Design, Synthesis, and Antifungal Activity of New α-Aminophosphonates
Author(s) -
Zahra Rezaei,
Soghra Khabnadideh,
Kamiar Zomorodian,
Keyvan Pakshir,
Setareh Nadali,
Nadia Mohtashami,
Ehsan Mirzaei
Publication year - 2011
Publication title -
international journal of medicinal chemistry
Language(s) - English
Resource type - Journals
eISSN - 2090-2069
pISSN - 2090-2077
DOI - 10.1155/2011/678101
Subject(s) - griseofulvin , antifungal , chemistry , docking (animal) , aldehyde , amine gas treating , stereochemistry , active site , catalysis , combinatorial chemistry , organic chemistry , biology , microbiology and biotechnology , medicine , nursing , pathology
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 CuCl 2 was compared with FeCl 3 . 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 CuCl 2 in lower yields, and also the time of reaction was longer in comparison with FeCl 3 . 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.
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