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Synthesis, Characterization and Biological Activity of Some New Acetohydrazide Derivatives via 3,3'-Dimethylbenzidine
Corresponding Author(s) : Maysoon T. Tawfiq
Asian Journal of Chemistry,
Vol. 28 No. 4 (2016): Vol 28 Issue 4
Abstract
Schiff base (1): 2,2'-(3,3'-dimethylbiphenyl-4,4'-diyl)bis(azan-1-yl-1-ylidene)diacetic acid was obtained by condensation of 3,3'-dimethylbenzidine with glyoxalic acid in ethanol. The esterfication of 1 with ethanol in presence of sulfuric acid gave the ester (2): diphenyl-2,2'-(3,3'-dimethylbiphenyl-4,4'-diyl)bis(azan-1-yl-1-ylidene)diacetate, then converted this ester to the acid hydrazide by reaction with hydrazine hydrate in ethanol to gave (3): 2,2'-(3,3'-dimethylbiphenyl-4,4'-diyl)bis(azan-1-yl-1-ylidene)diacetohydrazide,which was reacted with substituted aldehydes in ethanol to give the corresponding Schiff bases (4 a,b,c): 2,2'-(3,3'-dimethylbiphenyl-4,4'-diyl)bis(azan-1-yl-1-ylidine)bis(N'-(3-alkyl-4-hydroxybenzylidene)acetohydrazide). The prepared compounds were characterized by spectral methods and Schiff bases were screened for antibacterial activity.
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- F. Armbruster, U. Klingebiel and M. Noltemeyer, Z. Naturforsch., 61b, 225 (2006).
- O.S. Senturk, S. Sert and U. Ozdemir, Z. Naturforsch., 58b, 1124 (2003).
- H. Mohrle and G. Keller, Z. Naturforsch., 58b, 885 (2003).
- J. Chakraborty, R.K.B. Singh, B. Samanta, C.R. Choudhury, S.K. Dey, P. Talukder, M.J. Borah and S. Mitra, Z. Naturforsch., 61b, 1209 (2006).
- C.T. Zeyrek, A. Elmali and Y. Elerman, Z. Naturforsch., 61b, 237 (2006).
- C. Janiak, P.G. Lassahn and V. Lozan, Macromol. Symp., 236, 88 (2006); doi:10.1002/masy.200690071.
- M. Mohan, M.P. Gupta, L. Chandra and N.K. Jha, Inorg. Chim. Acta, 151, 61 (1988); doi:10.1016/S0020-1693(00)83485-4.
- Z.H. Chohan and S.K.A. Sherazi, Synth. React. Inorg. Met.-Org. Chem., 29, 105 (1999); doi:10.1080/00945719909349437.
- T. Jeeworth, H.L.K. Wah, M.G. Bhowon, D. Ghoorhoo and K. Babooram, Synth. React. Inorg. Met.-Org. Chem., 30, 1023 (2000); doi:10.1080/00945710009351817.
- I.A. Tossidis, C.A. Bolos, P.N. Aslanidis and G.A. Katsoulos, Inorg. Chim. Acta, 133, 275 (1987); doi:10.1016/S0020-1693(00)87779-8.
- R.C. Aggarwal, N.K. Singh and R.P. Singh, Inorg. Chim. Acta, 20, 2794 (1981); doi:10.1021/ic50223a012.
- A. Maiti and S. Ghosh, Indian J. Chem., 29B, 980 (1989).
- J.R. Dimmock, S.C. Vashishtha and J.P. Stables, Eur. J. Med. Chem., 35, 241 (2000); doi:10.1016/S0223-5234(00)00123-9.
- N. Dharmaraj, P. Viswanathamurthi and K. Natarajan, Transition Met. Chem., 26, 105 (2001); doi:10.1023/A:1007132408648.
- C.H. Colins and P.M. Lyne, Microbial Methods, University Park Press, Baltimore, p. 422 (1970).
- L. Savini, L. Chiasserini, A. Gaeta and C. Pellerano, Bioorg. Med. Chem., 10, 2193 (2002); doi:10.1016/S0968-0896(02)00071-8.
- J.A. Anten, D. Nicholis, J.M. Markpoulos and O. Markopoulou, Polyhedron, 6, 1075 (1987); doi:10.1016/S0277-5387(00)80958-4.
- K. Andelkovic, D.Sladic, A. Bacchi, G. Pelizzi, N. Filipović and M. Rajković, Transition Met. Chem., 30, 243 (2005); doi:10.1007/s11243-004-3173-1.
- R.M. Silverstein, G.C. Bassler and T.C. Morrill, Spectrometric Identification of Organic Compounds, Wiley, New York, edn 4 (1981).
- T. Haack, R. Fattori, M. Napoletano, F. Pellacini, G. Fronza, G. Raffaini and F. Ganazzoli, Bioorg. Med. Chem., 13, 4425 (2005); doi:10.1016/j.bmc.2005.04.057.
- G. Strappaghetti, C. Brodi, G. Giannaccini and L. Betti, Bioorg. Med. Chem. Lett., 16, 2575 (2006); doi:10.1016/j.bmcl.2006.02.068.
- F. Al’-Assar, K.N. Zelenin, E.E. Lesiovskaya, I.P. Bezhan and B.A. Chakchir, Pharm. Chem., 36, 598 (2002); doi:10.1023/A:1022665331722.
- H.L. Singh and A.K. Varshney, Bioinorg. Chem. Appl., 2006, 1 (2006); doi:10.1155/BCA/2006/23245.
- R.P. Jain and J.C. Vederas, Bioorg. Med. Chem. Lett., 14, 3655 (2004); doi:10.1016/j.bmcl.2004.05.021.
- A. Scozzafava, L. Menabuoni, F. Mincione, G. Mincione and C.T. Supuran, Bioorg. Med. Chem. Lett., 11, 575 (2001); doi:10.1016/S0960-894X(00)00722-8.
- A.M. Elsome, J.M.T. Hamilton-Miller, W. Brumfitt and W.C. Noble, J. Antimicrob. Chemother., 37, 911 (1996); doi:10.1093/jac/37.5.911.
- S.K. Sahoo, R.K. Bera, M. Baral and B.K. Kanungo, J. Photochem. Photobiol. Chem., 188, 298 (2007); doi:10.1016/j.jphotochem.2006.12.027.
- H.M. Parekh and M.N. Patel, Russ. J. Coord. Chem., 32, 431 (2006); doi:10.1134/S1070328406060066.
- N. Raghav, A. Suman, M. Singh, R. Kaur and A. Rohilla, Int. J. Appl. Biol. Pharm. Technol., 2, 193 (2011).
- S.S. Li, H. Chen, S. Lei, H. Ma, R. Yu and D. Liu, Corros. Sci., 41, 1273 (1999); doi:10.1016/S0010-938X(98)00183-8.
- D. Chiarino, F. Ferrario, F. Pellacini and A. Sala, J. Heterocycl. Chem., 26, 589 (1989); doi:10.1002/jhet.5570260313.
- L. Szilagyi and Z. Gyorgydeak, J. Am. Chem. Soc., 101, 427 (1979); doi:10.1021/ja00496a026.
- W.N. Ahamed, T.G. Hassan and M.A. Abid Allah, J. Univ. Anbar Pure Sci., 4 (2010).
- L. John and L. Barry, Advanced Practical Organic Chemistry, CRC Press, edn 3 (2013).
- S. Ghammamy, R. Shakeri, B. Shaabani, K. Mehrani and S. Rajaei, Afr. J. Pure Appl. Chem., 5, 145 (2011).
- O.W. Salawu and A.O. Abdulsalam, Der Pharma Chemica, 3, 298 (2011).
- L.M. Matz and H.H. Hill Jr., Anal. Chim. Acta, 457, 235 (2002); doi:10.1016/S0003-2670(02)00021-1.
- B.S. Furnis, A.J. Hannaford, P.W. Gsmith and A.R. Tatchell, Text Book of Practical Organic Chemistry, London (2005).
- B. Mahesha, S.L. Belagali, M. Murali and K.N. Amruthesh, Int. J. Chem. Phys. Sci., 3, 82 (2010).
- R.M. Mohammed, M.Sc. Thesis, Islamic University of Gaza, Deanery of Higher Studies Faculty of Science, Gaza, Palestine (2013).
- K.J. Ibtisam, Ph.D. Thesis, Baghdad University, Baghdad, Iraq (2001)
- I.V. Arthur, Practical Organic Chemistry, edn 3, London (1973).
- W.B. Kantlehnerin, M. Trost and I. Fleming, Strategy and Efficiency in Modern Organic Chemistry, Pergamon Press, Inc., Elmsford, New York, vol. 6, pp. 485-599 (1991).
- E.K. Eurantoin and S. Patai, The Chemistry of Carboxylic Acids and Esters, Wiley Interscience, New York (1969).
- J. Hamdi, Ph.D. Thesis, Al-Mustansiria University, Baghdad, Iraq (1999).
- S. Özbey, F.B. Kaynak, H. Göker and C. Kuş, J. Chem. Crystallogr., 34, 851 (2004); doi:10.1007/s10870-004-7718-0.
- H. Abdel-Aziz, T. Elsaman, M. Attia and A. Alanazi, Molecules, 18, 2084 (2013); doi:10.3390/molecules18022084.
- D.Y. Curtin, R.C. Fuson, C.K.F. Hermann, T.C. Morrill and R.L. Shriner, The Systematic Identification of Organic Compounds, John Wiley & Sons, New York, edn 8 (2004).
- R.M. Mohareb, D.H. Fleita and O.K. Sakka, Molecules, 16, 16 (2011); doi:10.3390/molecules16010016.
- A.J. Mahrath, S.A. Aowda and S.N. Kamil, J. Babylon Univ. Pure Appl. Sci., 21, 206 (2013).
References
F. Armbruster, U. Klingebiel and M. Noltemeyer, Z. Naturforsch., 61b, 225 (2006).
O.S. Senturk, S. Sert and U. Ozdemir, Z. Naturforsch., 58b, 1124 (2003).
H. Mohrle and G. Keller, Z. Naturforsch., 58b, 885 (2003).
J. Chakraborty, R.K.B. Singh, B. Samanta, C.R. Choudhury, S.K. Dey, P. Talukder, M.J. Borah and S. Mitra, Z. Naturforsch., 61b, 1209 (2006).
C.T. Zeyrek, A. Elmali and Y. Elerman, Z. Naturforsch., 61b, 237 (2006).
C. Janiak, P.G. Lassahn and V. Lozan, Macromol. Symp., 236, 88 (2006); doi:10.1002/masy.200690071.
M. Mohan, M.P. Gupta, L. Chandra and N.K. Jha, Inorg. Chim. Acta, 151, 61 (1988); doi:10.1016/S0020-1693(00)83485-4.
Z.H. Chohan and S.K.A. Sherazi, Synth. React. Inorg. Met.-Org. Chem., 29, 105 (1999); doi:10.1080/00945719909349437.
T. Jeeworth, H.L.K. Wah, M.G. Bhowon, D. Ghoorhoo and K. Babooram, Synth. React. Inorg. Met.-Org. Chem., 30, 1023 (2000); doi:10.1080/00945710009351817.
I.A. Tossidis, C.A. Bolos, P.N. Aslanidis and G.A. Katsoulos, Inorg. Chim. Acta, 133, 275 (1987); doi:10.1016/S0020-1693(00)87779-8.
R.C. Aggarwal, N.K. Singh and R.P. Singh, Inorg. Chim. Acta, 20, 2794 (1981); doi:10.1021/ic50223a012.
A. Maiti and S. Ghosh, Indian J. Chem., 29B, 980 (1989).
J.R. Dimmock, S.C. Vashishtha and J.P. Stables, Eur. J. Med. Chem., 35, 241 (2000); doi:10.1016/S0223-5234(00)00123-9.
N. Dharmaraj, P. Viswanathamurthi and K. Natarajan, Transition Met. Chem., 26, 105 (2001); doi:10.1023/A:1007132408648.
C.H. Colins and P.M. Lyne, Microbial Methods, University Park Press, Baltimore, p. 422 (1970).
L. Savini, L. Chiasserini, A. Gaeta and C. Pellerano, Bioorg. Med. Chem., 10, 2193 (2002); doi:10.1016/S0968-0896(02)00071-8.
J.A. Anten, D. Nicholis, J.M. Markpoulos and O. Markopoulou, Polyhedron, 6, 1075 (1987); doi:10.1016/S0277-5387(00)80958-4.
K. Andelkovic, D.Sladic, A. Bacchi, G. Pelizzi, N. Filipović and M. Rajković, Transition Met. Chem., 30, 243 (2005); doi:10.1007/s11243-004-3173-1.
R.M. Silverstein, G.C. Bassler and T.C. Morrill, Spectrometric Identification of Organic Compounds, Wiley, New York, edn 4 (1981).
T. Haack, R. Fattori, M. Napoletano, F. Pellacini, G. Fronza, G. Raffaini and F. Ganazzoli, Bioorg. Med. Chem., 13, 4425 (2005); doi:10.1016/j.bmc.2005.04.057.
G. Strappaghetti, C. Brodi, G. Giannaccini and L. Betti, Bioorg. Med. Chem. Lett., 16, 2575 (2006); doi:10.1016/j.bmcl.2006.02.068.
F. Al’-Assar, K.N. Zelenin, E.E. Lesiovskaya, I.P. Bezhan and B.A. Chakchir, Pharm. Chem., 36, 598 (2002); doi:10.1023/A:1022665331722.
H.L. Singh and A.K. Varshney, Bioinorg. Chem. Appl., 2006, 1 (2006); doi:10.1155/BCA/2006/23245.
R.P. Jain and J.C. Vederas, Bioorg. Med. Chem. Lett., 14, 3655 (2004); doi:10.1016/j.bmcl.2004.05.021.
A. Scozzafava, L. Menabuoni, F. Mincione, G. Mincione and C.T. Supuran, Bioorg. Med. Chem. Lett., 11, 575 (2001); doi:10.1016/S0960-894X(00)00722-8.
A.M. Elsome, J.M.T. Hamilton-Miller, W. Brumfitt and W.C. Noble, J. Antimicrob. Chemother., 37, 911 (1996); doi:10.1093/jac/37.5.911.
S.K. Sahoo, R.K. Bera, M. Baral and B.K. Kanungo, J. Photochem. Photobiol. Chem., 188, 298 (2007); doi:10.1016/j.jphotochem.2006.12.027.
H.M. Parekh and M.N. Patel, Russ. J. Coord. Chem., 32, 431 (2006); doi:10.1134/S1070328406060066.
N. Raghav, A. Suman, M. Singh, R. Kaur and A. Rohilla, Int. J. Appl. Biol. Pharm. Technol., 2, 193 (2011).
S.S. Li, H. Chen, S. Lei, H. Ma, R. Yu and D. Liu, Corros. Sci., 41, 1273 (1999); doi:10.1016/S0010-938X(98)00183-8.
D. Chiarino, F. Ferrario, F. Pellacini and A. Sala, J. Heterocycl. Chem., 26, 589 (1989); doi:10.1002/jhet.5570260313.
L. Szilagyi and Z. Gyorgydeak, J. Am. Chem. Soc., 101, 427 (1979); doi:10.1021/ja00496a026.
W.N. Ahamed, T.G. Hassan and M.A. Abid Allah, J. Univ. Anbar Pure Sci., 4 (2010).
L. John and L. Barry, Advanced Practical Organic Chemistry, CRC Press, edn 3 (2013).
S. Ghammamy, R. Shakeri, B. Shaabani, K. Mehrani and S. Rajaei, Afr. J. Pure Appl. Chem., 5, 145 (2011).
O.W. Salawu and A.O. Abdulsalam, Der Pharma Chemica, 3, 298 (2011).
L.M. Matz and H.H. Hill Jr., Anal. Chim. Acta, 457, 235 (2002); doi:10.1016/S0003-2670(02)00021-1.
B.S. Furnis, A.J. Hannaford, P.W. Gsmith and A.R. Tatchell, Text Book of Practical Organic Chemistry, London (2005).
B. Mahesha, S.L. Belagali, M. Murali and K.N. Amruthesh, Int. J. Chem. Phys. Sci., 3, 82 (2010).
R.M. Mohammed, M.Sc. Thesis, Islamic University of Gaza, Deanery of Higher Studies Faculty of Science, Gaza, Palestine (2013).
K.J. Ibtisam, Ph.D. Thesis, Baghdad University, Baghdad, Iraq (2001)
I.V. Arthur, Practical Organic Chemistry, edn 3, London (1973).
W.B. Kantlehnerin, M. Trost and I. Fleming, Strategy and Efficiency in Modern Organic Chemistry, Pergamon Press, Inc., Elmsford, New York, vol. 6, pp. 485-599 (1991).
E.K. Eurantoin and S. Patai, The Chemistry of Carboxylic Acids and Esters, Wiley Interscience, New York (1969).
J. Hamdi, Ph.D. Thesis, Al-Mustansiria University, Baghdad, Iraq (1999).
S. Özbey, F.B. Kaynak, H. Göker and C. Kuş, J. Chem. Crystallogr., 34, 851 (2004); doi:10.1007/s10870-004-7718-0.
H. Abdel-Aziz, T. Elsaman, M. Attia and A. Alanazi, Molecules, 18, 2084 (2013); doi:10.3390/molecules18022084.
D.Y. Curtin, R.C. Fuson, C.K.F. Hermann, T.C. Morrill and R.L. Shriner, The Systematic Identification of Organic Compounds, John Wiley & Sons, New York, edn 8 (2004).
R.M. Mohareb, D.H. Fleita and O.K. Sakka, Molecules, 16, 16 (2011); doi:10.3390/molecules16010016.
A.J. Mahrath, S.A. Aowda and S.N. Kamil, J. Babylon Univ. Pure Appl. Sci., 21, 206 (2013).