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Acyl and Benzyl‐ C‐ β ‐D‐ Glucosides: Synthesis and Biostudies for Glucose‐Uptake‐Promoting Activity in C2C12 Mytotubes
Author(s) -
Reddy Mannem Rajeswara,
Hemaiswarya Shanmugam,
Kommidi Harikrishna,
Aidhen Indrapal Singh,
Doble Mukesh
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901037
Subject(s) - chemistry , c2c12 , amide , glut4 , d glucose , stereochemistry , biochemistry , in vitro , myogenesis , gene , chromosomal translocation
A convenient and scalable synthetic approach has been developed for the synthesis of acyl‐ C ‐β‐ d ‐glucosides and benzyl‐ C ‐β‐ d ‐glucosides. The use of Weinreb‐amide (WA) functionality was crucial for this accomplishment as the other apparently capable alternatives, had severe limitations for the access to acyl‐ C ‐glucosides. The synthesized compounds, acyl and benzyl‐ C ‐glucosides promote glucose‐uptake activity in the C2C12 (mouse skeletal muscle) cell lines through PPAR‐γ mediated GLUT4 expression. The developed synthetic scheme for acyl‐and benzyl‐C‐ β ‐ d ‐glucosides and biostudies evaluating their activity as glucose‐uptake promoters are disclosed herein.