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SAR studies of capsazepinoid bronchodilators 3: The thiourea part (coupling region) and the 2-(4-chlorophenyl)ethyl moiety (C-region).

Author:
  • Magnus Berglund
  • Maria Dalence
  • Staffan Skogvall
  • Olov Sterner
Publishing year: 2008
Language: English
Pages: 2529-2540
Publication/Series: Bioorganic & Medicinal Chemistry
Volume: 16
Issue: 5
Document type: Journal article
Publisher: Elsevier

Abstract english

Certain derivatives and analogues of capsazepine are potent in vitro inhibitors of bronchoconstriction in human small airways. During an investigation of the dependency of the potency on the structural features of the capsazepinoids in the thiourea moiety (coupling region) and the 2-(4-chlorophenyl)ethyl moiety (C-region), it was revealed that capsazepinoids with a thiourea or an amide link between the B-ring and the C-region in general have a good bronchorelaxing activity, while urea is a less attractive choice. Further, it was shown that 1,2,3,4-tetrahydroisoquinolines with a 2-(phenyl)ethyl derivative as the C-region are considerably more potent than those with an octyl group, while 2,3,4,5-tetrahydro-1H-2-benzazepines were found to be more insensitive to the nature of the C-region.

Keywords

  • Organic Chemistry
  • Bronchodilator
  • SAR
  • 2-(Phenyl)ethyl
  • C-region
  • Thiourea
  • Capsazepine
  • Coupling region
  • Small human airways
  • Asthma
  • COPD

Other

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

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