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Vol. 34 No. 3 (2022): Vol 34 Issue 3, 2022

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Synthesis, Characterization and Biological Evaluation of Some Novel Azo-Imine Compounds

https://doi.org/10.14233/ajchem.2022.23591
K. Sunitha
Department of Chemistry and Research Centre, Pioneer Kumaraswamy College (Affiliated to Manonmaniam Sundaranar University Tirunelveli), Nagercoil-629003, India
Smitha Nair
Department of Chemistry, Sree Ayyappa College for Women, Chunkankadai-629807, India
P. Palanisamy
Department of Chemistry and Research Centre, Pioneer Kumaraswamy College (Affiliated to Manonmaniam Sundaranar University Tirunelveli), Nagercoil-629003, India

Corresponding Author(s) : K. Sunitha

sunitha.k@sreeayyappacollege.com

Asian Journal of Chemistry, Vol. 34 No. 3 (2022): Vol 34 Issue 3, 2022

Abstract

The oxidative cyclization of thiosemicarbazone (III) synthesized from reaction between substituted aryl aldehydes (I) with thiosemicarbazide (II) was done using ferric chloride as oxidative agent to get 2-amino-5-phenyl-1,3,4-thiadiazole (IV). 2-Amino-5-phenyl-1,3,4-thiadiazole was introduced in condensation reactions with substituted aldehydes to obtain benzylidene imine derivatives (VI)1-5. Further these were treated with sulphanilic acid to give new 2-{[5-phenyl-1,3,4-thiadiazole-2-imino] substituted benzene}diazenyl benzene sulfonic acid derivatives (VII)1-5. These derivatives were further characterized by FT-IR, 1H NMR and 13C NMR spectral studies and were screened for antibacterial, antifungal and antioxidant activities.

Keywords

2-Amino-5-phenyl-1 3 4-thiadiazole Benzylidene imine Sulphanilic acid Thiosemicarbazone
Sunitha, K., Nair, S., & Palanisamy, P. (2022). Synthesis, Characterization and Biological Evaluation of Some Novel Azo-Imine Compounds. Asian Journal of Chemistry, 34(3), 663–667. https://doi.org/10.14233/ajchem.2022.23591
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References
  1. A.K. Jain, S. Sharma, A. Vaidya, V. Ravichandran and R.K. Agrawal, Chem. Biol. Drug Des., 81, 557 (2013); https://doi.org/10.1111/cbdd.12125
  2. Y. Hu, C. Li, X. Wang, Y. Yang and H. Zhu, Chem. Rev., 114, 5572 (2014); https://doi.org/10.1021/cr400131u
  3. Y. Li, J. Geng, Y. Liu, S. Yu and G. Zhao, ChemMedChem, 8, 27 (2013); https://doi.org/10.1002/cmdc.201200355
  4. A. Karaburun, U.A. Cevik, D. Osmaniye, B. Saglik, B.K. Cavusoglu, S. Levent, Y. Ozkay, A. Koparal, M. Behcet and Z.A. Kaplancikli, Molecules, 23, 3129 (2018); https://doi.org/10.3390/molecules23123129
  5. M. Gür, N. Sener, Ç.A. Kastas, O.E. Özkan, H. Muglu and M.A.M. Elmaswari, J. Heterocycl. Chem., 54, 3578 (2017); https://doi.org/10.1002/jhet.2984
  6. H.N. Hafez, M.I. Hegab, I.S. Ahmed-Farag and A.B.A. El-Gazzar, Bioorg. Med. Chem., 18, 4538 (2008); https://doi.org/10.1016/j.bmcl.2008.07.042
  7. M.D. Altintop, B. Sever, A. Özdemir, S. Ilgin, Ö. Atli, G. Turan-Zitouni and Z.A. Kaplancikli, Anticancer. Agents Med. Chem., 18, 1606 (2019); https://doi.org/10.2174/1871520618666180509111351
  8. J.R. Richwine, 2,5-Dimercapto-1,3,4-thiadiazole as a Cross-Linker for Saturated Halogen Containing Polymers, U.S. Patent 4288576 (1981).
  9. L. Jin, G. Wang, X. Li and L. Li, J. Appl. Electrochem., 41, 377 (2011); https://doi.org/10.1007/s10800-010-0246-z
  10. H.R. Maradiya, J. Serb. Chem. Soc., 67, 709 (2002); https://doi.org/10.2298/JSC0211709M
  11. H. Yan, H. Su, D. Tian, F. Miao and H. Li, Sens. Actuators B Chem., 160, 656 (2011); https://doi.org/10.1016/j.snb.2011.08.044
  12. F. Hipler, R.A. Fischer and J. Muller, Phys. Chem. Chem. Phys., 7, 731 (2005); https://doi.org/10.1039/B415019H
  13. J.F. Dawson, Color. Technol., 9, 25 (1978).
  14. A. Arcoria, M.R. De Giorgi, F. Fatuzzo and M.L. Longo, Dyes Pigments, 21, 67 (1993); https://doi.org/10.1016/0143-7208(93)85005-K
  15. M.R. De Giorgi, R. Carpignano and A. Cerniani, Dyes Pigments, 37, 187 (1998); https://doi.org/10.1016/S0143-7208(97)00054-5
  16. H. Zollinger, Azo dyes and Pigments. In Color Chemistry: Syntheses, Properties, and Applications of Organic Dyes and Pigments, WileyVCH: Zurich, Switzerland, Ed.: 3, pp. 165–254 (2003).
  17. R. Ullrich and T. Grewer, Thermochim. Acta, 225, 201 (1993); https://doi.org/10.1016/0040 6031(93)80188-G
  18. R. Zhao, C. Tan, Y. Xie, C. Gao, H. Liu and Y. Jiang, Tetrahedron Lett., 52, 3805 (2011); https://doi.org/10.1016/j.tetlet.2011.05.054
  19. T.F. Chung, Y.M. Wu and C.H. Cheng, J. Org. Chem., 49, 1215 (1984); https://doi.org/10.1021/jo00181a015
  20. G.R. Srinivasa, K. Abiraj and D.C. Gowda, Synth. Commun., 33, 4221 (2003); https://doi.org/10.1081/SCC-120026850
  21. N.A. Noureldin and J.W. Bellegarde, Synthesis, 939 (1999); https://doi.org/10.1055/s-1999-3489
  22. I. Bhatnagar and M.V. George, J. Org. Chem., 33, 2407 (1968); https://doi.org/10.1021/jo01270a052
  23. H. Faustino, R.M. El-Shishtawy, L.V. Reis, P.F. Santos and P. Almeida, Tetrahedron Lett., 49, 6907 (2008); https://doi.org/10.1016/j.tetlet.2008.09.096
  24. S.M. Tambe, R.G. Tasaganva, S.R. Inamdar and M.Y. Kariduraganavar, J. Appl. Polym. Sci., 125, 1049 (2012); https://doi.org/10.1002/app.34238
  25. I.H.R. Tomi, A.H.R. Al-Daraji, R.R.T. Al-Qaysi, M.M. Hasson and K.H.D. Al-Dulaimy, Arab. J. Chem., 7, 687 (2014); https://doi.org/10.1016/j.arabjc.2010.12.003
  26. C.T. Keerthi Kumar, J. Keshavayya, T.N. Rajesh, S.K. Peethambar and A.R.S. Ali, Org. Chem. Int., 2013, 370626 (2013); https://doi.org/10.1155/2013/370626
  27. A. Kedzia, A. Kudelko, M. Swiatkowski and R. Kruszynski, Dyes Pigments, 172, 107865 (2020); https://doi.org/10.1016/j.dyepig.2019.107865
  28. M. Wróblowska, A. Kudelko, N. Kuznik, K. Laba and M. Lapkowski, J. Heterocycl. Chem., 54, 1550 (2017); https://doi.org/10.1002/jhet.2743
  29. A. Kudelko, M. Wróblowska and M. Lapkowski, Synlett, 26, 2127 (2015); https://doi.org/10.1055/s-0034-1378826
  30. A.T. Mavrova, D. Wesselinova, Y.A. Tsenov and P. Denkova, Eur. J. Med. Chem., 44, 63 (2009); https://doi.org/10.1016/j.ejmech.2008.03.006
  31. N.B. Charbe, A.P. Mehere, S.G. Shende, V.S. Mohod, D.T. Gautam, M. Madusudhan and Ch. Chaitanya, Int. J. Drug Discov., 2, 17 (2010).
  32. P.C. Kohner, J.E. Rosenblatt and F.R. Cockerill 3rd, J. Clin. Microbiol., 32, 1594 (1994); https://doi.org/10.1128/jcm.32.6.1594-1596.1994
  33. A.J.P. Assam, J.P. Dzoyem, C.A. Pieme and V.B. Penlap, BMC Complement. Altern. Med., 10, 1 (2010); https://doi.org/10.1186/1472-6882-10-40
  34. A.W. Bauer, W.M.M. Kirby, J.C. Sherris and M. Turck, Am. J. Clin. Pathol., 45, 493 (1966).
  35. B.W. Williams, M.E. Cuvelier and C. Berset, Lebensm. Wiss. Technol., 28, 25 (1995); https://doi.org/10.1016/S0023-6438(95)80008-5
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