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

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 compare...

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Autores principales: Rezaei, Zahra, Khabnadideh, Soghra, Zomorodian, Kamiar, Pakshir, Keyvan, Nadali, Setareh, Mohtashami, Nadia, Faghih Mirzaei, Ehsan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Hindawi Publishing Corporation 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4412091/
https://www.ncbi.nlm.nih.gov/pubmed/25954522
http://dx.doi.org/10.1155/2011/678101
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author Rezaei, Zahra
Khabnadideh, Soghra
Zomorodian, Kamiar
Pakshir, Keyvan
Nadali, Setareh
Mohtashami, Nadia
Faghih Mirzaei, Ehsan
author_facet Rezaei, Zahra
Khabnadideh, Soghra
Zomorodian, Kamiar
Pakshir, Keyvan
Nadali, Setareh
Mohtashami, Nadia
Faghih Mirzaei, Ehsan
author_sort Rezaei, Zahra
collection PubMed
description 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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spelling pubmed-44120912015-05-07 Design, Synthesis, and Antifungal Activity of New α-Aminophosphonates Rezaei, Zahra Khabnadideh, Soghra Zomorodian, Kamiar Pakshir, Keyvan Nadali, Setareh Mohtashami, Nadia Faghih Mirzaei, Ehsan Int J Med Chem Research Article 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. Hindawi Publishing Corporation 2011 2011-09-26 /pmc/articles/PMC4412091/ /pubmed/25954522 http://dx.doi.org/10.1155/2011/678101 Text en Copyright © 2011 Zahra Rezaei et al. https://creativecommons.org/licenses/by/3.0/ 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.
spellingShingle Research Article
Rezaei, Zahra
Khabnadideh, Soghra
Zomorodian, Kamiar
Pakshir, Keyvan
Nadali, Setareh
Mohtashami, Nadia
Faghih Mirzaei, Ehsan
Design, Synthesis, and Antifungal Activity of New α-Aminophosphonates
title Design, Synthesis, and Antifungal Activity of New α-Aminophosphonates
title_full Design, Synthesis, and Antifungal Activity of New α-Aminophosphonates
title_fullStr Design, Synthesis, and Antifungal Activity of New α-Aminophosphonates
title_full_unstemmed Design, Synthesis, and Antifungal Activity of New α-Aminophosphonates
title_short Design, Synthesis, and Antifungal Activity of New α-Aminophosphonates
title_sort design, synthesis, and antifungal activity of new α-aminophosphonates
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4412091/
https://www.ncbi.nlm.nih.gov/pubmed/25954522
http://dx.doi.org/10.1155/2011/678101
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