Design, synthesis and evaluation of a novel class of glucosamine mimetic peptides containing 1,3-dioxane

Li Zeng; Guichao Xu; Pengchao Gao; Meng Zhang; Hong Li; Jianwei Zhang

doi:10.1016/j.ejmech.2015.01.062

Design, synthesis and evaluation of a novel class of glucosamine mimetic peptides containing 1,3-dioxane

Eur J Med Chem. 2015 Mar 26:93:109-20. doi: 10.1016/j.ejmech.2015.01.062. Epub 2015 Feb 2.

Authors

Li Zeng¹, Guichao Xu¹, Pengchao Gao², Meng Zhang¹, Hong Li¹, Jianwei Zhang³

Affiliations

¹ College of Pharmaceutical Sciences, Capital Medical University, Beijing 100069, PR China.
² School of Pharmacy Institute of Peking University, Beijing 100191, PR China.
³ College of Pharmaceutical Sciences, Capital Medical University, Beijing 100069, PR China. Electronic address: jwzhang2006@163.com.

PMID: 25666911
DOI: 10.1016/j.ejmech.2015.01.062

Abstract

A number of novel 2-(N-(2-(5,5-dimethyl-1,3-dioxane-2-yl)ethyl)aminoacyl)amino-2-deoxy- d-glucopyranoside were synthesized from a readily available starting material, glucosamine, 2,2-dimethyl-1,3-propanediol and 1,1,3,3-tetramethoxypropane, and evaluated for their anti-inflammatory activity. Our results showed that all of the compounds tested exhibited a significant inhibition of xylene-induced inflammation in mice.

Keywords: 1,3-Dioxane; Amino sugar; Glucosamine; Inflammation.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anti-Inflammatory Agents / chemical synthesis*
Anti-Inflammatory Agents / chemistry
Anti-Inflammatory Agents / pharmacology
Anti-Inflammatory Agents / therapeutic use
Dioxanes / chemistry*
Drug Design*
Edema / drug therapy
Glucosamine / chemistry*
Male
Mice
Mice, Inbred ICR
Molecular Structure
Peptidomimetics / chemical synthesis*
Peptidomimetics / chemistry
Peptidomimetics / pharmacology
Peptidomimetics / therapeutic use

Substances

Anti-Inflammatory Agents
Dioxanes
Peptidomimetics
Glucosamine