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Eco-friendly synthesis, physicochemical studies, biological assay and molecular docking of steroidal oxime-ethers
The aim of this study was to report the synthesis of biologically active compounds; 7-(2′-aminoethoxyimino)-cholest-5-ene (4), a steroidal oxime-ether and its derivatives (5, 6) via a facile microwave assisted solvent free reaction methodology. This new synthetic, eco-friendly, sustainable protocol...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Leibniz Research Centre for Working Environment and Human Factors
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4908662/ https://www.ncbi.nlm.nih.gov/pubmed/27330525 http://dx.doi.org/10.17179/excli2014-675 |
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author | Alam, Mahboob Lee, Dong-Ung |
author_facet | Alam, Mahboob Lee, Dong-Ung |
author_sort | Alam, Mahboob |
collection | PubMed |
description | The aim of this study was to report the synthesis of biologically active compounds; 7-(2′-aminoethoxyimino)-cholest-5-ene (4), a steroidal oxime-ether and its derivatives (5, 6) via a facile microwave assisted solvent free reaction methodology. This new synthetic, eco-friendly, sustainable protocol resulted in a remarkable improvement in the synthetic efficiency (85-93 % yield) and high purity using basic alumina. The synthesized compounds were screened for their antibacterial against six bacterial strains by disc diffusion method and antioxidant potential by DPPH assay. The binding capabilities of a compound 6 exhibiting good antibacterial potential were assessed on the basis of molecular docking studies and four types of three-dimensional molecular field descriptors. Moreover the structure-antimicrobial activity relationships were studied using some physicochemical and quantum-chemical parameters with GAMESS interface as well as WebMO Job Manager by using the basic level of theory. Hence, this synthetic approach is believed to provide a better scope for the synthesis of steroidal oxime-ether analogues and will be a more practical alternative to the presently existing procedures. Moreover, detailed in silico docking studies suggested the plausible mechanism of steroidal oxime-ethers as effective antimicrobial agents. |
format | Online Article Text |
id | pubmed-4908662 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | Leibniz Research Centre for Working Environment and Human Factors |
record_format | MEDLINE/PubMed |
spelling | pubmed-49086622016-06-17 Eco-friendly synthesis, physicochemical studies, biological assay and molecular docking of steroidal oxime-ethers Alam, Mahboob Lee, Dong-Ung EXCLI J Original Article The aim of this study was to report the synthesis of biologically active compounds; 7-(2′-aminoethoxyimino)-cholest-5-ene (4), a steroidal oxime-ether and its derivatives (5, 6) via a facile microwave assisted solvent free reaction methodology. This new synthetic, eco-friendly, sustainable protocol resulted in a remarkable improvement in the synthetic efficiency (85-93 % yield) and high purity using basic alumina. The synthesized compounds were screened for their antibacterial against six bacterial strains by disc diffusion method and antioxidant potential by DPPH assay. The binding capabilities of a compound 6 exhibiting good antibacterial potential were assessed on the basis of molecular docking studies and four types of three-dimensional molecular field descriptors. Moreover the structure-antimicrobial activity relationships were studied using some physicochemical and quantum-chemical parameters with GAMESS interface as well as WebMO Job Manager by using the basic level of theory. Hence, this synthetic approach is believed to provide a better scope for the synthesis of steroidal oxime-ether analogues and will be a more practical alternative to the presently existing procedures. Moreover, detailed in silico docking studies suggested the plausible mechanism of steroidal oxime-ethers as effective antimicrobial agents. Leibniz Research Centre for Working Environment and Human Factors 2015-03-02 /pmc/articles/PMC4908662/ /pubmed/27330525 http://dx.doi.org/10.17179/excli2014-675 Text en Copyright © 2015 Alam et al. http://creativecommons.org/licenses/by/4.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution Licence (http://creativecommons.org/licenses/by/4.0/) You are free to copy, distribute and transmit the work, provided the original author and source are credited. |
spellingShingle | Original Article Alam, Mahboob Lee, Dong-Ung Eco-friendly synthesis, physicochemical studies, biological assay and molecular docking of steroidal oxime-ethers |
title | Eco-friendly synthesis, physicochemical studies, biological assay and molecular docking of steroidal oxime-ethers |
title_full | Eco-friendly synthesis, physicochemical studies, biological assay and molecular docking of steroidal oxime-ethers |
title_fullStr | Eco-friendly synthesis, physicochemical studies, biological assay and molecular docking of steroidal oxime-ethers |
title_full_unstemmed | Eco-friendly synthesis, physicochemical studies, biological assay and molecular docking of steroidal oxime-ethers |
title_short | Eco-friendly synthesis, physicochemical studies, biological assay and molecular docking of steroidal oxime-ethers |
title_sort | eco-friendly synthesis, physicochemical studies, biological assay and molecular docking of steroidal oxime-ethers |
topic | Original Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4908662/ https://www.ncbi.nlm.nih.gov/pubmed/27330525 http://dx.doi.org/10.17179/excli2014-675 |
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