Copyright (c) 2021 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Eco-Friendly Novel Synthesis, Characterization of 2,3-Disubstituted 4-Thiazolidinone Derivatives and their Antimicrobial Evaluations
Corresponding Author(s) : Parmesh Kumar Dwivedi
Asian Journal of Chemistry,
Vol. 33 No. 11 (2021): Vol 33 Issue 11, 2021
Abstract
A total of nine derivatives of 4-thiazolidinone were synthesized involving the reaction of benzene-1,2-diamine with 4-aminobenzoic acid followed by reaction with substituted benzaldehyde to get the Schiff bases. These synthesized Schiff bases were further reacted with thioglycolic acid to get the desired thiazolidinones (29-37). In addition to conventional synthesis, the microwave irradiation method has also been employedfor the synthesis of these compounds which provides not only pollution free and eco-friendly environment but also excellent yields. The results showed that 2-substituted thiazolidinone derivatives exhibit good antibacterial activity. It was also recorded that the compounds containing -Cl, -NO2 group with thiazolidinone nucleus are more active than other compounds of the synthesized series.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- Z. Golkar, O. Bagasra and D.G. Pace, J. Infect. Dev. Countr., 8, 129 (2014); https://doi.org/10.3855/jidc.3573
- I.M. Gould and A.M. Bal, Virulence, 4, 185 (2013); https://doi.org/10.4161/viru.22507
- B. Spellberg and D.N. Gilbert, Clin. Infect. Dis., 59(suppl 2), S71 (2014); https://doi.org/10.1093/cid/ciu392
- V.K. Viswanathan, Gut Microbes, 5, 3 (2014); https://doi.org/10.4161/gmic.28027
- C.A. Michael, D. Dominey-Howes and M. Labbate, Front. Public Health, 2, 145 (2014); https://doi.org/10.3389/fpubh.2014.00145
- D. Havrylyuk, B. Zimenkovsky, O. Vasylenko, A. Gzella and R. Lesyk, J. Med. Chem., 55, 8630 (2012); https://doi.org/10.1021/jm300789g
- R. Lesyk and B. Zimenkovsky, Curr. Org. Chem., 8, 1547 (2004); https://doi.org/10.2174/1385272043369773
- M.L. Barreca, A. Chimirri, L. De Luca, A.M. Monforte, P. Monforte, A. Rao, M. Zappala, J. Balzarini, E. De Clercq, C. Pannecouque and M. Witvrouw, Bioorg. Med. Chem. Lett., 11, 1793 (2001); https://doi.org/10.1016/S0960-894X(01)00304-3
- R.K. Rawal, Y.S. Prabhakar, S.B. Katti and E. De Clercq, Bioorg. Med. Chem., 13, 6771 (2005); https://doi.org/10.1016/j.bmc.2005.07.063
- R.K. Rawal, R. Tripathi, S.B. Katti, C. Pannecouque and E. De Clercq, Bioorg. Med. Chem., 15, 1725 (2007); https://doi.org/10.1016/j.bmc.2006.12.003
- J. Balzarini, B. Orzeszko-Krzesiñska, J.K. Maurin and A. Orzeszko, Eur. J. Med. Chem., 44, 303 (2009); https://doi.org/10.1016/j.ejmech.2008.02.039
- P. Vicini, A. Geronikaki, K. Anastasia, M. Incerti and F. Zani, Bioorg. Med. Chem., 14, 3859 (2006); https://doi.org/10.1016/j.bmc.2006.01.043
- S. Bondock, W. Khalifa and A.A. Fadda, Eur. J. Med. Chem., 42, 948 (2007); https://doi.org/10.1016/j.ejmech.2006.12.025
- C.J. Andres, J.J. Bronson, S.V. D’Andrea, M.S. Deshpande, P.J. Falk, K.A. Grant-Young, W.E. Harte, H.-T. Ho, P.F. Misco, J.G. Robertson, D. Stock, Y. Sun and A.W. Walsh, Bioorg. Med. Chem. Lett., 10, 715 (2000); https://doi.org/10.1016/S0960-894X(00)00073-1
- A. Saeed, N. Abbas and U. Flörke, J. Braz. Chem. Soc., 18, 559 (2007); https://doi.org/10.1590/S0103-50532007000300010
- A. Dandia, R. Singh, S. Khaturia, C. Mérienne, G. Morgant and A. Loupy, Bioorg. Med. Chem., 14, 2409 (2006); https://doi.org/10.1016/j.bmc.2005.11.025
- F.L. Gouveia, R.M.B. de Oliveira, T.B. de Oliveira, I.M. da Silva, S.C. do Nascimento, K.X.F.R. de Sena and J.F.C. de Albuquerque, Eur. J. Med. Chem., 44, 2038 (2009); https://doi.org/10.1016/j.ejmech.2008.10.006
- H. Altintas, O. Ates, S. Birteksöz, G. Ötük, M. Uzun and D. Satana, Turk. J. Chem., 29, 425 (2005).
- K.G. Desai, J.P. Raval and K.R. Desai, J. Iran. Chem. Soc., 3, 233 (2006); https://doi.org/10.1007/BF03247213
- P.R. Kumar, M.S. Yadav, M.M. Kumar and T.S. Rao, E-J. Chem., 3, 44 (2006); https://doi.org/10.1155/2006/513489
- M.S.A. El-Gaby, G.A.M. El-Hag Ali, A.A. El-Maghraby, M.T. Abd El-Rahman and M.H.M. Helal, Eur. J. Med. Chem., 44, 4148 (2009); https://doi.org/10.1016/j.ejmech.2009.05.005
- M.G. Vigorita, R. Ottanà, F. Monforte, R. Maccari, M.T. Monforte, A. Trovato, M.F. Taviano, N. Miceli, G. De Luca, S. Alcaro and F. Ortuso, Bioorg. Med. Chem., 11, 999 (2003); https://doi.org/10.1016/S0968-0896(02)00518-7
- A. Kumar, C.S. Rajput and S.K. Bhati, Bioorg. Med. Chem., 15, 3089 (2007); https://doi.org/10.1016/j.bmc.2007.01.042
- S.K. Bhati and A. Kumar, Eur. J. Med. Chem., 43, 2323 (2008); https://doi.org/10.1016/j.ejmech.2007.10.012
- J.R. Jackson, D.R. Patrick, M.M. Dar and P.S. Huang, Nat. Rev. Cancer, 7, 107 (2007); https://doi.org/10.1038/nrc2049
- N. Jiang, X. Wang, Y. Yang and W. Dai, Mini Rev. Med. Chem., 6, 885 (2006); https://doi.org/10.2174/138955706777934955
- S.M. Fitzgerald, B.K. Kemp-Harper, H.C. Parkington, G.A. Head and R.G. Evans, Am. J. Physiol. Regul. Integr. Comp. Physiol., 293, R707 (2007); https://doi.org/10.1152/ajpregu.00807.2006
- V. Calderone, S. Rapposelli, A. Martelli, M. Digiacomo, L. Testai, S. Torri, P. Marchetti, M.C. Breschi and A. Balsamo, Bioorg. Med. Chem., 17, 5426 (2009); https://doi.org/10.1016/j.bmc.2009.06.049
- J. Pepin, C. Guern, L. Ethier, F. Milord, B. Mpia and D. Mansinsa, Lancet, 333, 1246 (1989); https://doi.org/10.1016/S0140-6736(89)92340-4
- T.K. Smith, B.L. Young, H. Denton, D.L. Hughes and G.K. Wagner, Bioorg. Med. Chem. Lett., 19, 1749 (2009); https://doi.org/10.1016/j.bmcl.2009.01.083
- B.A. Bhat, S. Ponnala, D.P. Sahu, P. Tiwari, B.K. Tripathi and A.K. Srivastava, Bioorg. Med. Chem., 12, 5857 (2004); https://doi.org/10.1016/j.bmc.2004.08.031
- P. Alexiou, K. Pegklidou, M. Chatzopoulou, I. Nicolaou and V.J. Demopoulos, Curr. Med. Chem., 16, 734 (2009); https://doi.org/10.2174/092986709787458362
- N.K. Jacob and G.N. Kutty, Indian Drugs, 41, 76 (2004).
- G.K. Nampurath, S.P. Mathew, V. Khanna, R.T. Zachariah, S. Kanji and M.R. Chamallamudi, Chem. Biol. Interact., 171, 363 (2008); https://doi.org/10.1016/j.cbi.2007.10.006
- S.S. Mansoor, K. Aswin, K. Logaiya and S.P.N. Sudhan, J. Saudi Chem. Soc., 19, 379 (2015); https://doi.org/10.1016/j.jscs.2012.04.008
- X. Zhang, Z. Wang, K. Xu, Y. Feng, W. Zhao, X. Xu, Y. Yan and W. Yi, Green Chem., 18, 2313 (2016); https://doi.org/10.1039/C5GC02747K
- J. Jacob, Int. J. Chem., 4, 29 (2012); https://doi.org/10.5539/ijc.v4n6p29
- M. Charde, A. Shukla, V. Bukhariya, J. Mehta and R. Chakole, Int. J. Phytopharm., 2, 39 (2012).
- S. Ravichandran and E. Karthikeyan, Int. J. ChemTech Res., 3, 466 (2011).
- U. Kalidhar and A. Kaur, Res. J. Pharm. Biol. Chem. Sci., 2, 1116 (2011).
- B.N.B. Vaidehi and K.G. Deepika, Int. J. Pharma Bio Sci., 3, 26 (2012).
- S. Demirayak, I. Kayagil and L. Yurttas, Eur. J. Med. Chem., 46, 411 (2011); https://doi.org/10.1016/j.ejmech.2010.11.007
References
Z. Golkar, O. Bagasra and D.G. Pace, J. Infect. Dev. Countr., 8, 129 (2014); https://doi.org/10.3855/jidc.3573
I.M. Gould and A.M. Bal, Virulence, 4, 185 (2013); https://doi.org/10.4161/viru.22507
B. Spellberg and D.N. Gilbert, Clin. Infect. Dis., 59(suppl 2), S71 (2014); https://doi.org/10.1093/cid/ciu392
V.K. Viswanathan, Gut Microbes, 5, 3 (2014); https://doi.org/10.4161/gmic.28027
C.A. Michael, D. Dominey-Howes and M. Labbate, Front. Public Health, 2, 145 (2014); https://doi.org/10.3389/fpubh.2014.00145
D. Havrylyuk, B. Zimenkovsky, O. Vasylenko, A. Gzella and R. Lesyk, J. Med. Chem., 55, 8630 (2012); https://doi.org/10.1021/jm300789g
R. Lesyk and B. Zimenkovsky, Curr. Org. Chem., 8, 1547 (2004); https://doi.org/10.2174/1385272043369773
M.L. Barreca, A. Chimirri, L. De Luca, A.M. Monforte, P. Monforte, A. Rao, M. Zappala, J. Balzarini, E. De Clercq, C. Pannecouque and M. Witvrouw, Bioorg. Med. Chem. Lett., 11, 1793 (2001); https://doi.org/10.1016/S0960-894X(01)00304-3
R.K. Rawal, Y.S. Prabhakar, S.B. Katti and E. De Clercq, Bioorg. Med. Chem., 13, 6771 (2005); https://doi.org/10.1016/j.bmc.2005.07.063
R.K. Rawal, R. Tripathi, S.B. Katti, C. Pannecouque and E. De Clercq, Bioorg. Med. Chem., 15, 1725 (2007); https://doi.org/10.1016/j.bmc.2006.12.003
J. Balzarini, B. Orzeszko-Krzesiñska, J.K. Maurin and A. Orzeszko, Eur. J. Med. Chem., 44, 303 (2009); https://doi.org/10.1016/j.ejmech.2008.02.039
P. Vicini, A. Geronikaki, K. Anastasia, M. Incerti and F. Zani, Bioorg. Med. Chem., 14, 3859 (2006); https://doi.org/10.1016/j.bmc.2006.01.043
S. Bondock, W. Khalifa and A.A. Fadda, Eur. J. Med. Chem., 42, 948 (2007); https://doi.org/10.1016/j.ejmech.2006.12.025
C.J. Andres, J.J. Bronson, S.V. D’Andrea, M.S. Deshpande, P.J. Falk, K.A. Grant-Young, W.E. Harte, H.-T. Ho, P.F. Misco, J.G. Robertson, D. Stock, Y. Sun and A.W. Walsh, Bioorg. Med. Chem. Lett., 10, 715 (2000); https://doi.org/10.1016/S0960-894X(00)00073-1
A. Saeed, N. Abbas and U. Flörke, J. Braz. Chem. Soc., 18, 559 (2007); https://doi.org/10.1590/S0103-50532007000300010
A. Dandia, R. Singh, S. Khaturia, C. Mérienne, G. Morgant and A. Loupy, Bioorg. Med. Chem., 14, 2409 (2006); https://doi.org/10.1016/j.bmc.2005.11.025
F.L. Gouveia, R.M.B. de Oliveira, T.B. de Oliveira, I.M. da Silva, S.C. do Nascimento, K.X.F.R. de Sena and J.F.C. de Albuquerque, Eur. J. Med. Chem., 44, 2038 (2009); https://doi.org/10.1016/j.ejmech.2008.10.006
H. Altintas, O. Ates, S. Birteksöz, G. Ötük, M. Uzun and D. Satana, Turk. J. Chem., 29, 425 (2005).
K.G. Desai, J.P. Raval and K.R. Desai, J. Iran. Chem. Soc., 3, 233 (2006); https://doi.org/10.1007/BF03247213
P.R. Kumar, M.S. Yadav, M.M. Kumar and T.S. Rao, E-J. Chem., 3, 44 (2006); https://doi.org/10.1155/2006/513489
M.S.A. El-Gaby, G.A.M. El-Hag Ali, A.A. El-Maghraby, M.T. Abd El-Rahman and M.H.M. Helal, Eur. J. Med. Chem., 44, 4148 (2009); https://doi.org/10.1016/j.ejmech.2009.05.005
M.G. Vigorita, R. Ottanà, F. Monforte, R. Maccari, M.T. Monforte, A. Trovato, M.F. Taviano, N. Miceli, G. De Luca, S. Alcaro and F. Ortuso, Bioorg. Med. Chem., 11, 999 (2003); https://doi.org/10.1016/S0968-0896(02)00518-7
A. Kumar, C.S. Rajput and S.K. Bhati, Bioorg. Med. Chem., 15, 3089 (2007); https://doi.org/10.1016/j.bmc.2007.01.042
S.K. Bhati and A. Kumar, Eur. J. Med. Chem., 43, 2323 (2008); https://doi.org/10.1016/j.ejmech.2007.10.012
J.R. Jackson, D.R. Patrick, M.M. Dar and P.S. Huang, Nat. Rev. Cancer, 7, 107 (2007); https://doi.org/10.1038/nrc2049
N. Jiang, X. Wang, Y. Yang and W. Dai, Mini Rev. Med. Chem., 6, 885 (2006); https://doi.org/10.2174/138955706777934955
S.M. Fitzgerald, B.K. Kemp-Harper, H.C. Parkington, G.A. Head and R.G. Evans, Am. J. Physiol. Regul. Integr. Comp. Physiol., 293, R707 (2007); https://doi.org/10.1152/ajpregu.00807.2006
V. Calderone, S. Rapposelli, A. Martelli, M. Digiacomo, L. Testai, S. Torri, P. Marchetti, M.C. Breschi and A. Balsamo, Bioorg. Med. Chem., 17, 5426 (2009); https://doi.org/10.1016/j.bmc.2009.06.049
J. Pepin, C. Guern, L. Ethier, F. Milord, B. Mpia and D. Mansinsa, Lancet, 333, 1246 (1989); https://doi.org/10.1016/S0140-6736(89)92340-4
T.K. Smith, B.L. Young, H. Denton, D.L. Hughes and G.K. Wagner, Bioorg. Med. Chem. Lett., 19, 1749 (2009); https://doi.org/10.1016/j.bmcl.2009.01.083
B.A. Bhat, S. Ponnala, D.P. Sahu, P. Tiwari, B.K. Tripathi and A.K. Srivastava, Bioorg. Med. Chem., 12, 5857 (2004); https://doi.org/10.1016/j.bmc.2004.08.031
P. Alexiou, K. Pegklidou, M. Chatzopoulou, I. Nicolaou and V.J. Demopoulos, Curr. Med. Chem., 16, 734 (2009); https://doi.org/10.2174/092986709787458362
N.K. Jacob and G.N. Kutty, Indian Drugs, 41, 76 (2004).
G.K. Nampurath, S.P. Mathew, V. Khanna, R.T. Zachariah, S. Kanji and M.R. Chamallamudi, Chem. Biol. Interact., 171, 363 (2008); https://doi.org/10.1016/j.cbi.2007.10.006
S.S. Mansoor, K. Aswin, K. Logaiya and S.P.N. Sudhan, J. Saudi Chem. Soc., 19, 379 (2015); https://doi.org/10.1016/j.jscs.2012.04.008
X. Zhang, Z. Wang, K. Xu, Y. Feng, W. Zhao, X. Xu, Y. Yan and W. Yi, Green Chem., 18, 2313 (2016); https://doi.org/10.1039/C5GC02747K
J. Jacob, Int. J. Chem., 4, 29 (2012); https://doi.org/10.5539/ijc.v4n6p29
M. Charde, A. Shukla, V. Bukhariya, J. Mehta and R. Chakole, Int. J. Phytopharm., 2, 39 (2012).
S. Ravichandran and E. Karthikeyan, Int. J. ChemTech Res., 3, 466 (2011).
U. Kalidhar and A. Kaur, Res. J. Pharm. Biol. Chem. Sci., 2, 1116 (2011).
B.N.B. Vaidehi and K.G. Deepika, Int. J. Pharma Bio Sci., 3, 26 (2012).
S. Demirayak, I. Kayagil and L. Yurttas, Eur. J. Med. Chem., 46, 411 (2011); https://doi.org/10.1016/j.ejmech.2010.11.007