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Vol. 35 No. 11 (2023): Vol 35 Issue 11, 2023

Copyright (c) 2023 Nilesh Junghare, Pravin Kadam, Jotiram Chavan, Minakshi Patil, Gurunath Chougale

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A Highly Efficient, Catalyst-Free Synthesis of S-Alkyl/aryl Dithiocarbamate Derivatives under Green Conditions and Evaluation of their Biological Activity

https://doi.org/10.14233/ajchem.2023.28324
Nilesh Junghare
Clean Technology and Applied Materials Research Group, Department of Chemical and Metallurgical Engineering, Vaal University of Technology, Private Bag X021, South Africa
https://orcid.org/0000-0002-5450-7099
Pravin Kadam
Department of Chemistry, Khare Dhere Bhosale College, Guhagar, Ratnagiri-415703, India
https://orcid.org/0009-0006-7619-726X
Jotiram Chavan
Department of Chemistry, Shri Yashwantrao Patil Science College, Solankur, Radhanagari, Kolhapur-416212, India
https://orcid.org/0009-0002-7087-2851
Minakshi Patil
Department of Chemistry, Shri Yashwantrao Patil Science College, Solankur, Radhanagari, Kolhapur-416212, India
https://orcid.org/0000-0002-8628-5734
Gurunath Chougale
Department of Chemistry, Shri Yashwantrao Patil Science College, Solankur, Radhanagari, Kolhapur-416212, India
https://orcid.org/0009-0003-9572-1002

Corresponding Author(s) : Nilesh Junghare

nilesh19899@gmail.com

Asian Journal of Chemistry, Vol. 35 No. 11 (2023): Vol 35 Issue 11, 2023

Abstract

An efficient, feasible, transition metal catalyst-free and environmental friendly approach for the synthesis of dithiocarbamate in an ethanol-water solvent combination at room temperature has been established. Alkyl/aryl halide, carbon disulfide and secondary amine were condensed in one pot to produce a range of dithiocarbamate derivatives. Based on the results, the yields were higher when aliphatic amine reacted with benzyl halides as compared to alkyl halides. This method has the advantage of using no hazardous solvents. Other benefits of this method include producing compounds with a good yield by a catalyst-free reaction employing a simple, affordable and useful method. When tested against specific pathogens, selected dithiocarbamate derivatives showed strong antibacterial activity but weak antifungal activity.

Keywords

Green Synthesis Dithiocarbamate Ethanol-water medium Biological activity Catalyst-free synthesis
Junghare, N., Kadam, P., Chavan, J., Patil, M., & Chougale, G. (2023). A Highly Efficient, Catalyst-Free Synthesis of S-Alkyl/aryl Dithiocarbamate Derivatives under Green Conditions and Evaluation of their Biological Activity. Asian Journal of Chemistry, 35(11), 2703–2707. https://doi.org/10.14233/ajchem.2023.28324
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References
  1. T. Erdmenger, C. Guerrero-Sanchez, J. Vitz, R. Hoogenboom and U.S. Schubert, Chem. Soc. Rev., 39, 3317 (2010); https://doi.org/10.1039/b909964f
  2. A. Shaabani, R. Ghadari, A. Sarvary and A.H. Rezayan, J. Org. Chem., 74, 4372 (2009); https://doi.org/10.1021/jo9005427
  3. J. Zhu, Eur. J. Org. Chem., 1133 (2003); https://doi.org/10.1002/ejoc.200390167
  4. A. Chanda and V.V. Fokin, Chem. Rev., 109, 725 (2009); https://doi.org/10.1021/cr800448q
  5. W.N. Kun, S. Mlowe, L.D. Nyamen, P.T. Ndifon, M.A. Malik, O.Q. Munro and N. Revaprasadu, Chem. Eur. J., 22, 13127 (2016); https://doi.org/10.1002/chem.201602106
  6. M.N. Alam, S.K. Mandal and S.C. Debnath, Rubber Chem. Technol., 85, 120 (2012); https://doi.org/10.5254/1.3672434
  7. G. Hogarth, Mini-Rev. Med. Chem., 12, 1202 (2012); https://doi.org/10.2174/138955712802762095
  8. U. Boas, H. Gertz, J.B. Christensen and P.M.H. Heegaard, Tetrahedron Lett., 45, 269 (2004); https://doi.org/10.1016/j.tetlet.2003.10.182
  9. R. Wilhelm and A. Blanrue, Synthesis, 583 (2009); https://doi.org/10.1055/s-0028-1083317
  10. P. Morf, F. Raimondi, H.-G. Nothofer, B. Schnyder, A. Yasuda, J.M. Wessels and T.A. Jung, Langmuir, 22, 658 (2006); https://doi.org/10.1021/la052952u
  11. M. D’hooghe and N. De Kimpe, Tetrahedron, 62, 513 (2006); https://doi.org/10.1016/j.tet.2005.09.028
  12. C. Rafin, E. Veignie, M. Sancholle, D. Postel, C. Len, P. Villa and G. Ronco, J. Agric. Food Chem., 48, 5283 (2000); https://doi.org/10.1021/jf0003698
  13. L. Ronconi, C. Marzano, P. Zanello, M. Corsini, G. Miolo, C. Macca, A. Trevisan and D. Fregona, J. Med. Chem., 49, 1648 (2006); https://doi.org/10.1021/jm0509288
  14. G. Brahemi, F.R. Kona, A. Fiasella, D. Buac, J. Soukupová, A. Brancale, A.M. Burger and A.D. Westwell, J. Med. Chem., 53, 2757 (2010); https://doi.org/10.1021/jm901757t
  15. S.-L. Cao, Y. Han, C.-Z. Yuan, Y. Wang, Z.-K. Xiahou, J. Liao, R.-T. Gao, B.-B. Mao, B.-L. Zhao, Z.-F. Li and X. Xu, Eur. J. Med. Chem., 64, 401 (2013); https://doi.org/10.1016/j.ejmech.2013.04.017
  16. N. Lal, S. Jangir, V. Bala, D. Mandalapu, A. Sarswat, L. Kumar, A. Jain, L. Kumar, B. Kushwaha, A.K. Pandey, S. Krishna, T. Rawat, P.K. Shukla, J.P. Maikhuri, M.I. Siddiqi, G. Gupta and V.L. Sharma, Eur. J. Med. Chem., 115, 275 (2016); https://doi.org/10.1016/j.ejmech.2016.03.012
  17. F. Carta, M. Aggarwal, A. Maresca, A. Scozzafava, R. McKenna, E. Masini and C.T. Supuran, J. Med. Chem., 55, 1721 (2012); https://doi.org/10.1021/jm300031j
  18. G. Turan-Zitouni, A. Özdemir and K. Güven, Arch. Pharm., 338, 96 (2005); https://doi.org/10.1002/ardp.200400935
  19. C.I. Yeo, E.R.T. Tiekink and J. Chew, Inorganics, 9, 48 (2021); https://doi.org/10.3390/inorganics9060048
  20. B. Guo, Z. Ge, T. Cheng and R. Li, Synth. Commun., 31, 3021 (2001); https://doi.org/10.1081/SCC-100105674
  21. S. Levent, U.A. Çevik, B.N. Saglik, Y. Özkay, Ö.D. Can, Ü.D. Özkay and Ü. Uçucu, Phosphorus Sulfur Silicon Relat. Elem., 192, 469 (2017); https://doi.org/10.1080/10426507.2016.1259228
  22. C. Bolzati, M. Cavazza-Ceccato, S. Agostini, F. Refosco, Y. Yamamichi, S. Tokunaga, D. Carta, N. Salvarese, D. Bernardini and G. Bandoli, Bioconjug. Chem., 21, 928 (2010); https://doi.org/10.1021/bc900493e
  23. H. Sudhamani, S.K. Thaslim Basha, S.M.C. Reddy, B. Sreedhar, S. Adam and C. Naga Raju, Res. Chem. Intermed., 42, 7471 (2016); https://doi.org/10.1007/s11164-016-2547-2
  24. A. Asadipour, Z. Shams, K. Eskandari, M.-H. Moshafi, E. Faghih-Mirzaei and Y. Pourshojaei, Res. Chem. Intermed., 44, 1295 (2018); https://doi.org/10.1007/s11164-017-3167-1
  25. K. Biswas, S. Ghosh, P. Ghosh and B. Basu, J. Sulfur Chem., 37, 361 (2016); https://doi.org/10.1080/17415993.2016.1166225
  26. D. Chaturvedi and S. Ray, Tetrahedron Lett., 47, 1307 (2006); https://doi.org/10.1016/j.tetlet.2005.12.079
  27. S. Ahammed, A. Saha and B.C. Ranu, RSC Adv., 2, 6329 (2012); https://doi.org/10.1039/c2ra20856c
  28. S. Ma, J. Liu and X. Xie, Synthesis, 1569 (2012); https://doi.org/10.1055/s-0031-1290811
  29. Q. Sha and Y.-Y. Wei, Org. Biomol. Chem., 11, 5615 (2013); https://doi.org/10.1039/c3ob40745d
  30. N.A. Isley, S. Dobarco and B.H. Lipshutz, Green Chem., 16, 1480 (2014); https://doi.org/10.1039/c3gc42188k
  31. K. Eskandari, B. Karami and S. Khodabakhshi, J. Chem. Res., 38, 600 (2014); https://doi.org/10.3184/174751914X14114871789226
  32. J.H. Clark, Nat. Chem., 1, 12 (2009); https://doi.org/10.1038/nchem.146
  33. A.Z. Halimehjani, F. Ebrahimi, N. Azizi and M.R. Saidi, J. Heterocycl. Chem., 46, 347 (2009); https://doi.org/10.1002/jhet.75
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