Main Article Content
Abstract
In this paper, thiosemicarbazone derivatives have been prepared from substituted aromatic aldehyde and thiosemicarbazide in presence of sodium chloride. This method is an efficient, mild, inexpensive, non-toxic and environment benign catalyst. This protocol includes the reaction followed by using sodium chloride to accelerate the reaction in aqueous ethanol. The structure of synthesized compounds were determined by IR, 1H NMR, 13C NMR and mass spectroscopies as well as the compounds were also screened for antibacterial and antifungal activity against certain Gram-negative and Gram-positive bacteria and fungal pathogens.
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References
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- J.B. Gujar, M.A. Chaudhari, D.S. Kawade and M.S. Shingare, Sodium Chloride: A Proficient Additive for the Synthesis of Pyridine Derivatives in Aqueous Medium, Tetrahedron Lett., 55, 6939 (2014); https://doi.org/10.1016/j.tetlet.2014.10.125.
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- N. Parul, N. Subhangkar and A. Mahato, Antimicrobial Activity of Different Thiosemicarbazone Compounds Against Microbial Pathogens, Int. Res. J. Pharm., 3, 350 (2012).
- G. Pelosi, Thiosemicarbazone Metal Complexes: From Structure to Activity, Open Crystallogr. J., 3, 16 (2010); https://doi.org/10.2174/1874846501003010016.
- A.K. Kaplancikli, M.D. Altintop, B. Sever, Z. Canturk and A. Ozdemir, Synthesis and in vitro Evaluation of New Thiosemicarbazone Derivatives as Potential Antimicrobial Agents, J. Chem., 2016, Article ID 1692540 (2016); https://doi.org/10.1155/2016/1692540.
- M. Kalhor, M. Shabani, I. Nikokar and S.R. Banisaeed, Synthesis, Characterization and Antibacterial Activity of Some Novel Thiosemi-carbazides, 1,2,4-Triazol-3-thiols and their S-Substituted Derivatives, Iran. J. Pharm. Res., 14, 67 (2015).
- M.A. Souza, S. Johann, L.A.R. dos Santos Lima, F.F. Campos, I.C. Mendes, H. Beraldo, E.M. de Souza-Fagundes, P.S. Cisalpino, C.A. Rosa, T.M. de Almeida Alves, N.P. de Sá and C.L. Zani, The Antimicrobial Activity of Lapachol and Its Thiosemicarbazone and Semicarbazone Derivatives, Mem. Inst. Oswaldo Cruz. Rio de Janeiro, 108, 342 (2013); https://doi.org/10.1590/S0074-02762013000300013.
- H.M. Zakir, M. Jesmin and S.M.M. Ali, Antibacterial Activities of Benzoin Thiosemicarbazone and Its Complexes with Co(II) and Ni(II), Asian J. Med. Pharm., 6, 32 (2016).
- R.J. Nevagi and A.S. Dhake, Antibacterial Activity of Thiosemicarbazide Derivatives, Der Pharm. Chem., 5, 45 (2013).
- M. Pitucha, M. Wos, M. Miazga-Karska, K. Klimek, B. Miroslaw, A. Pachuta-Stec, A. Gladysz and G. Ginalska, Synthesis, Antibacterial and Antiproliferative Potential of Some New 1-pyridinecarbonyl-4-substi-tuted Thiosemicarbazide Derivatives, Med. Chem. Res., 25, 1666 (2016); https://doi.org/10.1007/s00044-016-1599-6.
- R.K. Agarwal, L. Singh and D.K. Sharma, Synthesis, Spectral and Biological Properties of Copper(II) Complexes of Thiosemicarbazones of Schiff Bases Derived from 4-Aminoantipyrine and Aromatic Aldehydes, Bioinorg. Chem. Appl., 2006, Article ID 59509 (2006); https://doi.org/10.1155/BCA/2006/59509.
- E. Pahontu, F. Julea, R. Rosu, V. Purcarea, Y. Chumakov, P. Petrenco and J. Gulea, Antibacterial, Antifungal and in vitro Antileukaemia Activity of Metal Complexes with Thiosemicarbazones, Cell. Mol. Med., 19, 865 (2015); https://doi.org/10.1111/jcmm.12508.
- G. Singh and S. Sharma, Synthesis and Antimicrobial Activity of Thio-semicarbazone Induced Hydrazone of 2-Anilino-3-formylchromone, J. Chem. Pharm. Res., 7, 599 (2015).
- R. Tada, N. Chavda and M. Shah, Synthesis and Characterization of Some New Thiosemicarbazide Derivatives and their Transition Metal Complexes, J. Chem. Pharm. Res., 3, 290 (2011).
- V. Pradhan, M. Farooqui, T.A. Khan, P.A. Khan and J.V. Khan, Anti-microbial Activity of Caesulia axillaris Roxb and Psoralea corylifolia L., World J. Pharm. Res., 6, 352 (2017).
- B. Zine, S. Jadhav and M. Farooqui, Design, Synthesis and Biological Evaluation of Dihydroisoxazole of Indole Derivatives as Anti-microbial Agents, J. Chem. Pharm. Res., 8, 234 (2016).
References
N.A. Mirgane and A.V. Karnik, Aqueous Ethanol: A Suitable Medium for the Diastereoselective Diels-Alder Reaction Mediated by Chiral Bases, Green Chem. Lett. Rev., 4, 269 (2011); https://doi.org/10.1080/17518253.2011.571715.
J.B. Gujar, M.A. Chaudhari, D.S. Kawade and M.S. Shingare, Sodium Chloride: A Proficient Additive for the Synthesis of Pyridine Derivatives in Aqueous Medium, Tetrahedron Lett., 55, 6939 (2014); https://doi.org/10.1016/j.tetlet.2014.10.125.
A. Khandebharad, S. Sards, M. Soni, C. Gill, P. Kulkarni and B. Agrawal, NaCl: A Facile, Environmentally Benign Catalyst for the Synthesis of Pyrazole 4-carbonitrile in Aqueous Media, Curr. Chem. Lett., 7, 57 (2018); https://doi.org/10.5267/j.ccl.2018.3.003.
N. Parul, N. Subhangkar and A. Mahato, Antimicrobial Activity of Different Thiosemicarbazone Compounds Against Microbial Pathogens, Int. Res. J. Pharm., 3, 350 (2012).
G. Pelosi, Thiosemicarbazone Metal Complexes: From Structure to Activity, Open Crystallogr. J., 3, 16 (2010); https://doi.org/10.2174/1874846501003010016.
A.K. Kaplancikli, M.D. Altintop, B. Sever, Z. Canturk and A. Ozdemir, Synthesis and in vitro Evaluation of New Thiosemicarbazone Derivatives as Potential Antimicrobial Agents, J. Chem., 2016, Article ID 1692540 (2016); https://doi.org/10.1155/2016/1692540.
M. Kalhor, M. Shabani, I. Nikokar and S.R. Banisaeed, Synthesis, Characterization and Antibacterial Activity of Some Novel Thiosemi-carbazides, 1,2,4-Triazol-3-thiols and their S-Substituted Derivatives, Iran. J. Pharm. Res., 14, 67 (2015).
M.A. Souza, S. Johann, L.A.R. dos Santos Lima, F.F. Campos, I.C. Mendes, H. Beraldo, E.M. de Souza-Fagundes, P.S. Cisalpino, C.A. Rosa, T.M. de Almeida Alves, N.P. de Sá and C.L. Zani, The Antimicrobial Activity of Lapachol and Its Thiosemicarbazone and Semicarbazone Derivatives, Mem. Inst. Oswaldo Cruz. Rio de Janeiro, 108, 342 (2013); https://doi.org/10.1590/S0074-02762013000300013.
H.M. Zakir, M. Jesmin and S.M.M. Ali, Antibacterial Activities of Benzoin Thiosemicarbazone and Its Complexes with Co(II) and Ni(II), Asian J. Med. Pharm., 6, 32 (2016).
R.J. Nevagi and A.S. Dhake, Antibacterial Activity of Thiosemicarbazide Derivatives, Der Pharm. Chem., 5, 45 (2013).
M. Pitucha, M. Wos, M. Miazga-Karska, K. Klimek, B. Miroslaw, A. Pachuta-Stec, A. Gladysz and G. Ginalska, Synthesis, Antibacterial and Antiproliferative Potential of Some New 1-pyridinecarbonyl-4-substi-tuted Thiosemicarbazide Derivatives, Med. Chem. Res., 25, 1666 (2016); https://doi.org/10.1007/s00044-016-1599-6.
R.K. Agarwal, L. Singh and D.K. Sharma, Synthesis, Spectral and Biological Properties of Copper(II) Complexes of Thiosemicarbazones of Schiff Bases Derived from 4-Aminoantipyrine and Aromatic Aldehydes, Bioinorg. Chem. Appl., 2006, Article ID 59509 (2006); https://doi.org/10.1155/BCA/2006/59509.
E. Pahontu, F. Julea, R. Rosu, V. Purcarea, Y. Chumakov, P. Petrenco and J. Gulea, Antibacterial, Antifungal and in vitro Antileukaemia Activity of Metal Complexes with Thiosemicarbazones, Cell. Mol. Med., 19, 865 (2015); https://doi.org/10.1111/jcmm.12508.
G. Singh and S. Sharma, Synthesis and Antimicrobial Activity of Thio-semicarbazone Induced Hydrazone of 2-Anilino-3-formylchromone, J. Chem. Pharm. Res., 7, 599 (2015).
R. Tada, N. Chavda and M. Shah, Synthesis and Characterization of Some New Thiosemicarbazide Derivatives and their Transition Metal Complexes, J. Chem. Pharm. Res., 3, 290 (2011).
V. Pradhan, M. Farooqui, T.A. Khan, P.A. Khan and J.V. Khan, Anti-microbial Activity of Caesulia axillaris Roxb and Psoralea corylifolia L., World J. Pharm. Res., 6, 352 (2017).
B. Zine, S. Jadhav and M. Farooqui, Design, Synthesis and Biological Evaluation of Dihydroisoxazole of Indole Derivatives as Anti-microbial Agents, J. Chem. Pharm. Res., 8, 234 (2016).