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

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Author

  • Magnus Berglund
  • Maria Dalence
  • Staffan Skogvall
  • Olov Sterner

Summary, in 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.

Publishing year

2008

Language

English

Pages

2513-2528

Publication/Series

Bioorganic & Medicinal Chemistry

Volume

16

Issue

5

Document type

Journal article

Publisher

Elsevier

Topic

  • Organic Chemistry

Status

Published

ISBN/ISSN/Other

  • ISSN: 0968-0896