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

Berglund, Magnus LU ; Dalence, Maria LU ; Skogvall, Staffan and Sterner, Olov LU (2008) In Bioorganic & Medicinal Chemistry 16(5). p.2513-2528
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 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.
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author
; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Bioorganic & Medicinal Chemistry
volume
16
issue
5
pages
2513 - 2528
publisher
Elsevier
external identifiers
  • pmid:18065228
  • wos:000255002400031
  • scopus:40749107989
  • pmid:18065228
ISSN
0968-0896
DOI
10.1016/j.bmc.2007.11.061
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
id
cf1ee2e1-9269-49b2-9b4d-421d017fdff9 (old id 1035537)
date added to LUP
2016-04-01 11:43:58
date last changed
2022-01-26 17:23:18
@article{cf1ee2e1-9269-49b2-9b4d-421d017fdff9,
  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 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.}},
  author       = {{Berglund, Magnus and Dalence, Maria and Skogvall, Staffan and Sterner, Olov}},
  issn         = {{0968-0896}},
  language     = {{eng}},
  number       = {{5}},
  pages        = {{2513--2528}},
  publisher    = {{Elsevier}},
  series       = {{Bioorganic & Medicinal Chemistry}},
  title        = {{SAR studies of capsazepinoid bronchodilators. Part 2: Chlorination and catechol replacement in the A-ring.}},
  url          = {{http://dx.doi.org/10.1016/j.bmc.2007.11.061}},
  doi          = {{10.1016/j.bmc.2007.11.061}},
  volume       = {{16}},
  year         = {{2008}},
}