Synthesis, spectroscopic investigations (X-ray, NMR and TD-DFT), antimicrobial activity and molecular docking of 2,6-bis(hydroxy(phenyl)methyl)cyclohexanone

Assem Barakat; Hazem A Ghabbour; Abdullah Mohammed Al-Majid; Saied M Soliman; M Ali; Yahia Nasser Mabkhot; Mohammed Rafi Shaik; Hoong-Kun Fun

doi:10.3390/molecules200713240

Synthesis, spectroscopic investigations (X-ray, NMR and TD-DFT), antimicrobial activity and molecular docking of 2,6-bis(hydroxy(phenyl)methyl)cyclohexanone

Molecules. 2015 Jul 21;20(7):13240-63. doi: 10.3390/molecules200713240.

Authors

Assem Barakat^{1

2}, Hazem A Ghabbour³, Abdullah Mohammed Al-Majid⁴, Saied M Soliman^{5

6}, M Ali⁷, Yahia Nasser Mabkhot⁸, Mohammed Rafi Shaik⁹, Hoong-Kun Fun^{10

11}

Affiliations

¹ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh-11451, Saudi Arabia. ambarakat@ksu.edu.sa.
² Department of Chemistry, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, Alexandria 21321, Egypt. ambarakat@ksu.edu.sa.
³ Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia. ghabbourh@yahoo.com.
⁴ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh-11451, Saudi Arabia.
⁵ Department of Chemistry, Rabigh College of Science and Art, King Abdulaziz University, P. O. Box 344, Rabigh 21911, Saudi Arabia. saied1soliman@yahoo.com.
⁶ Department of Chemistry, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, Alexandria 21321, Egypt. saied1soliman@yahoo.com.
⁷ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh-11451, Saudi Arabia. mohamedali.eg25@gmail.com.
⁸ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh-11451, Saudi Arabia. yahia@ksu.edu.sa.
⁹ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh-11451, Saudi Arabia. mshaik@ksu.edu.sa.
¹⁰ Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia. hfun.c@ksu.edu.sa.
¹¹ Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia. hfun.c@ksu.edu.sa.

Abstract

The synthesis of 2,6-bis(hydroxy(phenyl)methyl)cyclohexanone 1 is described. The molecular structure of the title compound 1 was confirmed by NMR, FT-IR, MS, CHN microanalysis, and X-ray crystallography. The molecular structure was also investigated by a set of computational studies and found to be in good agreement with the experimental data obtained from the various spectrophotometric techniques. The antimicrobial activity and molecular docking of the synthesized compound was investigated.

Keywords: Aldol product; DFT; TGA; X-ray; antimicrobial activity; cyclohexanone; molecular docking.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents* / chemical synthesis
Anti-Bacterial Agents* / chemistry
Anti-Bacterial Agents* / pharmacology
Antifungal Agents* / chemical synthesis
Antifungal Agents* / chemistry
Antifungal Agents* / pharmacology
Bacteria / growth & development*
Bacterial Proteins / chemistry*
Cyclohexanones* / chemical synthesis
Cyclohexanones* / chemistry
Cyclohexanones* / pharmacology
Fungal Proteins / chemistry*
Fungi / growth & development*
Molecular Docking Simulation*

Substances

Anti-Bacterial Agents
Antifungal Agents
Bacterial Proteins
Cyclohexanones
Fungal Proteins