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Synthesis, structural chemistry and antimicrobial activity of −(−) borneol derivative

  • Research Article
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Central European Journal of Chemistry

An Erratum to this article was published on 19 January 2011

An Erratum to this article was published on 19 January 2011

Abstract

Borneol is a monoterpene that is a part of traditional Chinese and Japanese medicine. (−) borneol reacted with methanesulfonyl chloride in THF/pyridine to afford the new 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methane sulfonate derivative in excellent yield. The product is characterized by H1NMR, C13NMR, mass spectroscopy as well as elemental analysis and its structure was identified by X-ray single crystal diffraction. The packing of 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methanesulfonate exhibits the non-classical C-H···O hydrogen bonding in C(4) and R2 2(8) chain and ring motifs as structural determinants. This was also confirmed by the analysis of Hirshfeld surfaces. The 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methane sulfonate antimicrobial activity was tested and compared with its parent (−) borneol against three different pathogens. Particularly, 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methane sulfonate showed high sensitivity, compared to Chloramphenicol reference material, against Escherichia coli.

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Authors and Affiliations

  1. Department of Chemistry, King Saud University, P. O. Box 2455, Riyadh, 11451, Saudi Arabia

    Khalid A. Al-Farhan, Ismail Warad, Saud I. Al-Resayes & Mohamed Ghazzali

  2. Strategic center for diabetic research, King Saud University, P.O. Box 245, Riyadh, 11411, Saudi Arabia

    Moustafa M. Fouda

Authors
  1. Khalid A. Al-Farhan
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  2. Ismail Warad
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  3. Saud I. Al-Resayes
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  4. Moustafa M. Fouda
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  5. Mohamed Ghazzali
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Correspondence to Mohamed Ghazzali.

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An erratum to this article can be found at http://dx.doi.org/10.2478/s11532-010-0147-3

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Al-Farhan, K.A., Warad, I., Al-Resayes, S.I. et al. Synthesis, structural chemistry and antimicrobial activity of −(−) borneol derivative. cent.eur.j.chem. 8, 1127–1133 (2010). https://doi.org/10.2478/s11532-010-1093-0

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  • DOI: https://doi.org/10.2478/s11532-010-1093-0

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