Copyright (c) 2023 K. SUNITHA, SMITHA NAIR, P. PALANISAMY
This work is licensed under a Creative Commons Attribution 4.0 International License.
In vitro Antidiabetic and Anticancer Activity of Some Novel Diazenyl Benzene Sulphonamide Derivatives
Corresponding Author(s) : SMITHA NAIR
Asian Journal of Chemistry,
Vol. 35 No. 10 (2023): Vol 35 Issue 10, 2023
Abstract
A series of novel 2-[(5-phenyl-1,3,4-thiadiazole-2-imino)substituted benzene]diazenyl benzene sulphonamide derivatives (VII)6-10 were
synthesized and FT-IR, 1H NMR, 13C NMR and GC-MS spectral data were used to investigate the structures of the synthesized sulphonamide derivatives. The antioxidant activity of 2-[(5-phenyl-1,3,4-thiadiazole-2-imino)substituted benzene]diazenyl benzene sulphonamide derivatives (VII)6-10 was done using DPPH technique. Compounds (VII)7 and (VII)9 displayed excellent antioxidant activity when compared to standard ascorbic acid. The in vitro antidiabetic activity on α-amylase and α-glucosidase studies indicated compound (VII)7 as promising inhibitor of α-amylase and α-glucosidase. The cytotoxic activity of the synthesized compound (VII)9 was tested against human colon (HCT-116), lung (A549), breast (MCF-7) cancer cell lines and fibroblast (L929) normal mouse lines. The results showed that compound (VII)9 has good cytotoxic activity.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- E. Eroglu, Int. J. Mol. Sci., 9, 181 (2008); https://doi.org/10.3390/ijms9020181
- C.T. Supuran, A. Casini, A. Mastrolorenzo and A. Scozzafava, Mini Rev. Med. Chem., 4, 625 (2004); https://doi.org/10.2174/1389557043403792
- R. Kasimogullari, M. Bülbül, H. Günhan and H. Güleryüz, Bioorg. Med. Chem., 17, 3295 (2009); https://doi.org/10.1016/j.bmc.2009.03.048
- M. Bülbül, R. Kasimogullari and Ö.I. Küfrevioglu, J. Enzyme Inhib. Med. Chem., 23, 895 (2008); https://doi.org/10.1080/14756360701626173
- A. Scozzafava, T. Owa, A. Mastrolorenzo and C.T. Supuran, Curr. Med. Chem., 10, 925 (2003); https://doi.org/10.2174/0929867033457647
- Z.H. Chohan, Mahmood-ul-Hassan, K.M. Khan and C.T. Supuran, J. Enzyme Inhib. Med. Chem., 20, 183 (2005); https://doi.org/10.1080/14756360500043257
- A. Scozzafava, M.D. Banciu, A. Popescu and C.T. Supuran, J. Enzyme Inhib., 15, 443 (2000); https://doi.org/10.3109/14756360009040700
- B.L. Wilkinson, L.F. Bornaghi, T.A. Houston, A. Innocenti, D. Vullo, C.T. Supuran and S.A. Poulsen, Bioorg. Med. Chem. Lett., 17, 987 (2007); https://doi.org/10.1016/j.bmcl.2006.11.046
- A. Alsughayer, A.-Z.A. Elassar, S. Mustafa and F.A. Sagheer, J. Biomater. Nanobiotechnol., 2, 144 (2011); https://doi.org/10.4236/jbnb.2011.22018
- O. Guzel, A. Maresca, A. Scozzafava, A. Salman, A.T. Balaban and C.T. Supuran, J. Med. Chem., 52, 4063 (2009); https://doi.org/10.1021/jm9004016
- A.K. Jain, S. Sharma, A. Vaidya, V. Ravichandran and R.K. Agrawal, Chem. Biol. Drug Des., 81, 557 (2013); https://doi.org/10.1111/cbdd.12125
- T. Manimaran, R.M. Anand and M. Jishala, Int. J. Pharm. Chem. Biol. Sci., 7, 142 (2017).
- P. Li, L. Shi, M. Gao, X. Yang, W. Xue, L. Jin, D. Hu and B. Song, Bioorg. Med. Chem. Lett., 25, 481 (2015); https://doi.org/10.1016/j.bmcl.2014.12.038
- P. Mullick, S.A. Khan, S. Verma and O. Alam, Bull. Korean Chem. Soc., 31, 2345 (2010); https://doi.org/10.5012/bkcs.2010.31.8.2345
- Y. Hu, C.-Y. Li, X.-M. Wang, Y.-H. Yang and H.-L. Zhu, Chem. Rev., 114, 5572 (2014); https://doi.org/10.1021/cr400131u
- W.S. Hamama, H.A. Raoof, H.H. Zoorob and M.E. Ibrahim, Der Pharma Chem., 9, 28 (2017).
- M.A. Gouda and B.H. Hussein, Lett. Drug Des. Discov., 14, 1425 (2017); https://doi.org/10.2174/1570180814666170607144811
- A. Ovung and J. Bhattacharyya, Biophys. Rev., 13, 259 (2021);https://doi.org/10.1007/s12551-021-00795-9
- M. Berredjem, F. Bouchareb, S.-E. Djouad, R. Bouasla, R. Bahadi, R. Redjemia, M. Boussaker and A. Dekir, ChemistrySelect, 8, e202301859 (2023); https://doi.org/10.1002/slct.202301859
- M.S.A. El-Gabya, Y.A. Ammar, M.I.H. El-Qaliei, A.M. Ali, M.F. Hussein and F.A. Faraghally, Egypt. J. Chem., 63, 5289 (2020); https://doi.org/10.21608/EJCHEM.2020.33860.2707
- V. Jatav, P. Mishra, S. Kashaw and J.P. Stables, Eur. J. Med. Chem., 43, 135 (2008); https://doi.org/10.1016/j.ejmech.2007.02.004
- B. Kumaraswamy, K.T. Ranjith, S. Narasimha and R.N. Vasudeva, Int. J. Pharm. Pharm. Sci., 6, 572 (2014).
- K.K. Jithendra, G.S. Krishnamurthy and K. Sunil, Int. J. Pharm. Pharm. Sci., 8, 134 (2016).
- O. Bekircan, B. Kahveci and M. Kucuk, Turk. J. Chem., 30, 29 (2006).
- O. Bekircan and H. Bektas, Molecules, 13, 2126 (2008); https://doi.org/10.3390/molecules13092126
- B. Kahveci, O. Bekircan and S.A. Karaoglu, Indian J. Chem., 44B, 2614 (2005).
- C. Park, J.-S. Lim, Y. Lee, B. Lee, S.-W. Kim, J. Lee and S. Kim, Enzyme Microb. Technol., 40, 1758 (2007); https://doi.org/10.1016/j.enzmictec.2006.12.005
- N. Raman, L. Mitu, A. Sakthivel and M.S.S. Pandi, J. Iran. Chem. Soc., 6, 738 (2009).
- M. Hernandes, S.M. Cavalcanti, D.R. Moreira, W. de Azevedo Junior and A.C. Leite, Curr. Drug Targets, 11, 303 (2010); https://doi.org/10.2174/138945010790711996
- A. Casini, A. Scozzafava and A.C.T. Supuran, Expert Opin. Ther. Pat., 12, 1307 (2002); https://doi.org/10.1517/13543776.12.9.1307
- C.T. Supuran, A. Scozzafava, L. Menabuoni, F. Mincione, F. Briganti and G. Mincione, Eur. J. Pharm. Sci., 8, 317 (1999); https://doi.org/10.1016/S0928-0987(99)00022-6
- M. Remko and C.-W. von der Lieth, Bioorg. Med. Chem., 12, 5395 (2004); https://doi.org/10.1016/j.bmc.2004.07.049
- A.K. Gadad, C.S. Mahajanshetti, S. Nimbalkar and A. Raichurkar, Eur. J. Med. Chem., 35, 853 (2000); https://doi.org/10.1016/S0223-5234(00)00166-5
- G.H. Elgemeie, R.A. Azzam and R.E. Elsayed, Med. Chem. Res., 28, 1099 (2019); https://doi.org/10.1007/s00044-019-02378-6
- B.R. Stranix, J.F. Lavallee, G. Sevigny, J. Yelle, V. Perron, N. LeBerre, D. Herbart and J.J. Wu, Bioorg. Med. Chem. Lett., 16, 3459 (2006); https://doi.org/10.1016/j.bmcl.2006.04.011
- K. Sunitha, S. Nair and P. Palanisamy, Asian J. Chem., 34, 663 (2022); https://doi.org/10.14233/ajchem.2022.23591
- P. Bernfeld, eds: S.P. Colowick and N.O. Kaplan, Amylase, a and b in Methods in Enzymology, Academic Press; New York, NY, USA, pp. 149-158 (1955).
- M.C. Alley, D.A. Scudiero, A. Monks, M.L. Hursey, M.J. Czerwinski, D.L. Fine, B.J. Abbott, J.G. Mayo, R.H Shoemaker and M.R. Boyd, Cancer Res., 48, 589 (1988).
- T. Mosmann, J. Immunol. Methods, 65, 55 (1983); https://doi.org/10.1016/0022-1759(83)90303-4
References
E. Eroglu, Int. J. Mol. Sci., 9, 181 (2008); https://doi.org/10.3390/ijms9020181
C.T. Supuran, A. Casini, A. Mastrolorenzo and A. Scozzafava, Mini Rev. Med. Chem., 4, 625 (2004); https://doi.org/10.2174/1389557043403792
R. Kasimogullari, M. Bülbül, H. Günhan and H. Güleryüz, Bioorg. Med. Chem., 17, 3295 (2009); https://doi.org/10.1016/j.bmc.2009.03.048
M. Bülbül, R. Kasimogullari and Ö.I. Küfrevioglu, J. Enzyme Inhib. Med. Chem., 23, 895 (2008); https://doi.org/10.1080/14756360701626173
A. Scozzafava, T. Owa, A. Mastrolorenzo and C.T. Supuran, Curr. Med. Chem., 10, 925 (2003); https://doi.org/10.2174/0929867033457647
Z.H. Chohan, Mahmood-ul-Hassan, K.M. Khan and C.T. Supuran, J. Enzyme Inhib. Med. Chem., 20, 183 (2005); https://doi.org/10.1080/14756360500043257
A. Scozzafava, M.D. Banciu, A. Popescu and C.T. Supuran, J. Enzyme Inhib., 15, 443 (2000); https://doi.org/10.3109/14756360009040700
B.L. Wilkinson, L.F. Bornaghi, T.A. Houston, A. Innocenti, D. Vullo, C.T. Supuran and S.A. Poulsen, Bioorg. Med. Chem. Lett., 17, 987 (2007); https://doi.org/10.1016/j.bmcl.2006.11.046
A. Alsughayer, A.-Z.A. Elassar, S. Mustafa and F.A. Sagheer, J. Biomater. Nanobiotechnol., 2, 144 (2011); https://doi.org/10.4236/jbnb.2011.22018
O. Guzel, A. Maresca, A. Scozzafava, A. Salman, A.T. Balaban and C.T. Supuran, J. Med. Chem., 52, 4063 (2009); https://doi.org/10.1021/jm9004016
A.K. Jain, S. Sharma, A. Vaidya, V. Ravichandran and R.K. Agrawal, Chem. Biol. Drug Des., 81, 557 (2013); https://doi.org/10.1111/cbdd.12125
T. Manimaran, R.M. Anand and M. Jishala, Int. J. Pharm. Chem. Biol. Sci., 7, 142 (2017).
P. Li, L. Shi, M. Gao, X. Yang, W. Xue, L. Jin, D. Hu and B. Song, Bioorg. Med. Chem. Lett., 25, 481 (2015); https://doi.org/10.1016/j.bmcl.2014.12.038
P. Mullick, S.A. Khan, S. Verma and O. Alam, Bull. Korean Chem. Soc., 31, 2345 (2010); https://doi.org/10.5012/bkcs.2010.31.8.2345
Y. Hu, C.-Y. Li, X.-M. Wang, Y.-H. Yang and H.-L. Zhu, Chem. Rev., 114, 5572 (2014); https://doi.org/10.1021/cr400131u
W.S. Hamama, H.A. Raoof, H.H. Zoorob and M.E. Ibrahim, Der Pharma Chem., 9, 28 (2017).
M.A. Gouda and B.H. Hussein, Lett. Drug Des. Discov., 14, 1425 (2017); https://doi.org/10.2174/1570180814666170607144811
A. Ovung and J. Bhattacharyya, Biophys. Rev., 13, 259 (2021);https://doi.org/10.1007/s12551-021-00795-9
M. Berredjem, F. Bouchareb, S.-E. Djouad, R. Bouasla, R. Bahadi, R. Redjemia, M. Boussaker and A. Dekir, ChemistrySelect, 8, e202301859 (2023); https://doi.org/10.1002/slct.202301859
M.S.A. El-Gabya, Y.A. Ammar, M.I.H. El-Qaliei, A.M. Ali, M.F. Hussein and F.A. Faraghally, Egypt. J. Chem., 63, 5289 (2020); https://doi.org/10.21608/EJCHEM.2020.33860.2707
V. Jatav, P. Mishra, S. Kashaw and J.P. Stables, Eur. J. Med. Chem., 43, 135 (2008); https://doi.org/10.1016/j.ejmech.2007.02.004
B. Kumaraswamy, K.T. Ranjith, S. Narasimha and R.N. Vasudeva, Int. J. Pharm. Pharm. Sci., 6, 572 (2014).
K.K. Jithendra, G.S. Krishnamurthy and K. Sunil, Int. J. Pharm. Pharm. Sci., 8, 134 (2016).
O. Bekircan, B. Kahveci and M. Kucuk, Turk. J. Chem., 30, 29 (2006).
O. Bekircan and H. Bektas, Molecules, 13, 2126 (2008); https://doi.org/10.3390/molecules13092126
B. Kahveci, O. Bekircan and S.A. Karaoglu, Indian J. Chem., 44B, 2614 (2005).
C. Park, J.-S. Lim, Y. Lee, B. Lee, S.-W. Kim, J. Lee and S. Kim, Enzyme Microb. Technol., 40, 1758 (2007); https://doi.org/10.1016/j.enzmictec.2006.12.005
N. Raman, L. Mitu, A. Sakthivel and M.S.S. Pandi, J. Iran. Chem. Soc., 6, 738 (2009).
M. Hernandes, S.M. Cavalcanti, D.R. Moreira, W. de Azevedo Junior and A.C. Leite, Curr. Drug Targets, 11, 303 (2010); https://doi.org/10.2174/138945010790711996
A. Casini, A. Scozzafava and A.C.T. Supuran, Expert Opin. Ther. Pat., 12, 1307 (2002); https://doi.org/10.1517/13543776.12.9.1307
C.T. Supuran, A. Scozzafava, L. Menabuoni, F. Mincione, F. Briganti and G. Mincione, Eur. J. Pharm. Sci., 8, 317 (1999); https://doi.org/10.1016/S0928-0987(99)00022-6
M. Remko and C.-W. von der Lieth, Bioorg. Med. Chem., 12, 5395 (2004); https://doi.org/10.1016/j.bmc.2004.07.049
A.K. Gadad, C.S. Mahajanshetti, S. Nimbalkar and A. Raichurkar, Eur. J. Med. Chem., 35, 853 (2000); https://doi.org/10.1016/S0223-5234(00)00166-5
G.H. Elgemeie, R.A. Azzam and R.E. Elsayed, Med. Chem. Res., 28, 1099 (2019); https://doi.org/10.1007/s00044-019-02378-6
B.R. Stranix, J.F. Lavallee, G. Sevigny, J. Yelle, V. Perron, N. LeBerre, D. Herbart and J.J. Wu, Bioorg. Med. Chem. Lett., 16, 3459 (2006); https://doi.org/10.1016/j.bmcl.2006.04.011
K. Sunitha, S. Nair and P. Palanisamy, Asian J. Chem., 34, 663 (2022); https://doi.org/10.14233/ajchem.2022.23591
P. Bernfeld, eds: S.P. Colowick and N.O. Kaplan, Amylase, a and b in Methods in Enzymology, Academic Press; New York, NY, USA, pp. 149-158 (1955).
M.C. Alley, D.A. Scudiero, A. Monks, M.L. Hursey, M.J. Czerwinski, D.L. Fine, B.J. Abbott, J.G. Mayo, R.H Shoemaker and M.R. Boyd, Cancer Res., 48, 589 (1988).
T. Mosmann, J. Immunol. Methods, 65, 55 (1983); https://doi.org/10.1016/0022-1759(83)90303-4