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International Journal of Medicinal Chemistry
Volume 2011 (2011), Article ID 678101, 11 pages
http://dx.doi.org/10.1155/2011/678101
Research Article

Design, Synthesis, and Antifungal Activity of New α-Aminophosphonates

1Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz 71345, Iran
2Department of Parasitology, Faculty of Medicine, Shiraz University of Medical Sciences, Shiraz, Iran
3Department of Medicinal Chemistry, Faculty of Pharmacy, Kerman University of Medical Sciences, Kerman, Iran

Received 18 May 2011; Revised 29 June 2011; Accepted 13 July 2011

Academic Editor: Stewart Schneller

Copyright © 2011 Zahra Rezaei 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

α-Aminophosphonates are bioisosteres of amino acids and have several pharmacological activities. These compounds have been synthesized by various routes from reaction between amine, aldehyde, and phosphite compounds. In order to synthesize α-aminophosphonates, catalytic effect of CuCl2 was compared with FeCl3. Also all designed structures as well as griseofulvin were docked into the active site of microtubule (1JFF), using Autodock program. The results showed that the reactions were carried out in the presence of CuCl2 in lower yields, and also the time of reaction was longer in comparison with FeCl3. The chemical structures of the new compounds were confirmed by spectral analyses. The compounds were investigated for antifungal activity against several fungi in comparison with griseofulvin. An indole-derived bis(α-aminophosphonates) with the best negative ΔG in docking study showed maximum antifungal activity against Microsporum canis, and other investigated compounds did not have a good antifungal activity.