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Synthesis and Characterization of Azo Schiff Bases and their β-Lactam Derivatives
Corresponding Author(s) : C.J. Patil
Asian Journal of Chemistry,
Vol. 32 No. 6 (2020): Vol 32 Issue 6
Abstract
Azo salicylaldehyde (I5) was synthesized by reaction of 5-bromo-salicylaldehyde with diazonium salt of 4-nitroaniline by diazotization method. Thus, synthesized azoaldehyde was treated with variable 2-aminobenzothiazoles (I6a-f) to synthesize the Schiff bases (I7a-f). The β-lactam derivatives (I8a-f) were also synthesized. All the newly synthesized compounds were characterized by TLC, UV-visible and FT-IR techniques.
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- B. Turan, K. Sendil, E. Sengül, M.S. Gültekin, P. Taslimi, I. Gulçin and C.T. Supuran, J. Enzym. Inhib. Med. Chem., 31(Suppl.1), 79 (2016); https://doi.org/10.3109/14756366.2016.1170014
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- H.P. Ebrahimi, J.S. Hadi, A.A. Almayah, Z. Bolandnazar, A.G. Swadi and A. Ebrahimi, Bioorg. Med. Chem., 24, 1121 (2016); https://doi.org/10.1016/j.bmc.2016.01.041
- A. Jarrahpour and M. Zarei, Molecules, 11, 49 (2006); https://doi.org/10.3390/11010049
- A.K. Bose, M.S. Manhas, J.M. van der Veen, S.S.Bari and D.R.Wagle, Tetrahedron, 48, 4831 (1992); https://doi.org/10.1016/S0040-4020(01)81577-5
- N. Mast, W. Zheng, C.D. Stout and I.A. Pikuleva, Mol. Pharmacol., 84, 86 (2013); https://doi.org/10.1124/mol.113.085902
- P.C. Sharma, A. Sinhmar, A. Sharma, H. Rajak and D.P. Pathak, J. Enzym. Inhib. Med. Chem., 28, 240 (2013); https://doi.org/10.3109/14756366.2012.720572
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- K.-F. Kong, L. Schneper and K. Mathee, APMIS, 118, 1 (2010); https://doi.org/10.1111/j.1600-0463.2009.02563.x
- S.C. Abeylath and E. Turos, Expert Opin. Drug Deliv., 5, 931 (2008); https://doi.org/10.1517/17425247.5.9.931
- M.F. Mojica, R.A. Bonomo and W. Fast, Curr. Drug Targets, 17, 1029 (2016); https://doi.org/10.2174/1389450116666151001105622
- C.M. da Silva, D.L. da Silva, L.V. Modolo, R.B. Alves, M.A. de Resende, C.V.B. Martins and Â. de Fátima, J. Adv. Res., 2, 1 (2011); https://doi.org/10.1016/j.jare.2010.05.004
- S. Samadhiya and A.K. Halve, Orient. J. Chem., 17, 199 (2001).
- T. Eicher and S. Hauptmann, The Chemistry of Heterocycles, Wiley: Weinheim (2003).
- V.M. Dembitsky, T.A. Gloriozova and V.V. Poroikov, Nat. Prod. Bioprospect., 7, 151 (2017); https://doi.org/10.1007/s13659-016-0117-3
- E. Wagner-Wysiecka, N. Lukasik, J.F. Biernat and E. Luboch, J. Incl. Phenom. Macrocycl. Chem., 90, 189 (2018); https://doi.org/10.1007/s10847-017-0779-4
- N.M. Aljamali, Biochem. Anal. Biochem., 4, 169 (2015); https://doi.org/10.4172/2161-1009.1000169
- E. Weglarz-Tomczak and L. Górecki, Chemik, 66, 1298 (2012).
- P. Przybylski, A. Huczynski, K. Pyta, B. Brzezinski and F. Bartl, Curr. Org. Chem., 13, 124 (2009); https://doi.org/10.2174/138527209787193774
- S. Slassi, A. Fix-Tailler, G. Larcher, A. Amine and A. El-Ghayoury, Heteroatom Chem., 2019, 6862170 (2019); https://doi.org/10.1155/2019/6862170
- M. Ikiz, E. Ispir, E. Aytar, M. Ulusoy, S. Karabuga, M. Aslantas and Ö. Çelik, New J. Chem., 39, 7786 (2015); https://doi.org/10.1039/C5NJ00571J
- Ö. Özdemir, Turk. J. Chem., 43, 266 (2019); https://doi.org/10.3906/kim-1807-24
References
B. Turan, K. Sendil, E. Sengül, M.S. Gültekin, P. Taslimi, I. Gulçin and C.T. Supuran, J. Enzym. Inhib. Med. Chem., 31(Suppl.1), 79 (2016); https://doi.org/10.3109/14756366.2016.1170014
T.T. Tidwell, Angew. Chem. Int. Ed., 47, 1016 (2008); https://doi.org/10.1002/anie.200702965
H.P. Ebrahimi, J.S. Hadi, A.A. Almayah, Z. Bolandnazar, A.G. Swadi and A. Ebrahimi, Bioorg. Med. Chem., 24, 1121 (2016); https://doi.org/10.1016/j.bmc.2016.01.041
A. Jarrahpour and M. Zarei, Molecules, 11, 49 (2006); https://doi.org/10.3390/11010049
A.K. Bose, M.S. Manhas, J.M. van der Veen, S.S.Bari and D.R.Wagle, Tetrahedron, 48, 4831 (1992); https://doi.org/10.1016/S0040-4020(01)81577-5
N. Mast, W. Zheng, C.D. Stout and I.A. Pikuleva, Mol. Pharmacol., 84, 86 (2013); https://doi.org/10.1124/mol.113.085902
P.C. Sharma, A. Sinhmar, A. Sharma, H. Rajak and D.P. Pathak, J. Enzym. Inhib. Med. Chem., 28, 240 (2013); https://doi.org/10.3109/14756366.2012.720572
K.C. Howard, E.K. Dennis, D.S. Watt and S. Garneau-Tsodikova, Chem. Soc. Rev., 49, 2426 (2020); https://doi.org/10.1039/C9CS00556K
K.-F. Kong, L. Schneper and K. Mathee, APMIS, 118, 1 (2010); https://doi.org/10.1111/j.1600-0463.2009.02563.x
S.C. Abeylath and E. Turos, Expert Opin. Drug Deliv., 5, 931 (2008); https://doi.org/10.1517/17425247.5.9.931
M.F. Mojica, R.A. Bonomo and W. Fast, Curr. Drug Targets, 17, 1029 (2016); https://doi.org/10.2174/1389450116666151001105622
C.M. da Silva, D.L. da Silva, L.V. Modolo, R.B. Alves, M.A. de Resende, C.V.B. Martins and Â. de Fátima, J. Adv. Res., 2, 1 (2011); https://doi.org/10.1016/j.jare.2010.05.004
S. Samadhiya and A.K. Halve, Orient. J. Chem., 17, 199 (2001).
T. Eicher and S. Hauptmann, The Chemistry of Heterocycles, Wiley: Weinheim (2003).
V.M. Dembitsky, T.A. Gloriozova and V.V. Poroikov, Nat. Prod. Bioprospect., 7, 151 (2017); https://doi.org/10.1007/s13659-016-0117-3
E. Wagner-Wysiecka, N. Lukasik, J.F. Biernat and E. Luboch, J. Incl. Phenom. Macrocycl. Chem., 90, 189 (2018); https://doi.org/10.1007/s10847-017-0779-4
N.M. Aljamali, Biochem. Anal. Biochem., 4, 169 (2015); https://doi.org/10.4172/2161-1009.1000169
E. Weglarz-Tomczak and L. Górecki, Chemik, 66, 1298 (2012).
P. Przybylski, A. Huczynski, K. Pyta, B. Brzezinski and F. Bartl, Curr. Org. Chem., 13, 124 (2009); https://doi.org/10.2174/138527209787193774
S. Slassi, A. Fix-Tailler, G. Larcher, A. Amine and A. El-Ghayoury, Heteroatom Chem., 2019, 6862170 (2019); https://doi.org/10.1155/2019/6862170
M. Ikiz, E. Ispir, E. Aytar, M. Ulusoy, S. Karabuga, M. Aslantas and Ö. Çelik, New J. Chem., 39, 7786 (2015); https://doi.org/10.1039/C5NJ00571J
Ö. Özdemir, Turk. J. Chem., 43, 266 (2019); https://doi.org/10.3906/kim-1807-24