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SAR studies of capsazepinoid bronchodilators. Part 1: The importance of the catechol moiety and aspects of the B-ring structure.

Dalence, Maria LU ; Berglund, Magnus LU ; Skogvall, Staffan and Sterner, Olov LU (2008) In Bioorganic & Medicinal Chemistry 16(5). p.2499-2512
Abstract
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 part concerns the catechol moiety of the A-ring as well as the 2,3,4,5-tetrahydro-1H-2-azepine moiety (the B-ring) of capsazepine. It is revealed that a conformational constrain (as a fused ring) is important and that compounds with a six-membered B-ring (as a 1,2,3,4-tetrahydroisoquinoline) in general are more potent than the corresponding isoindoline, 2,3,4,5-tetrahydro-1H-2-benzazepine and 2,3,4,5-tetrahydro-1H-3-benzazepine derivatives.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Bioorganic & Medicinal Chemistry
volume
16
issue
5
pages
2499 - 2512
publisher
Elsevier
external identifiers
  • pmid:18065231
  • wos:000255002400030
  • scopus:40749142752
ISSN
0968-0896
DOI
10.1016/j.bmc.2007.11.055
language
English
LU publication?
yes
id
8227e940-bbe8-43e4-8dd2-ea3801511113 (old id 1035530)
date added to LUP
2008-03-25 14:25:22
date last changed
2017-07-30 03:35:56
@article{8227e940-bbe8-43e4-8dd2-ea3801511113,
  abstract     = {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 part concerns the catechol moiety of the A-ring as well as the 2,3,4,5-tetrahydro-1H-2-azepine moiety (the B-ring) of capsazepine. It is revealed that a conformational constrain (as a fused ring) is important and that compounds with a six-membered B-ring (as a 1,2,3,4-tetrahydroisoquinoline) in general are more potent than the corresponding isoindoline, 2,3,4,5-tetrahydro-1H-2-benzazepine and 2,3,4,5-tetrahydro-1H-3-benzazepine derivatives.},
  author       = {Dalence, Maria and Berglund, Magnus and Skogvall, Staffan and Sterner, Olov},
  issn         = {0968-0896},
  language     = {eng},
  number       = {5},
  pages        = {2499--2512},
  publisher    = {Elsevier},
  series       = {Bioorganic & Medicinal Chemistry},
  title        = {SAR studies of capsazepinoid bronchodilators. Part 1: The importance of the catechol moiety and aspects of the B-ring structure.},
  url          = {http://dx.doi.org/10.1016/j.bmc.2007.11.055},
  volume       = {16},
  year         = {2008},
}