Issue 130, 2015

Synthesis of optically pure (S)-2-amino-5-arylpent-4-ynoic acids by Sonogashira reactions and their potential use as highly selective potent inhibitors of aldose reductase

Abstract

A new and convenient synthesis of optically pure (S)-2-amino-5-[aryl]pent-4-ynoic acids (alkynylated amino acids) is reported. (S)-2-Aminopent-4-ynoic acid-Ni-(S)-BPB was prepared and then functionalized via Sonogashira cross-coupling reactions to give (S)-2-amino-5-[aryl]pent-4-ynoic acid-Ni-(S)-BPB. The reaction conditions for the cross-coupling reaction were optimized and twelve derivatives were synthesized. Afterwards the Ni-complexes were cleaved to obtain the free (S)-2-amino-5-[aryl]pent-4-ynoic acids with excellent optical purity. The prepared (S)-2-amino-5-[aryl]pent-4-ynoic acids were tested for biological activity and selectively showed high inhibitory activity against aldose reductase (ALR2) over ALR1. Molecular docking studies have also been carried out to identify the putative binding mode of the compounds in these enzymes.

Graphical abstract: Synthesis of optically pure (S)-2-amino-5-arylpent-4-ynoic acids by Sonogashira reactions and their potential use as highly selective potent inhibitors of aldose reductase

Supplementary files

Article information

Article type
Paper
Submitted
26 Oct 2015
Accepted
10 Dec 2015
First published
14 Dec 2015

RSC Adv., 2015,5, 107400-107412

Author version available

Synthesis of optically pure (S)-2-amino-5-arylpent-4-ynoic acids by Sonogashira reactions and their potential use as highly selective potent inhibitors of aldose reductase

S. Parpart, A. Petrosyan, S. J. Ali Shah, R. A. Adewale, P. Ehlers, T. Grigoryan, A. F. Mkrtchyan, Z. Z. Mardiyan, A. J. Karapetyan, A. H. Tsaturyan, A. S. Saghyan, J. Iqbal and P. Langer, RSC Adv., 2015, 5, 107400 DOI: 10.1039/C5RA22407A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements