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

Berglund, Magnus LU ; Dalence, Maria LU ; Skogvall, Staffan and Sterner, Olov LU (2008) In Bioorganic & Medicinal Chemistry 16(5). p.2529-2540
Abstract
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)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Bronchodilator, SAR, 2-(Phenyl)ethyl, C-region, Thiourea, Capsazepine, Coupling region, Small human airways, Asthma, COPD
in
Bioorganic & Medicinal Chemistry
volume
16
issue
5
pages
2529 - 2540
publisher
Elsevier
external identifiers
  • pmid:18248995
  • wos:000255002400032
  • scopus:40749095197
ISSN
0968-0896
DOI
10.1016/j.bmc.2007.11.056
language
English
LU publication?
yes
id
a5cc4d56-d61f-473c-a91c-0178d53601d5 (old id 1042247)
date added to LUP
2008-03-25 14:10:27
date last changed
2017-07-02 03:35:27
@article{a5cc4d56-d61f-473c-a91c-0178d53601d5,
  abstract     = {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.},
  author       = {Berglund, Magnus and Dalence, Maria and Skogvall, Staffan and Sterner, Olov},
  issn         = {0968-0896},
  keyword      = {Bronchodilator,SAR,2-(Phenyl)ethyl,C-region,Thiourea,Capsazepine,Coupling region,Small human airways,Asthma,COPD},
  language     = {eng},
  number       = {5},
  pages        = {2529--2540},
  publisher    = {Elsevier},
  series       = {Bioorganic & Medicinal Chemistry},
  title        = {SAR studies of capsazepinoid bronchodilators 3: The thiourea part (coupling region) and the 2-(4-chlorophenyl)ethyl moiety (C-region).},
  url          = {http://dx.doi.org/10.1016/j.bmc.2007.11.056},
  volume       = {16},
  year         = {2008},
}