Stereo- And regioselective hydroboration of 1-exo-methylene pyranoses : Discovery of aryltriazolylmethyl C-galactopyranosides as selective galectin-1 inhibitors
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/6757a3ae-25d5-477e-892e-bff9cce5f079
- author
- Dahlqvist, Alexander LU ; Furevi, Axel ; Warlin, Niklas LU ; Leffler, Hakon LU and Nilsson, Ulf J. LU
- organization
- publishing date
- 2019
- 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
- 2024-10-02 05:25:52
@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}}, }