Acyl and Benzyl‐ C‐ β ‐D‐ Glucosides: Synthesis and Biostudies for Glucose‐Uptake‐Promoting Activity in C2C12 Mytotubes | Zendy

Reddy Mannem Rajeswara | Zendy; Hemaiswarya Shanmugam | Zendy; Kommidi Harikrishna | Zendy; Aidhen Indrapal Singh | Zendy; Doble Mukesh | Zendy

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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.

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