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Synthesis of New Schiff Base of 1,3-Oxazine and 1,3-Thiazine Derivatives Derived from 4-Phenyl Substituted Chalcones and Evaluation of their Antibacterial Activity
Corresponding Author(s) : Har Lal Singh
Asian Journal of Chemistry,
Vol. 33 No. 3 (2021): Vol 33 Issue 3
Abstract
Oxazine and thiazine heterocycles have distinctive interests due to their important class of natural and non-natural products and exhibit high biological activities in the pharmaceutical and biological fields. This work was planned to synthesize Schiff base of 1,3-oxazine and 1,3-thiazine derivative from 4-phenyl substituted chalcones. The structures of the newly synthesized targeted compounds were established from UV, IR, 1H NMR, 13C NMR and DFT calculations. The molecular properties HOMO-LUMO energy, energy gap, softness and harness were calculated using DFT/B3LYP/6-311G (d,p) basis set. in vitro Antibacterial activities of Schiff bases of 1,3-oxazines and 1,3-thiazines derivatives were investigated against Gram-positive (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli) and compared with each other. It was found that thiazine derivatives showed higher activity.
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References
H. ur Rashid, Y. Xu, N. Ahmad, Y. Muhammad and L. Wang, Bioorg. Chem., 87, 335 (2019); https://doi.org/10.1016/j.bioorg.2019.03.033
S.L. Gaonkar and U.N. Vignesh, Res. Chem. Intermed., 43, 6043 (2017); https://doi.org/10.1007/s11164-017-2977-5
V.R. Suma, R. Sreenivasulu, M.V.B. Rao, M. Subramanyam, M.J. Ahsan, R. Alluri and K.R.M. Rao, Med. Chem.Res., 29, 1643 (2020); https://doi.org/10.1007/s00044-020-02590-9
V. Sharma, Y. Kumar and P. Kumar, Anticancer. Agents Med. Chem., 13, 422 (2013).
M. Asif and M. Imran, Int. J. New Chem., 7, 60 (2020); https://doi.org/10.22034/ijnc.2020.116058.1061
A.K. Srivastava and L.K. Pandey, Curr. Bioact. Compd., 15, 665 (2020); https://doi.org/10.2174/1573407214666180911130110
D.S. Zinad, A. Mahal, R.K. Mohapatra, A.K. Sarangi and M.R.F. Pratama, Chem. Biol. Drug Des., 95, 16 (2020);https://doi.org/10.1111/cbdd.13633
S.L. Gaonkar, V.U. Nagaraj and S. Nayak, Mini Rev. Org. Chem., 16, 43 (2018); https://doi.org/10.2174/1570193X15666180531092843
Y. Ünver, M. Tuluk, N. Kahriman, M. Emirik, E. Bektas and S. Direkel, Russ. J. Gen. Chem., 89, 794 (2019);https://doi.org/10.1134/S107036321904025X
R. Gawali, J. Trivedi, S. Bhansali, R. Bhosale, D. Sarkar and D. Mitra, Eur. J. Med. Chem., 157, 310 (2018);https://doi.org/10.1016/j.ejmech.2018.07.067
F.S. Gungor, B. Bati and B. Kiskan, Eur. Polym. J., 121, 109352 (2019); https://doi.org/10.1016/j.eurpolymj.2019.109352
G. Kaya, B. Kiskan and Y. Yagci, Macromolecules, 51, 1688 (2018); https://doi.org/10.1021/acs.macromol.8b00218
R. Nagamallu, P. Gurunanjappa and A.K. Kariyappa, Pharm. Chem. J., 51, 582 (2017); https://doi.org/10.1007/s11094-017-1657-5
M.J. Frisch, et al., Gaussian 03W, Revision C.01, Gaussian, Inc.,Wallingford, CT, USA (2004).
R.D. Dennington, T.A. Keith and J.M. Millam, Gauss View 5.0.8, Gaussian Inc., Wallingford, CT, USA (2004).
A.D. Becke, J. Chem. Phys., 98, 5648 (1993); https://doi.org/10.1063/1.464913
H.L. Singh and J.B. Singh, J. Assoc. Arab Univ. Basic Appl. Sci., 23, 1 (2017); https://doi.org/10.1016/j.jaubas.2016.05.003
H.L. Singh and J.B. Singh, Bioinorg. Chem. Appl., 2014, 716578 (2014); https://doi.org/10.1155/2014/716578
H.L. Singh, Phosphorus Sulfur Silicon Rel. Elem., 184, 1768 (2009); https://doi.org/10.1080/10426500802340236
M. Karabacak, Z. Cinar and M. Cinar, Spectrochim. Acta A Mol. Biomol. Spectrosc., 79, 1511 (2011);https://doi.org/10.1016/j.saa.2011.05.008
P.K. Chattaraj, B. Maiti and U. Sarkar, J. Phys. Chem. A, 107, 4973 (2003); https://doi.org/10.1021/jp034707u
E. Kavitha, N. Sundaraganesan and S. Sebastin, Indian J. Pure Appl. Phys., 48, 20 (2010)