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Stereo- And regioselective hydroboration of 1-exo-methylene pyranoses : Discovery of aryltriazolylmethyl C-galactopyranosides as selective galectin-1 inhibitors

Dahlqvist, Alexander LU ; Furevi, Axel ; Warlin, Niklas LU ; Leffler, Hakon LU and Nilsson, Ulf J. LU (2019) In Beilstein Journal of Organic Chemistry 15. p.1046-1060
Abstract

Galectins are carbohydrate recognition proteins that bind carbohydrates containing galactose and are involved in cell signaling and cellular interactions, involving them in several diseases. We present the synthesis of (aryltriazolyl)methyl galactopyranoside galectin inhibitors using a highly diastereoselective hydroboration of C1-exo-methylene pyranosides giving inhibitors with fourfold or better selectivity for galectin-1 over galectin-3, -4C (C-terminal CRD), -4N (N-terminal CRD), -7, -8C, -8N, -9C, and -9N and dissociation constants down to 170 μM.

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author
; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
C-galactoside, Galectin-1, Hydroboration, Inhibition, Selective, Triazole
in
Beilstein Journal of Organic Chemistry
volume
15
pages
15 pages
publisher
Beilstein-Institut Zur Forderung der Chemischen Wissenschaften
external identifiers
  • scopus:85066489921
  • pmid:31164942
ISSN
1860-5397
DOI
10.3762/bjoc.15.102
language
English
LU publication?
yes
id
6757a3ae-25d5-477e-892e-bff9cce5f079
date added to LUP
2019-06-19 14:07:08
date last changed
2024-05-28 16:42:31
@article{6757a3ae-25d5-477e-892e-bff9cce5f079,
  abstract     = {{<p>Galectins are carbohydrate recognition proteins that bind carbohydrates containing galactose and are involved in cell signaling and cellular interactions, involving them in several diseases. We present the synthesis of (aryltriazolyl)methyl galactopyranoside galectin inhibitors using a highly diastereoselective hydroboration of C1-exo-methylene pyranosides giving inhibitors with fourfold or better selectivity for galectin-1 over galectin-3, -4C (C-terminal CRD), -4N (N-terminal CRD), -7, -8C, -8N, -9C, and -9N and dissociation constants down to 170 μM.</p>}},
  author       = {{Dahlqvist, Alexander and Furevi, Axel and Warlin, Niklas and Leffler, Hakon and Nilsson, Ulf J.}},
  issn         = {{1860-5397}},
  keywords     = {{C-galactoside; Galectin-1; Hydroboration; Inhibition; Selective; Triazole}},
  language     = {{eng}},
  pages        = {{1046--1060}},
  publisher    = {{Beilstein-Institut Zur Forderung der Chemischen Wissenschaften}},
  series       = {{Beilstein Journal of Organic Chemistry}},
  title        = {{Stereo- And regioselective hydroboration of 1-exo-methylene pyranoses : Discovery of aryltriazolylmethyl C-galactopyranosides as selective galectin-1 inhibitors}},
  url          = {{http://dx.doi.org/10.3762/bjoc.15.102}},
  doi          = {{10.3762/bjoc.15.102}},
  volume       = {{15}},
  year         = {{2019}},
}