Synthesis, Structural Chemistry and Antimicrobial Activity of −(−) Borneol Derivative

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Journal Title, Volume, Page: 
Central European Journal of Chemistry
Year of Publication: 
2010
Authors: 
Khalid A. Al-Farhan
Department of Chemistry, King Saud University, P. O. Box 2455, Riyadh, 11451, Saudi Arabia
Ismail Warad
Department of Chemistry, King Saud University, P. O. Box 2455, Riyadh, 11451, Saudi Arabia
Current Affiliation: 
Department of Chemistry, Faculty of Science, An-Najah National University, Nablus, Palestine
Saud I. Al-Resayes
Department of Chemistry, King Saud University, P. O. Box 2455, Riyadh, 11451, Saudi Arabia
Moustafa M. Fouda
Strategic center for diabetic research, King Saud University, P.O. Box 245, Riyadh, 11411, Saudi Arabia
Mohamed Ghazzali
Department of Chemistry, King Saud University, P. O. Box 2455, Riyadh, 11451, Saudi Arabia
Preferred Abstract (Original): 
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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