Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2015 Jul 21;20(7):13240-63.
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

Assem Barakat  1   2 , Hazem A Ghabbour  3 , Abdullah Mohammed Al-Majid  4 , Saied M Soliman  5   6 , M Ali  7 , Yahia Nasser Mabkhot  8 , Mohammed Rafi Shaik  9 , Hoong-Kun Fun  10   11
Affiliations

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

Assem Barakat et al. Molecules. .

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.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interests.

Figures

Scheme 1
Scheme 1
Preparation of the title compound 1.
Figure 1
Figure 1
ORTEP diagram of the compound 1. Displacement ellipsoids are plotted at the 50% probability level.
Figure 2
Figure 2
ORTEP diagram of the compound 1 drawn at 50%; ellipsoids showing the chair conformation of cyclohexanone ring.
Figure 3
Figure 3
Crystal packing showing intermolecular C–H···O and N–H···O hydrogen bonds as dashed lines.
Figure 4
Figure 4
The optimized molecular structure of the studied compound (upper) and the chair form configuration of the cyclohexanone ring (lower).
Figure 4
Figure 4
The optimized molecular structure of the studied compound (upper) and the chair form configuration of the cyclohexanone ring (lower).
Figure 5
Figure 5
Comparison between the calculated and experimental geometric parameters (bond distances and angles) of the studied compounds.
Figure 6
Figure 6
Molecular Electrostatic potentials (MEP) mapped on the electron density surface calculated by the DFT/B3LYP method.
Figure 7
Figure 7
The ground state isodensity surface plots for the frontier molecular orbitals.
Figure 8
Figure 8
The calculated electronic spectra of the studied compound using the TD-DFT method.
Figure 9
Figure 9
The correlation graph between calculated and experimental 1H-NMR and 13C-NMR chemical shifts of the studied compound.
Figure 9
Figure 9
The correlation graph between calculated and experimental 1H-NMR and 13C-NMR chemical shifts of the studied compound.
Figure 10
Figure 10
The TGA curve of the studied compound.
Figure 11
Figure 11
Inhibition zone results of the synthesized compound and the references drugs.
Figure 12
Figure 12
Interaction of compound 1 with the active site of E. coli 24 kda domain.
Figure 13
Figure 13
Interaction of compound 1 with the active site of cytochrome P450 14α-sterol demethylase.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. Mahrwald R. Modern Aldol Reactions. Volumes 1–2 Wiley-VCH; Weinheim, Germany: 2004.
    1. Dimmock J.R., Kumar P., Nazarali A.J., Motaganahalli N.L., Kowalchuk T.P., Beazely M.A., Quali J.W., Oloo E.O., Allen T.M., Szydlowski J., et al. Cytotoxic 2,6-bis(arylidene)cyclohexanones and related compounds. Eur. J. Med. Chem. 2000;35:967–977. doi: 10.1016/S0223-5234(00)01173-9. - DOI - PubMed
    1. Dimmock J.R., Padmanilyam M.P., Zello G.A., Nienaber K.H., Allen T.M., Santos C.L., DeClercq E., Balzarini J., Manavathu E.K., Stables J.P. Cytotoxic analogues of 2,6-bis(arylidene)cyclohexanones. Eur. J. Med. Chem. 2003;38:169–177. doi: 10.1016/S0223-5234(02)01444-7. - DOI - PubMed
    1. Gafner S., Lee S.K., Cuendet M., Barthélémy S., Vergnes L., Labidalle S., Mehta R.G., Boone C.W., Pezzuto J.M. Biologic evaluation of curcumin and structural derivatives in cancer chemoprevention model systems. Phytochemistry. 2004;65:2849–2859. doi: 10.1016/j.phytochem.2004.08.008. - DOI - PubMed
    1. Artico M., Santo R.D., Costi R., Novellino E., Greco G., Massa S., Tramontano E., Marongiu M.E., Montis A.D., Colla P.L. Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 integrase: Synthesis, biological evaluation, and molecular modeling. J. Med. Chem. 1998;41:3948–3960. doi: 10.1021/jm9707232. - DOI - PubMed

Publication types

MeSH terms

LinkOut - more resources