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Design, Synthesis, and Antifungal Activity of New ?-Aminophosphonates.

ABSTRACT: ?-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 ?-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(?-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.

SUBMITTER: Rezaei Z 

PROVIDER: S-EPMC4412091 | biostudies-literature | 2011

REPOSITORIES: biostudies-literature

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

Rezaei Zahra Z   Khabnadideh Soghra S   Zomorodian Kamiar K   Pakshir Keyvan K   Nadali Setareh S   Mohtashami Nadia N   Faghih Mirzaei Ehsan E  

International journal of medicinal chemistry 20110926

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  ...[more]

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