Synthesis and DFT Study of Newly Schiff Base and Fused Heterocyclic Compounds as Antibacterial Agent
DOI:
https://doi.org/10.24297/jac.v16i0.8499Keywords:
Oxirane, Pyrazole, Isooxazole, Schiff Base, Imidazole, TriazineAbstract
Treatment of 2,3-di-(4-chlorophenyl) oxirane-2,3-dicarbonitriles(1) with nitrogen nucleophiles, e.g. N2H4, NH2OH afforded pyrazole 2, 1.2oxazole 3 derivatives respectively The 3-amino pyrazole-4-one derivatives 2 can be used as a key starting materials to synthesize some important Schiff base 4 and fused heterocyclic compounds e.g. Imidazolo-[4,5-c]pyrazole 5, Pyrazolo[3,4-e]1,2,4-triazine 6, pyrazol[1,2-a] 1,3,5-triazine 7, 8 and 9. The electromeric effect of the halogen atom in the aryl moieties can be controlled upon the rate of reaction and the yield of the product. The structures of synthesized new compounds were characterized by spectral data and screened for their antimicrobial activities against various bacteria and fungi strains. The heterocyclic compounds 7, 8 and 9 that contained bridgehead nitrogen gave an excellent result.
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K. Nishiyama, G. W. Griffin, K. Ishikawa, and D. M.Gibson, J. Org. Chem. 1982, 47, 2342. b) L. Zheng, X. Jun, N. Pengxian, L. Chenhui, and Y. Jingya, Tetrahedron, 2012, 68, 8880
G. Daidone, B. Maggio, S. Plescia, D. Raff, C. Musiu, C. Milia, G. Perra, and M. E.Marongiu, Eur. J. Med.chem., 1998, 33,375.
N. Singh, N. K. Sangwan, and K. S. Dhindsa, Pest manage. Sci., 2000, 56, 284.
G. Daidone, D. Raffa, F. Plescia, B. Maggio, and A. Roccaro, Arkivoc 2002, xi, 227.
O. Migliara, S. Plescia, P. Diana, V. Distefano, L. Camarda, and O. R. Dall, Arkivoc 2004, v, 44.
Bouabdallah, L.A. Barek, A. Zayed, A.Ramadani, I. Zidane, and A. Melhaoui, Natural product research, 2006, 20(11), 1024.
S. Nagaaki, J. Makoto, I. Shiho, N. Keita, T. Hiroyasu, A. Makoto, O. Osamu, I. Hisashi, G. Akira, I. Akane, K. Akio, and F. Takehiro, Bioorganic & Medicinal Chemistry Letters 2009, 19, 1670.
P. Dariusz, M. B. Andrzej, E. L. Agnieszk, J. S. Bohdan, and K. Jerzy, Acta Poloniae Pharmaceutica ñ Drug Research, 2007, 64(6) 535.
Ø. Justyna, O. Dorota, Z. Zofia, A. Ewa, and Z. Lucjusz, Acta Poloniae Pharmaceutica ñ Drug Research, 2008, 65, 229.
C. S. Prabodh, V. S. Sunil, J. Sandeep, S. Dalbir, and S. Bhojraj, Acta Poloniae Pharmaceutica ñ Drug Research, 2009, 66(1), 101.
M. Marcin, Z. Michal, T. Magdalena, and R. Stanislaw, Acta Poloniae Pharmaceutica ñ Drug Research, 2008, 65(5): 543.
M. C. Marcin, Z. Michal, A.R. Stanise, Acta Poloniae Pharmaceutica ñ Drug Research, 2008, 65(2), 241.
M. B. Alvarez, M. Palmeri, D. Davis, and J. S. Fritz, Talanta. 1987, 34, 473.
D. K. Johnson, T. B. Murphy, and W. H. Goodwin, Inorg. Chim. Acta 1982, 67, 159.
K. Shreenivasan, S. Perrier, S. Kochi, J. Mol. Catal. 1986, 36, 297.
M. H. Ali, S. E. Livingston: Coord. Chem. Rev. 1974, 13, 126.
M. Jain, S. Nehra, P. C.Trivedi, R. V. Singh, Metal-based drugs 2002, 9, 53.
M. Jain, R.V. Singh, Ind. J. Chem. Sci. 2003, 1, 17.
R.M. Patil, Acta Poloniae Pharmaceutica ñ Drug Research, 2007, 64(4), 345.
R.M. Patil, and N. V. Thakkar, Met. Org. Chem. 2000, 30, 1159.
S. A. Rizk, M. A. EL-Hashash, and M. M. Aburzeza, Egypt. J. Chem. 2011, 54(3), 299.
M. A. El-Hashash, S. A. Rizk, J Heterocyclic Chem 2017, 54, 1776.
S. A. Rizk, M.A. El-Hashash, K. K. Mostafa, Egypt, J. Chem. 2008, 51(5), 116.
S. A. Rizk, Amira A. El-Sayed, and Marwa M. Mounier, J. Heterocyclic Chem., 2017, 54, 3358.
M.E. Azab, S.A. Rizk, A. E. Amr, Molecules 2015, 20, 18201-18218.
D. N. Dhar, The Chemistry of chalcones and related compounds, Wiley-Interscience, New York, 1981, 228
J. R. Dimmock, D. W. Elias, M. A. Beazely, and N. M. Kandepu, Curr. Med. Chem. 1999, 6, 1125–1150.
G.D .Carlo, N. Mascolo, A.A. Izzo,and F. Capasso, Life Sci., 1999, 65(4), 337-353.
S. V. Kostanecki, and Tambor, J. Chem Ber., 1899, 32, 1921
R.K. Saini, A.S. Choudhary, Y.C. Joshi, and P. Joshi, E-J. Chem., 2006, 2(4), 224-227
H. Takayanagri, Y. Kitano, T. Yano, H. Umeki, and H. Hara, J. Can. Pat. Appl. 1995, 93(50),128.
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