[(C3H7)3N-SO3H]Cl: An Efficient Ionic Liquid Catalyst for the Synthesis of Oxoindolin Hydrazine carbothioamide Derivatives and their Antimicrobial Evaluation

Volume 14, Issue 53, 2025 (January – March)


Research Article
[(C3H7)3N-SO3H]Cl: An Efficient Ionic Liquid Catalyst for the Synthesis of Oxoindolin Hydrazine carbothioamide Derivatives and their Antimicrobial Evaluation
Shivaji Sawant, Pradeep Patil, Govind Salunke, Sandeep Sankpal, Shankar Hangirgekar
Keywords: Anti-microbial activity; Aqueous medium; Ionic liquid; Recyclable catalyst; oxoindolin hydrazine carbothioamide.
DOI:10.37273/chesci.cs205509281


 

Received : 28.09.2024 | Revised : 28.10.2024 | Accepted : 30.10.2024 | Online : 31.01.2025


Full Text – PDF

Abstract
In the present study, we disclose a efficient synthesis of oxoindolin hydrazine carbothioamide derivatives catalyzed by Brønsted acidic [(C3H7)3N-SO3H]Cl ionic liquid. The synthesized BAIL represents an efficient catalyst for the reaction of isatin and thiosemicarbazide for the synthesis of oxoindolin hydrazine carbothioamide by a one-pot synthesis in an aqueous solution at ambient conditions. The significant features of the protocol includes use of green solvent, simple operational and work-up procedures, high yield, shorter reaction times and recyclability of ionic liquid catalyst, etc. Moreover, the synthesized oxoindolin hydrazine carbothioamides were screened for antimicrobial activity against pathogenic bacteria E. coli and S. aureus. The compound, 3j show the most remarkable anti-microbial activity as compared to commercial drugs.


References
[1] L. Zhou, F. Lv, L. Liu, S. Wang, Acc. Chem. Res. 52, 3211 (2019).
[2] D. Lenoir, K. W. Schramm, J. O. Lalah, Sustain. Chem. Pharm. 18, 100313 (2020).
[3] J. Becker, C. Manske, S. Randl, Curr. Opin. Green Sustain. Chem. 33, 100562 (2022).
[4] N. Ullah, M. Tuzen. Green Chem. 25, 1729 (2023).
[5] T. Kitanosono, K. Masuda, P. Xu, S. Kobayashi, Chem. Rev. 118, 679 (2018).
[6] M. A. Alotaibi, M. A. Bakht, A. I. Alharthi, M. H. Geesi, M. B. Alshammari, Y. Riadi, Sustain. Chem. Pharm. 17, 100279 (2020).
[7] H. G. Alvim, J. R. Correa, Assumpção, W. A. da Silva, M. O. Rodrigues, J. L. de Macedo, B. A. Neto, J. Org. Chem. 83, 4044 (2018).
[8] Y. Zhao, B. Han, Z. Liu, Acc. Chem. Res. 54, 3172 (2021).
[9] P. Sarma, A. K. Dutta, R. Borah, Catal. Surv. Asia. 21, 70 (2017).
[10] T. Akiyama, K. Mori, Chem. Rev. Chem. Rev. 115, 9277 (2015).
[11] L. Saini, A. Jain, U. Bhadoriya. Asian J. Pharm. Sci.1, 4423 (2011).
[12] S.S. Karki, A.A. Kulkarni, S. Kumar, Med. Chem. Res. 22, 2014 (2013).
[13] S. Ahn, H. Yeo, E. Jung, Y. Lee, D. Koh, H. Lee, S. Y. Shin, Bioorg. Chem. 148, 107481 (2024).
[14] Y. S. Li, B. Peng, L. Ma, S. L. Cao, L. L. Bai, C. R. Yang, X. Xu, Eur. J. Med. Chem. 127, 137 (2017).
[15] A. Gera, C. Mohan, J. Madan, S. Arora, Curr. Org. Synth. 16, 1055 (2019).
[16] L. L. S. F. R. Dantas, A. G. Fonseca, J. R. Pereira, A. A. Furtado, P. A. T. M. Gomes, M. F. Fernandes-Pedrosa, T. M. A. M. Lemos, Braz. J. Med. Biol. Res. 53, e10204 (2020).
[17] V. F.S. Pape, S. Tóth, A. Füredi, K. Szebényi, A. Lovrics, P. Szabó, G. Szakács, Eur. J. Med. Chem. 117, 335 (2016).
[18] T. A. Fadla, A. A. Radwan, H. A. Abdelaziz, M. Baseeruddin, M. I. Attiaa, A. Kadi, Dig. J. Nanomater. Bios. 7, 327 (2012).
[19] S.Y. Abbas, A.A. Farag, Y. A. Ammar, Monatsh Chem. 144, 1725 (2013).
[20] A. Parlapalli, R. V. Kumar, M. Cidda, S. Manda, J. Chem. Pharm. Res. 12, 979 (2017).
[21] M. A. Baashen, J. Heterocycl. Chem. 56, 1953 (2019).
[22] N. D. Thanh, N. T. K. Giang, T. H. Quyen, D. T. Huong, V. N. Toan, Eur. J. Med. Chem. 123, 532 (2016).
[23] K.N. Aneesrahman, K. Ramaiah, G. Rohini, G.P. Stefy, N.S.P. Bhuvanesh, A. Sreekanth, Inorganica. Chimica. Acta. 492, 131 (2019).
[24] H. Sachdeva, D. Dwivedi, K. Arya, S. Khaturia, R. Saroj, Med. Chem. Res. 22, 4953 (2013).
[25] A. Khazaei, M. A. Zolfigol, A. R. Moosavi-Zare, J. Afsar, A. Zare, V. Khakyzadeh, M. H. Beyzavi, Chinese J. Catal.34, 1936 (2013).
[26] P. Patil, A. Yadav, L. Bavkar, B. N. Nippu, N. D. Satyanarayan, A. Mane, S. Sankpal, J. Mol. Struct.1242, 130672 (2021).
[27] E. S. Armengol, M. Harmanci, F. Laffleur, Microbiol. Res. 252, 126867 (2021).
[28] G. Chavez-Esquivel, H. Cervantes-Cuevas, L. F. Ybieta-Olvera, M. C. Briones, D. Acosta, J. Cabello, Mater. Sci. Eng. C, 123, 111934 (2021).


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