Synthesis of [1,3] dithiine derivatives using glycerol:potassium carbonate as green, deep eutectic solvent and evaluation of antibacterial activity against against common bacterial strains between aquatic and human

Document Type : Original Article

Authors

Department of Chemistry, Kerman Branch, Islamic Azad University, Kerman, Iran

Abstract

Introducing new and green methods and finding environmentally friendly solvents in the synthesis of organic compounds is very important. In this study, the synthesis of [1,3] dithiine derivatives using the glycerol: potassium carbonate as deep eutectic solvent was investigated, in addition, the antibacterial effects of the synthesized compounds against two bacterial strains named Edwardsiella tarda and Lactococcus garvieae according to the CLSI standard using microdilution broth base on inhibition zone diameter (IZD), minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) were tested. The results showed that glycerol: potassium carbonate could be used as a green solvent in the synthesis of [1,3] dithiine derivatives and the results of antibacterial activities against study also showed that these compounds, especially f5, were capable of inhibiting Edwardsiella tarda and Lactococcus garvieae at concentrations of 64 and 8 μg / ml, respectively. In addition, it was demonstrated that there was a clear relationship between the structure of the derivatives and the antibacterial activity, with the highest effect being on the chlorine-containing compounds, followed by chlorine, bromine, and nitrogen.

Keywords


[1] M. Nikpassand, l. Z. Fekri, J. Of Applied Chemistry, 51 (1398) 325, in Persian.
[2] S. Behrouz, J. Of Applied Chemistry, 50 (1398) 125, in Persian.
[3] A. Kamel, M. Saleh, Studies in Natural Products Chemistry, 23 (2000) 455.
[4] E. Block, S. Ahmad, M. K. Jain, R. W. Crecely, R. Apitz-Castro, M. R. Cruz, Journal of the American Chemical Society, 106 (1984) 8295.
[5] R. Apitz-Castro, S. Cabrera, M. R. Cruz, H. Ledezma, M.  K. Jain, Thrombosis Research, 32 (1983) 155.
[6] J. K DeMartino, I. Hwang, S. Connelly, I. A. Wilson, D. L. Boger, Journal of Medicinal Chemistry, 51 (2008) 5441.
[7] M. Yamashita, T. Tahara, S. Hayakawa, H. Matsumoto, S. I. Wada, K. Tomioka, A. Iida, Bioorganic & Medicinal Chemistry, 26 (2018) 1920.
[8] K. Chaiseeda, W. Chavasiri, Phosphorus, Sulfur, Silicon and the Related Elements, 19 (2017) 1034.
[9] H. R. Shaterian, H. R. Ahmadian , M. Ghashang, R. Doostmohammadi, H. Yarahmadi, Phosphorus, Sulfur, and Silicon and the Related Elements, 135 (2008) 1099.
[10] H. Mehrabi, Z. Esfandiarpour, T. Davodian, Journal of Sulfur Chemistry, 39 (2018) 164.
[11] P. Xu, G. W. Zheng, M. H. Zong, N. Li, W. Y. Lou, Bioresour. Bioprocess, 4 (2007) 1.
[12] H. Beyzaei, M. K. Deljoo, R. Aryan, B. Ghasemi, M. M. Zahedi, M. Moghaddam‑Manesh, Chemistry Central Journal, 12 (2018) 114.
[13] R. Aryan, H. Beyzaei, M. Nojavan, M. Rezaei, Res Chem Intermed, 43 (2017) 4713.
[14] R. Aryan, H. Beyzaei, M.Nojavan, F. Pirani, H. S. Delarami, M. Sanchooli, Molecular Diversity, 23 (2018) 93.
[15] H. Beyzaei, Z. Motraghi, R. Aryan, M. M. Zahedi, A. Samzadeh-Kermani, Acta Chim. Slov, 64 (2017) 911.
[16] M. D. Daroonkala, H. Kiyani, J. Of Applied Chemistry, 52 (1398) 307, in Persian.
[17] M. Abaszadeh, A. Asadipour, J. Of Applied Chemistry, 47 (1397) 285, in Persian.
[18] L. Santos, F. Ramos, Trends Food Sci. Tech, 52 (2016) 16.
[19] W. H. Ewing, A. C. McWhorter, M. R. Escobar, A. H. Lubin, International Journal of Systematic and Evolutionary Microbiology, 15 (1965) 33.
[20] M. Shahrani, M. Raissy, E. Tajbakhsh, Biological Journal of Microorganism, 11 (2014) 71, in Persian.
 [21] C. Y. Wang, H. S. Shie, S. C. Chen, J. P. Huang, I. C. Hsieh, M. S. Wen, International Journal of Clinical Practice, 61 (2007) 68.
[22] K. Rantsiou, R. Urso, L. Iacumin, C. Cantoni, P. Cattaneo, Applied Environmental Microbiology, 71 (2005) 1977.
[23] C. Ravelo, B. Magarinos, S. LopezRomalde, A. E. Toranzo, J. L. Romalde, Journal of Clinical Microbiology, 41 (2003) 751.
[24] M. G. Carvalho, M. C. Vianni, J. A. Elliot, M. Reeves, R. R. Facklam, Advances in Experimental Medicine and Biology, 418 (1997) 401.
[25] L. A. Deveriese, J. Hommez, H. Laevens, P. B. Adme, F. Haesebrouck, Veterinary Microbiology, 70 (1999) 87.
[26] M. Moghaddam-manesh, S. Hosseinzadegan, H. Beyzaei, The Journal of Urmia University of Medical Sciences, 30 (2019) 163, in Persian.
[27] H. Beyzaei, B. Ghasemi, M. R. Moghadam Manesh, yafte, 18 (2016) 68, in Persian.
[28] J. Naser, F. Mjalli, B. Jibril, S. Al-Hatmi, Z. Gano, International Journal of Chemical Engineering and Applications, 4 (2013) 114.
[29] M. Moghaddam-manesh, D. Ghazanfari, E. Sheikhhosseini, M. Akhgar, ChemistrySelect, 4 (2019) 9247.