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Vol. 35 No. 1 (2023): Vol 35 Issue 1

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Synthesis and Anticancer Activity of Novel Thiazolo-Coumarin Derivatives

https://doi.org/10.14233/ajchem.2023.27263
R. Swethan Babu
Department of Pharmaceutical Chemistry, SRM College of Pharmacy, SRM IST Kattankulathur, Kancheepuram-603203, India
Senthilkumar Palaniappan
Faculty of Pharmacy, Karpagam Academy of Higher Education, Pollachi Main Road, Eachanari Post, Coimbatore-641021, India
M.K. Kathiravan
Dr. A.P.J. Abdul Kalam Research Lab, SRM College of Pharmacy, SRM IST Kattankulathur, Kancheepuram-603203, India

Corresponding Author(s) : M.K. Kathiravan

drmkkathir@gmail.com

Asian Journal of Chemistry, Vol. 35 No. 1 (2023): Vol 35 Issue 1

Abstract

As a starting point for creating new inhibitor scaffolds, a molecular hybridization approach was applied in designing the novel molecules using coumarin-thiazole hybrids as mPGES-1 enzyme inhibitors. Thus, in present work, the novel thiazolo coumarin derivatives (8-35) were synthesized and characterized by 1H NMR, IR and ESI-MS spectra. All the synthesized molecules (8-35) were also investigated for their anticancer activity on MCF-7 (breast cancer), caco-2 (colon cancer), HeLa (Cervix cancer) cell lines. Studies revealed that compounds (8-14) and (22-28) showed inhibition (IC50) at different concentrations of 12.5, 50, 100 μg/mL and more than 100 μg/mL.

Keywords

Thiazole Coumarin Cancer mPGES-1 inhibitors Molecular hybridization
Swethan Babu, R., Palaniappan, S., & Kathiravan, M. (2022). Synthesis and Anticancer Activity of Novel Thiazolo-Coumarin Derivatives. Asian Journal of Chemistry, 35(1), 187–193. https://doi.org/10.14233/ajchem.2023.27263
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References
  1. M. Akram, M. Iqbal, M. Daniyal and A.U. Khan, Biol. Res., 50, 33 (2017); https://doi.org/10.1186/s40659-017-0140-9
  2. H. Sung, J. Ferlay, R.L. Siegel, M. Laversanne, I. Soerjomataram, A. Jemal and F. Bray, CA Cancer J. Clin., 71, 209 (2021); https://doi.org/10.3322/caac.21660
  3. R.L. Siegel, K.D. Miller, H.E. Fuchs and A. Jemal, CA Cancer J. Clin., 72, 7 (2022); https://doi.org/10.3322/caac.21708
  4. E. Ricciotti and G.A. FitzGerald, Arterioscler. Thromb. Vasc. Biol., 31, 986 (2011); https://doi.org/10.1161/ATVBAHA.110.207449
  5. M. Murakami, Y. Nakatani, T. Tanioka and I. Kudo, Prostaglandins Other Lipid Mediat., 68–69, 383 (2002); https://doi.org/10.1016/S0090-6980(02)00043-6
  6. G. O’Callaghan and A. Houston, Br. J. Pharmacol., 172, 5239 (2015); https://doi.org/10.1111/bph.13331
  7. S. Donnini, F. Finetti, E. Terzuoli, L. Bazzani and M. Ziche, Immunopathol. Dis. Therap., 5, 223 (2014); https://doi.org/10.1615/ForumImmunDisTher.2015014095
  8. B. Waltenberger, K. Wiechmann, J. Bauer, P. Markt, S. M Noha, G. Wolber, J.M. Rollinger, O. Werz, D. Schuster and H. Stuppner, J. Med. Chem., 54, 3163 (2011); https://doi.org/10.1021/jm101309g
  9. V. Comunanza, EBioMedicine, 33, 14 (2018); https://doi.org/10.1016/j.ebiom.2018.06.008
  10. A. Carneiro, M.J. Matos, E. Uriarte and L. Santana, Molecules, 26, 501 (2021); https://doi.org/10.3390/molecules26020501
  11. M.A. Gouda, M.A. Salem and M.H. Helal, Curr. Bioactive Comp., 16, 818 (2020); https://doi.org/10.2174/1573407215666190405154406
  12. F.G. Medina, J.G. Marrero, M. Macías-Alonso, M.C. González, I. CórdovaGuerrero, A.G. Teissier García and S. Osegueda-Robles, Nat. Prod. Rep., 32, 1472 (2015); https://doi.org/10.1039/C4NP00162A
  13. E.K. Akkol, Y. Genç, B. Karpuz, E. Sobarzo-Sánchez and R. Capasso, Cancers, 12, 1959 (2020); https://doi.org/10.3390/cancers12071959
  14. K.V. Sairam, B.M. Gurupadayya, R.S. Chandan, D.K. Nagesha and B. Vishwanathan, Curr. Drug Dev., 13, 186 (2016); https://doi.org/10.2174/1567201812666150702102800
  15. F. Annunziata, C. Pinna, S. Dallavalle, L. Tamborini and A. Pinto, Int. J. Mol. Sci., 21, 4618 (2020); https://doi.org/10.3390/ijms21134618.
  16. D. Feng, A. Zhang, Y. Yang and P. Yang, Arch. Pharm., 353, 1900380 (2020); https://doi.org/10.1002/ardp.201900380
  17. I. Fotopoulos and D. Hadjipavlou-Litina, Med. Chem., 16, 272 (2020); https://doi.org/10.2174/1573406415666190416121448
  18. X.F. Song, J. Fan, L. Liu, X.F. Liu and F. Gao, Arch. Pharm., 353, 2000025 (2020); https://doi.org/10.1002/ardp.202000025
  19. T. Al-Warhi, A. Sabt, E.B. Elkaeed and W.M. Eldehna, Bioorg. Chem., 103, 104163 (2020); https://doi.org/10.1016/j.bioorg.2020.104163
  20. A. Carneiro, M.J. Matos, E. Uriarte and L. Santana, Molecules, 26, 501 (2021); https://doi.org/10.3390/molecules26020501
  21. S. Nayak and S.L. Gaonkar, Mini Rev. Med. Chem., 19, 215 (2019); https://doi.org/10.2174/1389557518666180816112151
  22. M.T. Chhabria, S. Patel, P. Modi and P.S. Brahmkshatriya, Curr. Top. Med. Chem., 16, 2841 (2016); https://doi.org/10.2174/1568026616666160506130731
  23. A. Arshad, H. Osman, M.C. Bagley, C.K. Lam, S. Mohamad and A.S.M. Zahariluddin, Eur. J. Med. Chem., 46, 3788 (2011); https://doi.org/10.1016/j.ejmech.2011.05.044
  24. R.G. Kalkhambkar, G.M. Kulkarni, H. Shivkumar and R.N. Rao, Eur. J. Med. Chem., 42, 1272 (2007); https://doi.org/10.1016/j.ejmech.2007.01.023
  25. B.P. Mallikarjuna, B.S. Sastry, G.V. Suresh Kumar, Y. Rajendraprasad, S.M. Chandrashekar and K. Sathisha, Eur. J. Med. Chem., 44, 4739 (2009); https://doi.org/10.1016/j.ejmech.2009.06.008
  26. L. Shao, X. Zhou, Y. Hu, Z. Jin, J. Liu and J. Fang, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 36, 325 (2006); https://doi.org/10.1080/15533170600651405
  27. F. Chimenti, S. Carradori, D. Secci, A. Bolasco, P. Chimenti, A. Granese and B. Bizzarri, J. Heterocycl. Chem., 46, 575 (2009); https://doi.org/10.1002/jhet.110
  28. F. Annunziata, C. Pinna, S. Dallavalle, L. Tamborini and and A. Pinto, Int. J. Mol. Sci., 21, 4618 (2020); https://doi.org/10.3390/ijms21134618
  29. H. Singh, J.V. Singh, K. Bhagat, H.K. Gulati, M. Sanduja, N. Kumar, N. Kinarivala and S. Sharma, Bioorg. Med. Chem., 27, 3477 (2019); https://doi.org/10.1016/j.bmc.2019.06.033
  30. U. Salar, K.M. Khan, S. Chigurupati, S. Syed, S. Vijayabalan, A. Wadood, M. Riaz, M. Ghufran and S. Perveen, Med. Chem., 15, 87 (2019); https://doi.org/10.2174/1573406414666180903162243
  31. J. Das, P. Chen, D. Norris, R. Padmanabha, J. Lin, R. Moquin, Z. Shen, L.S. Cook, A.M. Doweyko, S. Pitt, S. Pang, D.R. Shen, Q. Fang, H.F. de Fex, K.W. McIntyre, D.J. Shuster, K.M. Gillooly, K. Behnia, G.L. Schieven, J. Wityak and J.C. Barrish, J. Med. Chem., 49, 6819 (2006); https://doi.org/10.1021/jm060727j
  32. A. Ayati, T. Oghabi Bakhshaiesh, S. Moghimi, R. Esmaeili, K. Majidzadeh-A, M. Safavi, L. Firoozpour, S. Emami and A. Foroumadi, Eur. J. Med. Chem., 155, 483 (2018); https://doi.org/10.1016/j.ejmech.2018.06.015
  33. P. Mutai, G. Breuzard, A. Pagano, D. Allegro, V. Peyrot and K. Chibale, Bioorg. Med. Chem., 25, 1652 (2017); https://doi.org/10.1016/j.bmc.2017.01.035
  34. T.S. Chitre, M.K. Kathiravan, K.G. Bothara, S.V. Bhandari and R.R. Jalnapurkar, Chem. Biol. Drug Design, 78, 826 (2011); https://doi.org/10.1111/j.1747-0285.2011.01200.x
  35. K.S. Jain, J.B. Bariwal, M.S. Phoujdar, M.A. Nagras, R.D. Amrutkar, M.K. Munde, R.S. Tamboli, S.A. Khedkar, N.C. Vidyasagar, R.H. Khiste, V.V. Dabholkar and M.K. Kathiravan, J. Heterocycl. Chem,, 46, 178 (2009); https://doi.org/10.1002/jhet.30
  36. N.S. Vyawahare, A.A. Hadambar, A.S. Chothe, R.R. Jalnapurkar, A.M. Bhandare and M.K. Kathiravan, J. Chem. Biol., 5, 35 (2012); https://doi.org/10.1007/s12154-011-0067-5
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