Issue

Vol. 36 No. 6 (2024): Vol 36 Issue 6, 2024

Copyright (c) 2024 Asmaa Harunani , Bryan Ching Seng Chua, Jack Seng Cheong, Jia Ying Chok, Nur Azizah Nadhirah Azni, Sangeetha a/p Santhiran, Wasmiya Shajahan, Xin Yan Lai, Vasudeva Rao Avupati

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and in vitro Biological Evaluation of a Series of Benzothiazole-Sulfonylurea Hybrids as Novel Class of α-Glucosidase Inhibitors

https://doi.org/10.14233/ajchem.2024.31558
Asmaa Harunani
Department of Biomedical Science, School of Health Sciences, IMU University (Formerly known as International Medical University), 126, Jalan Jalil Perkasa 19, Bukit Jalil, 57000 Kuala Lumpur, Malaysia
https://orcid.org/0009-0007-0551-4907
Bryan Ching Seng Chua
Department of Pharmaceutical Chemistry, School of Pharmacy, IMU University (Formerly known as International Medical University), 126, Jalan Jalil Perkasa 19, Bukit Jalil, 57000 Kuala Lumpur, Malaysia
https://orcid.org/0009-0003-5857-0823
Jack Seng Cheong
Department of Pharmaceutical Chemistry, School of Pharmacy, IMU University (Formerly known as International Medical University), 126, Jalan Jalil Perkasa 19, Bukit Jalil, 57000 Kuala Lumpur, Malaysia
https://orcid.org/0009-0007-7990-5505
Jia Ying Chok
Department of Pharmaceutical Chemistry, School of Pharmacy, IMU University (Formerly known as International Medical University), 126, Jalan Jalil Perkasa 19, Bukit Jalil, 57000 Kuala Lumpur, Malaysia
https://orcid.org/0009-0005-3444-4624
Nur Azizah Nadhirah Azni
Department of Biomedical Science, School of Health Sciences, IMU University (Formerly known as International Medical University), 126, Jalan Jalil Perkasa 19, Bukit Jalil, 57000 Kuala Lumpur, Malaysia
https://orcid.org/0009-0007-3757-7048
Sangeetha Santhiran
Department of Biomedical Science, School of Health Sciences, IMU University (Formerly known as International Medical University), 126, Jalan Jalil Perkasa 19, Bukit Jalil, 57000 Kuala Lumpur, Malaysia
https://orcid.org/0009-0001-6337-649X
Wasmiya Shajahan
Department of Biomedical Science, School of Health Sciences, IMU University (Formerly known as International Medical University), 126, Jalan Jalil Perkasa 19, Bukit Jalil, 57000 Kuala Lumpur, Malaysia
https://orcid.org/0009-0005-9314-4998
Xin Yan Lai
Department of Pharmaceutical Chemistry, School of Pharmacy, IMU University (Formerly known as International Medical University), 126, Jalan Jalil Perkasa 19, Bukit Jalil, 57000 Kuala Lumpur, Malaysia
https://orcid.org/0009-0000-8288-4484
Vasudeva Rao Avupati
Department of Pharmaceutical Chemistry, School of Pharmacy, IMU University (Formerly known as International Medical University), 126, Jalan Jalil Perkasa 19, Bukit Jalil, 57000 Kuala Lumpur, Malaysia
https://orcid.org/0000-0003-0899-513X

Corresponding Author(s) : Vasudeva Rao Avupati

vasudevaraoavupati@gmail.com

Asian Journal of Chemistry, Vol. 36 No. 6 (2024): Vol 36 Issue 6, 2024

Abstract

A series of benzothiazole-sulfonylurea hybrids (C1-C9) were synthesized and the molecular structures were characterized using physical (state, colour, melting point) and spectral (FT-IR, 1H NMR, 13C NMR and ESI-Mass) methods. All the compounds were screened for their bioactive potential as antidiabetic agents through α-glucosidase enzyme inhibitory properties at 100 µM concentration. The results were compared with a standard drug, voglibose. The bioassay results revealed that compound C2 was found to be the hit molecule that has exhibited a percentage enzyme inhibition of 49.10%, which is relatively better than that of voglibose at 37.75%. The observed activity is primarily due to the synergistic or addition potential of the pharmacophores benzothiazole and sulfonylurea hybridized into one molecule; the structural analogues of these pharmacophores were earlier reported as α-glucosidase inhibitors.

Keywords

Benzothiazole Sulfonylurea Benzothiazole-sulfonylurea hybrid α-Glucosidase inhibitor Voglibose
Harunani , A., Chua, B. C. S., Cheong, J. S., Chok, J. Y., Nadhirah Azni, N. A., Santhiran, S., … Avupati, V. R. (2024). Synthesis and in vitro Biological Evaluation of a Series of Benzothiazole-Sulfonylurea Hybrids as Novel Class of α-Glucosidase Inhibitors. Asian Journal of Chemistry, 36(6), 1429–1435. https://doi.org/10.14233/ajchem.2024.31558
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. https://idf.org/about-diabetes/diabetes-facts-figures/
  2. H. Kashtoh and K.-H. Baek, Plants, 11, 2722 (2022); https://doi.org/10.3390/plants11202722
  3. S. Banerjee, S. Payra and A. Saha, Curr. Organocatal., 4, 164 (2018); https://doi.org/10.2174/2213337205666180119143539
  4. M. Asif and M. Imran, Mini Rev. Org. Chem., 18, 1086 (2021); https://doi.org/10.2174/1570193X17999201127110214
  5. R.A. Azzam, R.R. Osman and G.H. Elgemeie, ACS Omega, 5, 1640 (2020); https://doi.org/10.1021/acsomega.9b03706
  6. C. Kaplan-Ozen, B. Tekiner-Gulbas, E. Foto, I. Yildiz, N. Diril, E. Aki and I. Yalcin, Med. Chem. Res., 22, 5798 (2013); https://doi.org/10.1007/s00044-013-0577-5
  7. D.-C. Liu, H.-J. Zhang, C.-M. Jin and Z.-S. Quan, Molecules, 21, 164 (2016); https://doi.org/10.3390/molecules21030164
  8. N. Herrera Cano, M.S. Ballari, A.G. Lopez and A.N. Santiago, J. Agric. Food Chem., 63, 3681 (2015); https://doi.org/10.1021/acs.jafc.5b00150
  9. M. Kumar, S.-M. Chung, G. Enkhtaivan, R.V. Patel, H.-S. Shin and B.M. Mistry, Int. J. Mol. Sci., 22, 2368 (2021); https://doi.org/10.3390/ijms22052368
  10. N. Maheshwari, C. Karthikeyan, S.V. Bhadada, A.K. Verma, C. Sahi, N.S.H.N. Moorthy and P. Trivedi, Bioorg. Chem., 92, 103221 (2019); https://doi.org/10.1016/j.bioorg.2019.103221
  11. A. J. Suresh, K. Bharathi, and P. R. Surya, J. Pharm. Chem. Bio. Sci., 5, 312 (2018).
  12. M. Taha, M. Arbin, N. Ahmat, S. Imran and F. Rahim, Bioorg. Chem., 77, 47 (2018); https://doi.org/10.1016/j.bioorg.2018.01.002
  13. S. Yatam, R. Gundla, S.S. Jadav, N. Pedavenkatagari, J. Chimakurthy, N. Rani and T. Kedam, J. Mol. Struct., 1159, 193 (2018); https://doi.org/10.1016/j.molstruc.2018.01.060
  14. S. Narva, S. Chitti, S. Amaroju, S. Goud, M. Alvala, D. Bhattacharjee, N. Jain and C.S.K. Venkata Gowri, J. Heterocycl. Chem., 56, 520 (2019); https://doi.org/10.1002/jhet.3427
  15. H.A. Bhuva and S.G. Kini, J. Mol. Graph. Model., 29, 32 (2010); https://doi.org/10.1016/j.jmgm.2010.04.003
  16. T.T. Tung, D.T.K. Oanh, P.T.P. Dung, T.M. Van Hue, S.H. Park, B.W. Han, Y. Kim, J.-T. Hong, S.-B. Han and N.-H. Nam, Med. Chem., 9, 1051 (2013); https://doi.org/10.2174/15734064113099990027
  17. A. Husain, D. Madhesia, M. Rashid, A. Ahmad and S.A. Khan, J. Enzyme Inhib. Med. Chem., 31, 1682 (2016); https://doi.org/10.3109/14756366.2015.1128425
  18. K. Harrouche, J.-F. Renard, N. Bouider, P. De Tullio, E. Goffin, P. Lebrun, G. Faury, B. Pirotte and S. Khelili, Eur. J. Med. Chem., 115, 352 (2016); https://doi.org/10.1016/j.ejmech.2016.03.028
  19. P. Kapse, R.V. Chikhale, M.R. Khan, S.M. Wabaidur and M.A. Islam, J. Mol. Struct., 1227, 129516 (2021); https://doi.org/10.1016/j.molstruc.2020.129516
  20. M. Yoshida, I. Hayakawa, N. Hayashi, T. Agatsuma, Y. Oda, F. Tanzawa, S. Iwasaki, K. Koyama, H. Furukawa, S. Kurakata and Y. Sugano, Bioorg. Med. Chem. Lett., 15, 3328 (2005); https://doi.org/10.1016/j.bmcl.2005.05.077
  21. S. Cao, R. Cao, X. Liu, X. Luo and W. Zhong, Molecules, 21, 876 (2016); https://doi.org/10.3390/molecules21070876
  22. N.R. Stokes, H.B. Thomaides-Brears, S. Barker, J.M. Bennett, J. Berry, I. Collins, L.G. Czaplewski, V. Gamble, P. Lancett, A. Logan, C.J. Lunniss, H. Peasley, S. Pommier, D. Price, C. Smee and D.J. Haydon, Antimicrob. Agents Chemother., 57, 5977 (2013); https://doi.org/10.1128/AAC.00719-13
  23. E. Simonova, M. Henselová and P. Zahradník, Plant Soil Environ., 51, 496 (2005); https://doi.org/10.17221/3623-PSE
  24. M. Gollapalli, M. Taha, M.T. Javid, N.B. Almandil, F. Rahim, A. Wadood, A. Mosaddik, M. Ibrahim, M.A. Alqahtani and Y.A. Bamarouf, Bioorg. Chem., 85, 33 (2019); https://doi.org/10.1016/j.bioorg.2018.12.021
  25. P. Gupta, H.L. Yadav, G. Garg, R.S. Pawar, U.K. Patil and P.K. Singour, Asian J. Res. Chem., 3, 47 (2010).
  26. M.A. Mahran, S. William, F. Ramzy and A.M. Sembel, Molecules, 12, 622 (2007); https://doi.org/10.3390/12030622
  27. M.V. Papadopoulou, W.D. Bloomer, H.S. Rosenzweig, M. Kaiser, E. Chatelain and J.-R. Ioset, Bioorg. Med. Chem., 21, 6600 (2013); https://doi.org/10.1016/j.bmc.2013.08.022
  28. E. Lee, Y. An, J. Kwon, K.I. Kim and R. Jeon, Bioorg. Med. Chem., 25, 3614 (2017); https://doi.org/10.1016/j.bmc.2017.04.004
  29. K. Bhagdev and S. Sarkar, Ann. Rom. Soc. Cell Biol., 10, 20269 (2021).
  30. M. Cui, Z. Li, R.-K. Tang and B. Liu, Bioorg. Med. Chem., 18, 2777 (2010); https://doi.org/10.1016/j.bmc.2010.02.002
  31. R. Paramashivappa, P.P. Kumar, P.V. Subba Rao and A. Srinivasa Rao, Bioorg. Med. Chem. Lett., 13, 657 (2003); https://doi.org/10.1016/S0960-894X(02)01006-5
  32. X.-H. Shi, Z. Wang, Y. Xia, T.-H. Ye, M. Deng, Y.-Z. Xu, Y.-Q. Wei and L.-T. Yu, Molecules, 17, 3933 (2012); https://doi.org/10.3390/molecules17043933
  33. M. Anzini, A. Chelini, A. Mancini, A. Cappelli, M. Frosini, L. Ricci, M. Valoti, J. Magistretti, L. Castelli, A. Giordani, F. Makovec and S. Vomero, J. Med. Chem., 53, 734 (2010); https://doi.org/10.1021/jm901375r
  34. L. Aitken, O. Benek, B.E. McKelvie, R.E. Hughes, L. Hroch, M. Schmidt, L.L. Major, L. Vinklarova, K. Kuca, T.K. Smith, K. Musilek and F.J. Gunn-Moore, Molecules, 24, 2757 (2019); https://doi.org/10.3390/molecules24152757
  35. W.E. Mehanna, T. Lu, B. Debnath, D.S. Lasheen, R.A.T. Serya, K.A. Abouzid and N. Neamati, ChemMedChem, 12, 1045 (2017); https://doi.org/10.1002/cmdc.201700229
  36. A. Fischer, C. Schmidt, S. Lachenicht, D. Grittner, M. Winkler, T. Wrobel, A. Rood, H. Lemoine, W. Frank and M. Braun, ChemMedChem, 5, 1749 (2010); https://doi.org/10.1002/cmdc.201000297
  37. W.-P. Hu, Y.-K. Chen, C.-C. Liao, H.-S. Yu, Y.-M. Tsai, S.-M. Huang, F.-Y. Tsai, H.-C. Shen, L.-S. Chang and J.-J. Wang, Bioorg. Med. Chem., 18, 6197 (2010); https://doi.org/10.1016/j.bmc.2010.04.082
  38. E.Y. Song, N. Kaur, M.-Y. Park, Y. Jin, K. Lee, G. Kim, K.Y. Lee, J.S. Yang, J.H. Shin, K.-Y. Nam, K.T. No and G. Han, Eur. J. Med. Chem., 43, 1519 (2008); https://doi.org/10.1016/j.ejmech.2007.10.008
  39. D. Gandhi, D.K. Agarwal, P. Kalal, A. Bhargava, D. Jangid and S. Agarwal, Phosphorus Sulfur Silicon Rel. Elem., 193, 840 (2018); https://doi.org/10.1080/10426507.2018.1514502
  40. B. Rajeeva, N. Srinivasulu and S.M. Shantakumar, E-J. Chem., 6, 775 (2009); https://doi.org/10.1155/2009/404596
  41. A. Ammazzalorso, A. Giancristofaro, A. D’Angelo, B.D. Filippis, M. Fantacuzzi, L. Giampietro, C. Maccallini and R. Amoroso, Bioorg. Med. Chem. Lett., 21, 4869 (2011); https://doi.org/10.1016/j.bmcl.2011.06.028
  42. J.A. Morales-Garcia, I.G. Salado, M. Sanz-San Cristobal, C. Gil, A. Pérez-Castillo, A. Martínez and D.I. Pérez, ACS Omega, 2, 5215 (2017); https://doi.org/10.1021/acsomega.7b00869
  43. T.L. Dadmal, K. Appalanaidu, R.M. Kumbhare, T. Mondal, M.J. Ramaiah and M.P. Bhadra, New J. Chem., 42, 15546 (2018); https://doi.org/10.1039/C8NJ01249K
  44. F. Shah, Y. Wu, J. Gut, Y. Pedduri, J. Legac, P.J. Rosenthal and M.A. Avery, MedChemComm, 2, 1201 (2011); https://doi.org/10.1039/c1md00129a
  45. Ü.D. Özkay, C. Kaya, U.A. Çevik and Ö.D. Can, Molecules, 22, 1490 (2017); https://doi.org/10.3390/molecules22091490
  46. G. Turan, D. Osmaniye, B.N. Saglik, U.A. Çevik, S. Levent, B.K. Çavusoglu, Ü.D. Özkay, Y. Özkay and Z.A. Kaplancikli, Phosphorus Sulfur Silicon Rel. Elem., 195, 491 (2020); https://doi.org/10.1080/10426507.2020.1722667
  47. M. Gjorgjieva, T. Tomašiè, M. Baranèokova, S. Katsamakas, J. Ilaš, P. Tammela, L.P. Mašiè and D. Kikelj, J. Med. Chem., 59, 8941 (2016); https://doi.org/10.1021/acs.jmedchem.6b00864
  48. B. Nagaraju, J. Kovvuri, C.G. Kumar, S.R. Routhu, M.A. Shareef, M. Kadagathur, P.R. Adiyala, S. Alavala, N. Nagesh and A. Kamal, Bioorg. Med. Chem., 27, 708 (2019); https://doi.org/10.1016/j.bmc.2019.01.011
  49. F. Rahim, T.M. Samreen, S.M. Saad, S. Perveen, M. Khan, M.T. Alam, K.M. Khan and M.I. Choudhary, J. Chem. Soc. Pak., 37, 157 (2015).
  50. R.V. Gadhave and B.S. Kuchekar, Res. J. Pharm. Technol., 13, 5661 (2020); https://doi.org/10.5958/0974-360X.2020.00986.5
  51. W. Nong, A. Zhao, J. Wei, H. Cheng, X. Luo and C. Lin, RSC Adv., 8, 6231 (2018); https://doi.org/10.1039/C7RA13397A
  52. D.E. Uehling, K.H. Donaldson, D.N. Deaton, C.E. Hyman, E.E. Sugg, D.G. Barrett, R.G. Hughes, B. Reitter, K.K. Adkison, M.E. Lancaster, F. Lee, R. Hart, M.A. Paulik, B.W. Sherman, T. True and C. Cowan, J. Med. Chem., 45, 567 (2002); https://doi.org/10.1021/jm0101500
  53. H. Zhang, Y. Zhang, G. Wu, J. Zhou, W. Huang and X. Hu, Bioorg. Med. Chem. Lett., 19, 1740 (2009); https://doi.org/10.1016/j.bmcl.2009.01.082
  54. S. Fukuen, M. Iwaki, A. Yasui, M. Makishima, M. Matsuda and I. Shimomura, J. Biol. Chem., 280, 23653 (2005); https://doi.org/10.1074/jbc.M412113200
  55. D.B.J. Ramudu, P.H. Babu, N. Venkateswarlu, T. Vijaya, S. Rasheed, C.N. Raju and P.V. Chalapathi, Indian J. Chem., 57B, 127 (2018).
  56. C. Gang, M.-Y. Wang, M.-Z. Wang, S.-H. Wang, Y.-H. Li, and Z.-M. Li, Chem. Res. Chinese Univ., 27, 62 (2011).
  57. J.D. Burch, J. Farand, J. Colucci, C. Sturino, Y. Ducharme, R.W. Friesen, J.-F. Lévesque, S. Gagné, M. Wrona, A.G. Therien, M.-C. Mathieu, D. Denis, E. Vigneault, D. Xu, P. Clark, S. Rowland and Y. Han, Bioorg. Med. Chem. Lett., 21, 1041 (2011); https://doi.org/10.1016/j.bmcl.2010.12.014
  58. M.M.C. Lo, H.R. Chobanian, O. Palyha, Y. Kan, T.M. Kelly, X.-M. Guan, M.L. Reitman, J. Dragovic, K.A. Lyons, R.P. Nargund and L.S. Lin, Bioorg. Med. Chem. Lett., 21, 2040 (2011); https://doi.org/10.1016/j.bmcl.2011.02.011
  59. M.P. Winters, C. Crysler, N. Subasinghe, D. Ryan, L. Leong, S. Zhao, R. Donatelli, E. Yurkow, M. Mazzulla, L. Boczon, C.L. Manthey, C. Molloy, H. Raymond, L. Murray, L. McAlonan and B. Tomczuk, Bioorg. Med. Chem. Lett., 18, 1926 (2008); https://doi.org/10.1016/j.bmcl.2008.01.127
  60. C. León, J. Rodrigues, N.G. de Domínguez, J. Charris, P.J. Rosenthal , J. Gut and J.N. Domínguez, Eur. J. Med. Chem., 42, 735 (2007); https://doi.org/10.1016/j.ejmech.2007.01.001
  61. M. Frezza, L. Soulère, S. Reverchon, N. Guiliani, C. Jerez, Y. Queneau and A. Doutheau, Bioorg. Med. Chem., 16, 3550 (2008); https://doi.org/10.1016/j.bmc.2008.02.023
  62. J. Hanson, J.M. Dogné, J. Ghiotto, A.L. Moray, B.T. Kinsella and B. Pirotte, J. Med. Chem., 50, 3928 (2007); https://doi.org/10.1021/jm070427h
  63. P. Nussbaumer, D. Geyl, A. Horvath, P. Lehr, B. Wolff and A. Billich, Bioorg. Med. Chem. Lett., 13, 3673 (2003); https://doi.org/10.1016/j.bmcl.2003.08.019
  64. E. Salamon, R. Mannhold, H. Weber, H. Lemoine and W. Frank, J. Med. Chem., 45, 1086 (2002); https://doi.org/10.1021/jm010999g
  65. M.J. Lee, J.A. Elberling and H.T. Nagasawa, J. Med. Chem., 35, 3641 (1992); https://doi.org/10.1021/jm00098a007
  66. F. Mohamadi, M.M. Spees and G.B. Grindey, J. Med. Chem., 35, 3012 (1992); https://doi.org/10.1021/jm00094a013
  67. S. Khelili, G. Leclerc, G. Faury and J. Verdetti, Bioorg. Med. Chem., 3, 495 (1995); https://doi.org/10.1016/0968-0896(95)00040-N
Read More
Author biographies is not available.
Statistic
Read Counter : 0 Download : 0