement of the catechol with bioisosteric groups. It is revealed that chlorination of the A-ring has a profound effect on activity. Moreover, di-chlorination of the 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline structure results in a 10-fold increase in potency compared to capsazepine.

Keywords

  • Organic Chemistry

Other

Published
  • ISSN: 0968-0896
Olov Sterner
E-mail: olov.sterner [at] science.lu.se

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