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

• Authors: Khalid Al-Farhan , Ismail Warad , Saud Al-Resayes , Moustafa Fouda , Mohamed Ghazzali
• Languages of publication: EN

Abstracts

EN

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 R22(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. [...]

Keywords

EN

(−)borneol; X-ray single crystal; Hirshfeld surfaces; C-H···O weak hydrogen bonding; Antimicrobial activity

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2010
• Volume: 8
• Issue: 5
• Pages: 1127-1133

Dates

published

1 - 10 - 2010

online

5 - 9 - 2010

Contributors

author

Khalid Al-Farhan

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

author

Ismail Warad

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

author

Saud Al-Resayes

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

author

Moustafa Fouda

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

author

Mohamed Ghazzali

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

References

• [1] J.F. King, J.R. du Manoir, Jour. Amer. Chem. Soc. 97, 9, 2566 (1975) http://dx.doi.org/10.1021/ja00842a057[Crossref]
• [2] P. Goni, P. Lopez, C. Sanchez, R. Gomez, R. Becerril, C. Nerin, Food Chem. 116, 4, 982 (2009) http://dx.doi.org/10.1016/j.foodchem.2009.03.058[Crossref]
• [3] L. Tommasi, C. Negro, A. Miceli, Anton, F. Mazzotta, J. Essential Oil Res. 21, 2, 185 (2009)
• [4] X. Liu, M. Zhao, J. Wang, W. Luo, J. Food Biochem. 33, 3, 307 (2009) http://dx.doi.org/10.1111/j.1745-4514.2009.00220.x[Crossref]
• [5] F. Romeo, S. De Luca, A. Piscopo, M. Poiana, J. Essential Oil Res. 20, 4, 373 (2008)
• [6] J. Serkedjieva, A.J. Hay, Lett. Antiviral Res. 37, 121 (1998) http://dx.doi.org/10.1016/S0166-3542(97)00067-3[Crossref]
• [7] O. Wallach, Justus Liebigs Annalen der Chemie 230, 2, 225 (1885) http://dx.doi.org/10.1002/jlac.18852300205[Crossref]
• [8] M. Armaka, E. Papanikolaou, A. Sivropoulou, M. Arsenakis Antiviral Res. 43, 79 (1999) http://dx.doi.org/10.1016/S0166-3542(99)00036-4[Crossref]
• [9] P.E. McGovern, A. Mirzoian, G.R. Hall, Proc. Nat. Acad. Sci. USA 106, 18, 7361 (2009) http://dx.doi.org/10.1073/pnas.0811578106[Crossref]
• [10] R. Grogan, F. Maresca, US patent 2009038650 (2009)
• [11] H Tan, A. Kiat, SG patent 141261 (2008)
• [12] S.P. Bhatia, C.S. Letizia, A.M. Api, Food Chem. Toxicology 46, 11S, S77 (2008) http://dx.doi.org/10.1016/j.fct.2008.06.031[Crossref]
• [13] A. Natsch, WO patent 2009000097 (2008)
• [14] Y. Konis, A. Kalay, US patent 2007224143 (2007)
• [15] T. Serena, K.S.L. Parnall, C. Knox, J. Vargo, A. Oliver, S. Merry, A. Klugh, N. Bubar, N. Anderson, L. Rieman, W. Walnoha, H. Smith, S. Rice. Adv. skin & wound care 20, 9, 485 (2007) http://dx.doi.org/10.1097/01.ASW.0000288208.85807.b8[Crossref]
• [16] N. Mirkheshti, EP patent 2014333 (2009)
• [17] S. Givaudan, S.M. Furrer, G. L. Yep, E. Flamme, WO patent 2008151460 (2008)
• [18] X. Yan, N. Wu, Z. Guo, Z. Ye, Y. Liu, US patent 2005037094 (2005)
• [19] S.P. Bhatia, D. McGinty, C.S. Letizia, A.M. Api, Food Chem.Toxicology 46, 11, S81 (2008) http://dx.doi.org/10.1016/j.fct.2008.06.054[Crossref]
• [20] Y.-H. Li, X.-P. Sun, Y.-Q. Zhang, N.-S. Wang, Amer. J. Chin. Med. 36, 4, 719 (2008) http://dx.doi.org/10.1142/S0192415X08006181[Crossref]
• [21] R.E. Granger, E.L. Campbell, G.A.R. Johnston, Biochem. Pharm. 69 1101 (2005) http://dx.doi.org/10.1016/j.bcp.2005.01.002[Crossref]
• [22] J.J.T. Chen, B.J.B. Chen, US patent 2007225364 (2007)
• [23] T. Steinbrecher, A. Hrenn, K.L. Dormann, I. Merfort, A. Labahn, Bioorg. Med. Chem. 16, 5, 2385 (2008) http://dx.doi.org/10.1016/j.bmc.2007.11.070[Crossref]
• [24] M. Czugler, E. Weber, L. Parkanyi, P.P. Korkas, P. Bombicz, Chem.-Eur.J. 9, 3741, (2003) http://dx.doi.org/10.1002/chem.200304969[Crossref]
• [25] E. Weber, P.P Korkas, M. Czugler, W. Seichter, Supramolecular Chem. 16, 3, 217 (2004) http://dx.doi.org/10.1080/10610270310001648145[Crossref]
• [26] H. Jun, L. Wenjing, J. Incl. Phenomena Macrocyclic Chem. 65, 3–4, 249 (2009)
• [27] I. Warad, M. Al-Nuri, S. Al-Resayes, K. Al-Farhan, M. Ghazzali, Acta Cryst. E65, o1597 (2009)
• [28] S. Al-Resayes, Acta Cryst. E65, o1874 (2009)
• [29] Y, Perez, S.M. -Zarcero, I. del-Hierro, I. Sierra, I.L. Solera, M. Monari, M. Fajardo, A. Otero, J. Organometallic Chem. 689, 3492 (2004) http://dx.doi.org/10.1016/j.jorganchem.2004.08.002[Crossref]
• [30] CrystalClear, Rigaku and Rigaku Americas, 9009 New Trails Dr. The Woodlands TX 77381 USA (2000–2007)
• [31] G.M. Sheldrick, Shelxtl, Acta Crystallogr. A64, 112 (2008) [Crossref]
• [32] Diamond, Version 3.1e (Crystal Impact GbR, Bonn, Germany, 2007)
• [33] S.K. Wolff, D.J. Grimwood, J.J. McKinnon, D. Jayatilaka, M.A. Spackman, CrystalExplorer, version 2.1 (University of Western Australia, Australia, 2007)
• [34] E.W. Koneman, S.D. Allen, W.M. Janda, P.C. Screckenberger, W.C. Winn, Colour Atlas and Textbook of Diagnostic Microbiology (Lippincottraven Publishers, PA, USA, 2007) 785
• [35] G.R. Desiraju, T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology (Oxford University Press, Oxford, 1999)
• [36] Z.S. Derewenda, L. Lee, U. Derewenda, J. Mol. Biol. 252, 248 (1995) http://dx.doi.org/10.1006/jmbi.1995.0492[Crossref]
• [37] M. Wahl, M. Sundaralingam, Trends Biochem. Sci. 22, 97 (1997) http://dx.doi.org/10.1016/S0968-0004(97)01004-9[Crossref]
• [38] T. Steiner, Acta Cryst. D51, 93 (1995)
• [39] G.R. Desiraju, Chem. Commun. 2995, (2005) [Crossref]
• [40] J. Bernstein, R.E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem. Int. Ed. Engl. 34, 1555 (1995) http://dx.doi.org/10.1002/anie.199515551[Crossref]
• [41] J. Grell, J. Bernstein, G. Tinhofer, Acta Cryst. B55, 1030 (1999) [Crossref]
• [42] F.A. Cotton, L.M. Daniels, G.T. Jordan IV, C.A. Murillo, Chem. Commun. 1673 (1997) [Crossref]
• [43] G.R. Desiraju, Encyclopedia of Supramolecular Chemistry (Marcel Dekker, New York, 2004) 658
• [44] T. Steiner, Angew. Chem. Int. Ed. 41, 48 (2002) http://dx.doi.org/10.1002/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO;2-U[Crossref]
• [45] T. Steiner, G.R. Desiraju, Chem. Commun. 891 (1998) [Crossref]
• [46] P. Seiler, L. Isaacs, F. Diederich, Helv. Chim. Acta 79, 1047 (1996) http://dx.doi.org/10.1002/hlca.19960790413[Crossref]
• [47] T. van Mourik, F.B. van Duijneveldt, J. Mol. Struct.: THEOCHEM 341, 63 (1995) http://dx.doi.org/10.1016/0166-1280(95)04208-N[Crossref]
• [48] X. Yan, S. Wang, M. Hodoscek, G.W.A. Milne, J. Mol. Struct.: THEOCHEM 309, 279 (1994) http://dx.doi.org/10.1016/0166-1280(94)80080-4[Crossref]
• [49] J.J. Novoa, B. Tarron, M.-H. Whangbo, J.M. Williams, J. Chem. Phys. 95, 5179 (1991) http://dx.doi.org/10.1063/1.461686[Crossref]
• [50] A. Cappelli, G. Giorgi, M. Anzini, S. Vomero, S. Ristori, C. Rossi, A. Donati, Chem. Eur. J. 10, 3177 (2004) http://dx.doi.org/10.1002/chem.200305680[Crossref]
• [51] H. Bock, R. Dieneldt, H. Schoedel, Z. Havlas, J. Chem. Soc., Chem. Commun. 1792 (1993) [Crossref]
• [52] G.R. Desiraju, J. Chem. Soc., Chem. Commun. 454 (1990) [Crossref]
• [53] L. Hirshfeld, Theor. Chim. Acta 44, 129 (1977) http://dx.doi.org/10.1007/BF00549096[Crossref]
• [54] J.J. McKinnon, D. Jayatilaka, M.A. Spackman, Chem. Commun. 3814 (2007) [Crossref]
• [55] J.J. McKinnon, M.A. Spackman, A.S. Mitchell. Acta Cryst. B60, 627 (2004) [Crossref]
• [56] A.M. Pendas, V.L. Pueyo, E. Francisco, P.M. Sanchez J. Chem. Phys. 117, 3, 1017 (2002) http://dx.doi.org/10.1063/1.1483851[Crossref]
• [57] E. Clementi, C. Roetti, At. Data Nucl. Data Tables 14, 177 (1974) http://dx.doi.org/10.1016/S0092-640X(74)80016-1[Crossref]
• [58] R.F.W. Bader, Atoms in Molecules (Oxford University Press, Oxford, 1990)

Identifiers

DOI

10.2478/s11532-010-1093-0