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Synthesis, Characterization and Biological Screening of Novel Metal(II) Complexes of 2-{[2-(5-Benzoyl-1H-benzotriazol-1-yl)-2-oxoethyl]amino}-5-bromobenzoic Acid
Corresponding Author(s) : P.S. Desai
Asian Journal of Chemistry,
Vol. 33 No. 4 (2021): Vol 33 Issue 4
Abstract
In this work, 5-bromoanthranilic acid was condensed with 1-(5-benzoyl-1H-1,2,3-benzotriazole-1-yl)-2-chloro-ethanone to form 2-{[2-(5-benzoyl-1H-benzotriazol-1-yl)-2-oxoethyl]amino}-5-bromobenzoic acid. The newly synthesized ligand and its metal(II) complexes with first transition metal series (Cu(II), Ni(II), Co(II), Zn(II) and Mn(II)) have been synthesized and characterized by using elemental analysis, infrared and electronic spectra. The IR spectra, NMR spectra and atomic absorption analysis show that the benzotriazole ligand formed chelates with metal in a 2:1 (ligand:metal) stochiometry. All the metal(II) complexes were screened for their antibacterial activity against Gram-positive and Gram-negative bacteria. Among the synthesized metal(II) complexes, Cu(II) complex showed the highest antibacterial activity.
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- S. Maddila, R. Pagadala and S.B. Jonnalagadda, Lett. Org. Chem., 10, 693 (2013); https://doi.org/10.2174/157017861010131126115448
- P.K. Sharma, A. Amin and M. Kumar, Open Med. Chem. J., 14, 49 (2020); https://doi.org/10.2174/1874104502014010049
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- A. Palumbo Piccionello and A. Guarcello, Curr. Bioact. Compd., 6, 266 (2010); https://doi.org/10.2174/157340710793237308
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- K.M. Pandya, P.S. Desai, N.B. Patel and B.P. Dave, Chem. Biol. Interact., 8, 314 (2018).
- P.S. Desai and D.V. Parekh, Der Chem. Sinica, 3, 722 (2012).
- P.S. Desai and D.V. Parekh, Adv. Appl. Sci. Res., 3, 1992 (2012).
- K.M. Pandya and P.S. Desai, World J. Pharm. Res., 10, 465 (2018); https://doi.org/10.20959/wjpr201810-12240
- A.I. Vogel, A Organic Practical Book, Longmans: London, ed 6, p.1274 (1989).
- S. Guru, R. Yadav, S. Srivastava, S.K. Srivastava and S.D. Srivastava,J. Indian Chem. Soc., 83, 1236 (2006).
- A.I. Vogel, A Text Book of Quantitative Inorganic Analysis, ELBS:London, ed 3 (1978).
- S. Bance, Hand Baook of Practical Microanalysis, John Wiley & Sons: New York (1988).
- J. Lewis and R.G. Wilkins, Modern Coordination Chemistry, Interscience: New York (1964).
- B.N. Figgis and J. Lewis, The Magneto Chemistry of Chelates in Modern Coordination Chemistry, Interscience: New York (1960).
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- S.N. Poddar, K. Dey, J. Haldar and S.C. Nathasarkar, J. Indian Chem. Soc., 47, 743 (1970).
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References
S. Maddila, R. Pagadala and S.B. Jonnalagadda, Lett. Org. Chem., 10, 693 (2013); https://doi.org/10.2174/157017861010131126115448
P.K. Sharma, A. Amin and M. Kumar, Open Med. Chem. J., 14, 49 (2020); https://doi.org/10.2174/1874104502014010049
I. Briguglio, S. Piras, P. Corona, E. Gavini, M. Nieddu, G. Boatto and A. Carta, Eur. J. Med. Chem., 97, 612 (2015); https://doi.org/10.1016/j.ejmech.2014.09.089
R.R. Kale, V. Prasad, P.P. Mohapatra and V.K. Tiwari, Monatsh. Chem., 141, 1159 (2010); https://doi.org/10.1007/s00706-010-0378-1
M. Vinodh, F.H. Alipour, A.A. Mohamod and T.F. Al-Azemi, Molecules, 17, 11763 (2012); https://doi.org/10.3390/molecules171011763
I. Briguglio, S. Piras, P. Corona, E. Gavini, M. Nieddu, G. Boatto and A. Carta, Eur. J. Med. Chem., 97, 612 (2015); https://doi.org/10.1016/j.ejmech.2014.09.089
L. Tian, Y. Sun, H. Li, X. Zheng, Y. Cheng, X. Liu and B. Qian, J.Inorg. Biochem., 99, 1646 (2005); https://doi.org/10.1016/j.jinorgbio.2005.05.006
B. Modzelewska-Banachiewicz, J. Banachiewicz, A. Chodkowska, E. Jagiello-Wójtowicz and L. Mazur, Eur. J. Med. Chem., 39, 873 (2004); https://doi.org/10.1016/j.ejmech.2004.07.002
D.-K. Kim, J. Kim and H.J. Park, Bioorg. Med. Chem. Lett., 14, 2401 (2004); https://doi.org/10.1016/j.bmcl.2004.03.024
Z. El-Sonbati, A.A. El-Bindary, A. El-Dissouky, T.M. El-Gogary and A.S. Hilali, Spectrochim. Acta A, Mol. Biomol. Spectrosc., 58, 1623 (2002); https://doi.org/10.1016/S1386-1425(01)00627-8
A. El-Dissouky, O. Al-Fulij and S.S. Kandil, J. Coord. Chem., 57, 605 (2004); https://doi.org/10.1080/00958970410001701026
A. El-Dissouky, O. Al-Fulij and S.S. Kandil, J. Coord. Chem., 57, 605 (2004); https://doi.org/10.1080/00958970410001701026
N.M. Shuaib, N.A. Al-Awadi, A. El-Dissouky and A.-G. Shoair, J. Coord. Chem., 59, 743 (2006); https://doi.org/10.1080/00958970500402736
A.R. Katritzky, J. Jiang and L. Urogdi, Tetrahedron Lett., 30, 3303 (1989); https://doi.org/10.1016/S0040-4039(00)99227-X
A. Palumbo Piccionello and A. Guarcello, Curr. Bioact. Compd., 6, 266 (2010); https://doi.org/10.2174/157340710793237308
B.V. Suma and N.N. Natesh, J. Chem. Pharm. Res., 3, 375 (2011).
K.M. Pandya, P.S. Desai, N.B. Patel and B.P. Dave, Chem. Biol. Interact., 8, 314 (2018).
P.S. Desai and D.V. Parekh, Der Chem. Sinica, 3, 722 (2012).
P.S. Desai and D.V. Parekh, Adv. Appl. Sci. Res., 3, 1992 (2012).
K.M. Pandya and P.S. Desai, World J. Pharm. Res., 10, 465 (2018); https://doi.org/10.20959/wjpr201810-12240
A.I. Vogel, A Organic Practical Book, Longmans: London, ed 6, p.1274 (1989).
S. Guru, R. Yadav, S. Srivastava, S.K. Srivastava and S.D. Srivastava,J. Indian Chem. Soc., 83, 1236 (2006).
A.I. Vogel, A Text Book of Quantitative Inorganic Analysis, ELBS:London, ed 3 (1978).
S. Bance, Hand Baook of Practical Microanalysis, John Wiley & Sons: New York (1988).
J. Lewis and R.G. Wilkins, Modern Coordination Chemistry, Interscience: New York (1964).
B.N. Figgis and J. Lewis, The Magneto Chemistry of Chelates in Modern Coordination Chemistry, Interscience: New York (1960).
J.O. Williams, Adv. Phys. Org. Chem., 16, 159 (1978); https://doi.org/10.1016/S0065-3160(08)60088-X
W.R. Baily and E.G. Scott, Diagnostic Microbiology, The C V Moshy Cost Lovis, p. 257 (1996).
C. Furlani and G. Morpurgo, Theor. Chim. Acta, 1, 102 (1963); https://doi.org/10.1007/BF00529392
C.K. Jørgensen, L.H. Smith, G. Hanshoff and H. Prydz, Acta Chem. Scand., 9, 1362 (1955); https://doi.org/10.3891/acta.chem.scand.09-1362
R. Pappalardo, J. Chem. Phys., 33, 613 (1960); https://doi.org/10.1063/1.1731199
J. Lewis and R.S. Wilkins, Modern Coordination Chemistry, Interscience: New York, p. 290 (1960).
S. Satpathi, H.C. Rai and B.S. Sahoo, J. Indian Chem. Soc., 52, 701 (1975).
R.H. Holm, G.W. Everett and A. Chakravorty, Prog. Inorg. Chem., 7, 83 (1966).
S.N. Poddar, K. Dey, J. Haldar and S.C. Nathasarkar, J. Indian Chem. Soc., 47, 743 (1970).
L. Sacconi, P. Paoleti and M. Ciampolini, J. Am. Chem. Soc., 85, 441 (1963); https://doi.org/10.1021/ja00887a009
L.E. Lempert, V.A. Kogan, O.A. Osipov and G.V. Nemirov, Russ. J. Inorg. Chem., 11, 506 (1966).
B. Singh and R. Singh, J. Inorg. Nucl. Chem., 34, 3449 (1972); https://doi.org/10.1016/0022-1902(72)80240-9
L.N. Mulay, Magnetic Susceptibility, John Wiley & Sons: New York, (1972).
A. Rattan, Antimicrobials in Laboratory Medicine, B.I. Churchill, Livingstone, pp 85-108 (2001).