%0 Journal Article
%T Design, Synthesis, and Antifungal Activity of New ¦Á-Aminophosphonates
%A Zahra Rezaei
%A Soghra Khabnadideh
%A Kamiar Zomorodian
%A Keyvan Pakshir
%A Setareh Nadali
%A Nadia Mohtashami
%A Ehsan Faghih Mirzaei
%J International Journal of Medicinal Chemistry
%D 2011
%I Hindawi Publishing Corporation
%R 10.1155/2011/678101
%X ¦Á-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 ¦Á-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(¦Á-aminophosphonates) with the best negative ¦¤G in docking study showed maximum antifungal activity against Microsporum canis, and other investigated compounds did not have a good antifungal activity. 1. Introduction The ¦Á-aminophosphonates are amino acid analogues, which have found a wide range of applications in the areas of industrial, agricultural, and medicinal chemistry owing to their biological and physical properties as well as their utility as synthetic intermediates [1¨C5]. As a kind of natural amino acid analogues, ¦Á-aminophosphonates constitute an important class of compounds with diverse biological activities. The activity of ¦Á-aminophosphonates as pharmacogenic agents [6] is reported in the literature. Also it has been reported that some alkyl-substituted phosphonate compounds have antifungal activity [7, 8], antibacterial activity [9, 10], antitumor effects [11¨C13], and antiviral activity [14]. Three-component synthesis starting from aldehydes, amines and diethyl phosphite or triethyl phosphite have been reported by using Lewis and Bronsted acid catalysts such as LiClO4 [15], InCl3 [16], AlCl3 [17], lanthanide triflates/magnesium sulfate [18], SbCl3/Al2O3 [19], TaCl5-SiO2 [20], CF3CO2H [21], scandium (tris-dodecyl sulfate) [22], BF3¡¤Et2O [23], M(OTf)n £¿ £¿[24], and M(ClO4)n [25], though, many of these methods suffer from some drawbacks such as long reaction times, low yields of the products, requiring stoichiometric amounts of catalysts, costly and moisture sensitive catalysts, and use of highly toxic or toxic catalysts. More recently, ZrOCl2¡¤8H2O [26] or ZrO(ClO4)2¡¤6H2O [27] and TiO2 [28] are reported to be effective catalysts for the formation of ¦Á-aminophosphonates using a three- component system composing of aldehydes/ketones,
%U http://www.hindawi.com/journals/ijmc/2011/678101/