Eco-friendly synthesis, physicochemical studies, biological assay and molecular docking of steroidal oxime-ethers

Authors

  • Mahboob Alam Division of Bioscience, Dongguk University, Gyeongju 780-714, Republic of Korea
  • Dong-Ung Lee Division of Bioscience, Dongguk University, Gyeongju 780-714, Republic of Korea

DOI:

https://doi.org/10.17179/excli2014-675

Keywords:

biological assay, physicochemical studies, microwave irradiation, steroidal oxime-ethers, molecular docking

Abstract

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.

Downloads

Published

2015-03-02

How to Cite

Alam, M., & Lee, D.-U. (2015). Eco-friendly synthesis, physicochemical studies, biological assay and molecular docking of steroidal oxime-ethers. EXCLI Journal, 14, 394–407. https://doi.org/10.17179/excli2014-675

Issue

Vol. 14 (2015)

Section

Original articles

License

Authors who publish in this journal agree to the following terms:

  • The authors keep the copyright and grant the journal the right of first publication under the terms of the Creative Commons Attribution license, CC BY 4.0. This licencse permits unrestricted use, distribution and reproduction in any medium, provided that the original work is properly cited.
  • The use of general descriptive names, trade names, trademarks, and so forth in this publication, even if not specifically identified, does not imply that these names are not protected by the relevant laws and regulations.
  • Because the advice and information in this journal are believed to be true and accurate at the time of publication, neither the authors, the editors, nor the publisher accept any legal responsibility for any errors or omissions presented in the publication. The publisher makes no guarantee, express or implied, with respect to the material contained herein.
  • The authors can enter into additional contracts for the non-exclusive distribution of the journal's published version by citing the initial publication in this journal (e.g. publishing in an institutional repository or in a book).