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Journal of Chemistry
Volume 2018, Article ID 9648710, 9 pages
https://doi.org/10.1155/2018/9648710
Research Article

Synthesis, Characterization, X-Ray Crystallography, and Antileishmanial Activities of N-Linked and O-Linked Glycopyranosides

1Department of Chemistry, Sarhad University of Science and Information Technology, Peshawar, Khyber Pakhtunkhwa, Pakistan
2Department of Chemistry, Shaheed BB University, Sheringal, Upper Dir, Khyber Pakhtunkhwa, Pakistan
3Department of Biotechnology, Quaid-I-Azam University, Islamabad 45320, Pakistan
4Department of Microbiology, Institute of Basic Medical Sciences, Khyber Medical University, Peshawar, Pakistan
5Institute of Integrative Biosciences (IIB), CECOS University of Information Technology and Emerging Sciences, Peshawar, Khyber Pakhtunkhwa, Pakistan
6H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan

Correspondence should be addressed to Sher Wali Khan; ku.oc.oohay@nhkilawrehs

Received 1 August 2017; Revised 14 November 2017; Accepted 7 December 2017; Published 30 January 2018

Academic Editor: Vinod Kumar Tiwari

Copyright © 2018 Haroon ur Rashid et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Novel -linked 5ae and -linked glycopyranosides 7ae were synthesized in high yield from commercially available L-tartaric acid containing two asymmetric centers and axis of symmetry. The compound L-tartaric acid was completely protected and then partially hydrolyzed to get the monoester, which upon treatment with different amino and hydroxyl derivatives of glycopyranoses gave the desired amides and esters. The synthesized derivatives were purified by chromatography and characterized by spectroanalytical techniques. The structure of compound 7c in the series was supported by X-ray analysis. Leishmanicidal activities of compounds 5ae and 7ae were investigated which showed moderate to good activities.