Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Crystal Structure and Antibacterial Activity of 2-(p-Tolyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole
Corresponding Author(s) : Daohang He
Asian Journal of Chemistry,
Vol. 26 No. 11 (2014): Vol 26 Issue 11
Abstract
The compound 2-(p-tolyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole (m.f. C18H18N2O4) was synthesized and characterized by 1H NMR, 13C NMR, MS and X-ray single crystal diffraction analysis. In the crystal structure, the two phenyl rings and the 1,3,4-oxadiazole ring are nearly coplanar with the dihedral angles 4.55, 1.13 and 3.97°. There is an offset face-to-face p-p stacking interaction between 1,3,4-oxadiazole ring planes. The compound molecules are connected through the offset face-to-face p-p stacking interactions to generate a three-dimensional network. The results of preliminary biological activity assay showed that the title compound exhibited good antibacterial activity against Staphylococcus aureus and Escherichia coli.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- K.K. Jha, A. Samad, Y. Kumar, M. Shaharyar, R.L. Khosa, J. Jain, V. Kumar and P. Singh, Eur. J. Med. Chem., 45, 4963 (2010); doi:10.1016/j.ejmech.2010.08.003.
- K.H. Chikhalia, D.B. Vashi and M.J. Patel, J. Enzyme Inhib. Med. Chem., 24, 617 (2009); doi:10.1080/14756360802318936.
- R.R. Somani, P.Y. Shirodkar, M.P. Toraskar and V.J. Kadam, Indian J. Pharm. Educ. Res., 42, 53 (2008).
- A. Rauf, S. Sharma and S. Gangal, Chin. Chem. Lett., 19, 5 (2008); doi:10.1016/j.cclet.2007.11.026.
- M.A. Bakht, M. Islam and A.A. Siddiqui, Indian J. Heterocycl. Chem., 15, 297 (2006).
- X.J. Zou, L.H. Lai, G.Y. Jin and Z.X. Zhang, J. Agric. Food Chem., 50, 3757 (2002); doi:10.1021/jf0201677.
- M. Amir and S. Kumar, Indian J. Heterocycl. Chem., 14, 51 (2004).
- M.S.Y. Khan and M. Akhtar, Indian J. Chem., 42B, 900 (2003).
- Z.K.A. El-Samii, J. Chem. Technol. Biotechnol., 53, 143 (1992); doi:10.1002/jctb.280530206.
- W. Shi, X.H. Qian, G.H. Song, R. Zhang and R.P. Li, J. Fluor. Chem., 106, 173 (2000); doi:10.1016/S0022-1139(00)00323-7.
- K.A. Milinkevich, C.L. Yoo, T.C. Sparks, B.A. Lorsbach and M.J. Kurth, Bioorg. Med. Chem. Lett., 19, 5796 (2009); doi:10.1016/j.bmcl.2009.07.139.
- X.M. Zheng, Z. Li, Y.L. Wang, W.D. Chen, Q.C. Huang, C.X. Liu and G.H. Song, J. Fluor. Chem., 123, 163 (2003); doi:10.1016/S0022-1139(03)00168-4.
- S. Cao, X.H. Qian, G.H. Song, B. Chai and Z.S. Jiang, J. Agric. Food Chem., 51, 152 (2003); doi:10.1021/jf0208029.
- Y.C. Zhu, D.H. He and Z.R. Yang, Spectrochim. Acta A, 72, 417 (2009); doi:10.1016/j.saa.2008.10.011.
- G.M. Sheldrick, SHELXS-97. Program for Crystal Structure Solution; University of Gottingen: Germany (1997).
- G.M. Sheldrick, SHELXL-97. Program for Crystal Structure Refinement; University of Gottingen: Germany (1997).
- X.L. Hu, X.Y. Xu, F.J. Yin and D.Q. Wang, Chin. J. Struct. Chem., 27, 733 (2008).
References
K.K. Jha, A. Samad, Y. Kumar, M. Shaharyar, R.L. Khosa, J. Jain, V. Kumar and P. Singh, Eur. J. Med. Chem., 45, 4963 (2010); doi:10.1016/j.ejmech.2010.08.003.
K.H. Chikhalia, D.B. Vashi and M.J. Patel, J. Enzyme Inhib. Med. Chem., 24, 617 (2009); doi:10.1080/14756360802318936.
R.R. Somani, P.Y. Shirodkar, M.P. Toraskar and V.J. Kadam, Indian J. Pharm. Educ. Res., 42, 53 (2008).
A. Rauf, S. Sharma and S. Gangal, Chin. Chem. Lett., 19, 5 (2008); doi:10.1016/j.cclet.2007.11.026.
M.A. Bakht, M. Islam and A.A. Siddiqui, Indian J. Heterocycl. Chem., 15, 297 (2006).
X.J. Zou, L.H. Lai, G.Y. Jin and Z.X. Zhang, J. Agric. Food Chem., 50, 3757 (2002); doi:10.1021/jf0201677.
M. Amir and S. Kumar, Indian J. Heterocycl. Chem., 14, 51 (2004).
M.S.Y. Khan and M. Akhtar, Indian J. Chem., 42B, 900 (2003).
Z.K.A. El-Samii, J. Chem. Technol. Biotechnol., 53, 143 (1992); doi:10.1002/jctb.280530206.
W. Shi, X.H. Qian, G.H. Song, R. Zhang and R.P. Li, J. Fluor. Chem., 106, 173 (2000); doi:10.1016/S0022-1139(00)00323-7.
K.A. Milinkevich, C.L. Yoo, T.C. Sparks, B.A. Lorsbach and M.J. Kurth, Bioorg. Med. Chem. Lett., 19, 5796 (2009); doi:10.1016/j.bmcl.2009.07.139.
X.M. Zheng, Z. Li, Y.L. Wang, W.D. Chen, Q.C. Huang, C.X. Liu and G.H. Song, J. Fluor. Chem., 123, 163 (2003); doi:10.1016/S0022-1139(03)00168-4.
S. Cao, X.H. Qian, G.H. Song, B. Chai and Z.S. Jiang, J. Agric. Food Chem., 51, 152 (2003); doi:10.1021/jf0208029.
Y.C. Zhu, D.H. He and Z.R. Yang, Spectrochim. Acta A, 72, 417 (2009); doi:10.1016/j.saa.2008.10.011.
G.M. Sheldrick, SHELXS-97. Program for Crystal Structure Solution; University of Gottingen: Germany (1997).
G.M. Sheldrick, SHELXL-97. Program for Crystal Structure Refinement; University of Gottingen: Germany (1997).
X.L. Hu, X.Y. Xu, F.J. Yin and D.Q. Wang, Chin. J. Struct. Chem., 27, 733 (2008).