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Synthesis and Evaluation of α-Glucosidase and Pancreatic Lipase Inhibition by Quinazolinone-Coumarin Hybrids

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Chemistry of Heterocyclic Compounds Aims and scope

A new series of 2-substituted quinazolin-4(3H)-one derivatives including coumarin nucleus has been synthesized and screened for their lipase and α-glucosidase inhibition properties. Among the synthesized compounds, N'-{2-[2-(3,4-dichlorobenzyl)-4-oxoquinazolin-3(4H)-yl]acetyl}-2-oxo-2H-chromene-3-carbohydrazide and N'-{2-[2-(4-bromobenzyl)-4-oxoquinazolin-3(4H)-yl]acetyl}-2-oxo-2H-chromene-3-carbohydrazide showed the best inhibitory effect against α-glucosidase with IC50 values of 6.11 ± 0.40 and 7.34 ± 0.37 μM,respectively. These compounds also showed strong anti-lipase activity (IC50 3.52 ± 0.49 and 2.85 ± 0.27 μM, respectively).

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References

  1. Kumakura, S.; Onoda, K.; Hirose, M. J. Infect. Chemother. 2014, 20, 194.

    Article  Google Scholar 

  2. Hirose, M.; Ando, T.; Shofiqur, R.; Umeda, K.; Kodama, Y.; Nguyen, S. V.; Goto, T.; Shimada, M.; Nagaoka, S. Nutr. Metab. 2013, 10, 70.

    Article  Google Scholar 

  3. Mukherjee, M. J. Mol. Catal. B: Enzym. 2003, 22, 369.

    Article  CAS  Google Scholar 

  4. Birari, R. B.; Bhutani, K. K. Drug Discovery Today 2007, 12, 879.

    Article  CAS  Google Scholar 

  5. Ballinger, A.; Peikin, S. R. Eur. J. Pharmacol. 2002, 440, 109.

    Article  CAS  Google Scholar 

  6. Filippatos, T. D.; Derdemezis, C. S.; Gazi, I. F.; Nakou, E. S.; Mikhailidis, D. P.; Elisaf, M. S. Drug Saf. 2008, 31, 53.

    Article  CAS  Google Scholar 

  7. Wang, Q. Q.; Cheng, N.; Yi, W. B.; Peng, S. M.; Zou, X. Q. Bioorg. Med. Chem. 2014, 22, 1515.

    Article  CAS  Google Scholar 

  8. Casirola, D. M.; Ferraris, R. P. Metabolism 2006, 55, 832.

    Article  CAS  Google Scholar 

  9. Panahi, F.; Yousefi, R.; Mehraban, M. H.; Khalafi-Nezhad, A. Carbohydr. Res. 2013, 380, 81.

    Article  CAS  Google Scholar 

  10. King, H.; Rewers, M. Diabetes Care 1993, 16, 157.

    Article  CAS  Google Scholar 

  11. Alapati, V.; Noolvi, M. N.; Manjula, S. N.; Pallavi, K. J.; Patel, H. M.; Tippeswamy, B. S.; Satyanarayana, S. V. Eur. Rev. Med. Pharmacol. Sci. 2012, 16, 1753.

    CAS  Google Scholar 

  12. Widemann, B. C.; Balis, F. M.; Godwin, K. S.; McCully, C.; Adamson, P. C. Cancer Chemother. Pharmacol. 1999, 44, 439.

    Article  CAS  Google Scholar 

  13. Kobayashi, Y.; Nakano, Y.; Kizaki, M.; Hoshikuma, K.; Yokoo, Y.; Kamiya, T. Planta Med. 2001, 67, 628.

    Article  CAS  Google Scholar 

  14. Clissold, S. P.; Beresford, R.; Proquazone, A. Drugs 1987, 33, 478.

    Article  CAS  Google Scholar 

  15. Khadka, D. B.; Tran, G. H.; Shin, S.; Nguyen, H. T.; Cao, H. T.; Zhao, C.; Jin, Y.; Van, H. T.; Chau, M. V.; Kwon, Y.; Le, T. N.; Cho, W. J. Eur. J. Med. Chem. 2015, 103, 69.

  16. Rakesh, K. P.; Manukumar, H. M.; Gowda, D. C. Bioorg. Med. Chem. Lett. 2015, 25, 1072.

    Article  CAS  Google Scholar 

  17. Kayser, O.; Kolodziej, H. Planta Med. 1997, 63, 508.

    Article  CAS  Google Scholar 

  18. Hoult, J. R.; Paya, M. Gen. Pharmacol. 1996, 27, 713.

    Article  CAS  Google Scholar 

  19. Zaha, A. A.; Hazem, A. New Microbiol. 2002, 25, 213.

    CAS  Google Scholar 

  20. Kontogiorgis, C.; Hadjipavlou-Litina, D. J. Enzyme Inhib. Med. Chem. 2003, 18, 63.

    Article  CAS  Google Scholar 

  21. Khode, S.; Maddi, V.; Aragade, P.; Palkar, M.; Ronad, P. K.; Mamledesai, S.; Thippeswamy, A. H. M.; Satyanarayana, D. Eur. J. Med. Chem. 2009, 44, 1682.

    Article  CAS  Google Scholar 

  22. Kontogiorgis, C. A.; Hadjipavlou-Litina, D. J. J. Med. Chem. 2005, 48, 6400.

    Article  CAS  Google Scholar 

  23. Wang, C. J.; Hsieh, Y. J.; Chu, C. Y.; Lin, Y. L.; Tseng, T. H. Cancer Lett. 2002, 183, 163.

    Article  CAS  Google Scholar 

  24. Kostova, I. Mini-Rev. Med. Chem. 2006, 6, 365.

    Article  CAS  Google Scholar 

  25. Chimichi, S.; Boccalini, M.; Cosimelli, B.; Viola, G.; Vedaldi, D.; Dall'Acqua, F. Tetrahedron Lett. 2002, 43, 7473.

    Article  CAS  Google Scholar 

  26. Gouda, M. A.; Berghot, M. A.; Baz, E. A.; Hamama, W. S. Med. Chem. Res. 2012, 21, 1062.

    Article  CAS  Google Scholar 

  27. Khan, K. M.; Rahim, F.; Wadood, A.; Kosar, N.; Taha, M.; Lalani, S.; Khan, A.; Fakhri, M. I.; Junaid, M.; Rehman, W.; Khan, M.; Perveen, S.; Sajid, M.; Choudhary, M. I. Eur. J. Med. Chem. 2014, 81, 245.

    Article  CAS  Google Scholar 

  28. Wang, S. J.; Yan, J. F.; Wang, X. Y.; Yang, Z.; Lin, F. W.; Zhang, T. J. Eur. J. Med. Chem. 2010, 45, 1250.

  29. Islam, M. N.; Jung, H. A.; Sohn, H. S.; Kim, H. M.; Choi, J. S. Arch. Pharm. Res. 2013, 36, 542.

    Article  Google Scholar 

  30. Shen, Q.; Shao, J.; Peng, Q.; Zhang, W.; Ma, L.; Chan, A. S. C.; Gu, L. J. Med. Chem. 2010, 53, 8252.

    Article  CAS  Google Scholar 

  31. Kahveci, B.; Yılmaz, F.; Menteşe, E.; Ülker, S. Chem. Heterocycl. Compd. 2015, 51, 447. [Khim. Geterotsikl. Soedin. 2015, 51, 447.]

  32. Kahveci, B. Molecules 2005, 10, 376.

    Article  CAS  Google Scholar 

  33. Kahveci, B.; Ikizler, A. A. Turk. J. Chem. 2000, 24, 343.

    CAS  Google Scholar 

  34. Thati, B.; Noble, A.; Rowan, R.; Creaven, B. S.; Walsh, M.; McCann, M.; Egan, D.; Kavanagh, K. Toxicol. In Vitro 2007, 21, 801.

    Article  CAS  Google Scholar 

  35. Katritzky, A. R.; Narindoshvili, T.; Angrish, P. Synthesis 2008, 13, 2013.

    Article  Google Scholar 

  36. Chandrika, P. M.; Yakaiah, T.; Rao, A. R. R.; Narsaiah, B.; Reddy, N. C.; Sridhar, V.; Rao, J. V. Eur. J. Med. Chem. 2008, 43, 846.

    Article  CAS  Google Scholar 

  37. Grover, G.; Kini, S. G. Eur. J. Med. Chem. 2006, 41, 256.

    Article  CAS  Google Scholar 

  38. Casagrande, M.; Barteselli, A.; Basilico, N.; Parapini, S.; Taramelli, D.; Sparatore, A. Bioorg. Med. Chem. 2012, 20, 5965.

    Article  CAS  Google Scholar 

  39. Kashaw, S. K.; Kashaw, V.; Mishra, P.; Jain, N. K.; Stables, J. P. Eur. J. Med. Chem. 2009, 44, 4335.

    Article  CAS  Google Scholar 

  40. Decker, M. Eur. J. Med. Chem. 2005, 40, 305.

    Article  CAS  Google Scholar 

  41. Shen, Y.; Han, C.; Cai, S. Y.; Lu, P.; Wang, Y. G. Tetrahedron Lett. 2012, 53, 5671.

    Article  CAS  Google Scholar 

  42. Choudhary, M. I.; Adhikari, A.; Rasheed, S.; Marasini, B. P.; Hussain, N.; Kaleem, W. A. Phytochem. Lett. 2011, 4, 404.

    Article  CAS  Google Scholar 

  43. Kurihara, H.; Asami, S.; Shibata, H.; Fukami, H.; Tanaka, T. Biol. Pharm. Bull. 2003, 26, 383.

    Article  CAS  Google Scholar 

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This work was supported by the Scientific and Technological Research Council of Turkey (TUBITAK) under the project number of 115Z885. The authors gratefully thank TUBITAK for financial support.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Art and Sciences, Recep Tayyip Erdogan University, Fener St., 53100, Rize, Turkey

    Emre Menteşe, Nesrin Karaali, Gülay Akyüz & Fatih Yılmaz

  2. Department of Biology, Faculty of Art and Sciences, Recep Tayyip Erdogan University, Fener St., 53100, Rize, Turkey

    Serdar Ülker

  3. Department of Nutrition and Dietetics, Faculty of Health Sciences, Karadeniz Technical University, Farabi St., 61080, Trabzon, Turkey

    Bahittin Kahveci

Authors
  1. Emre Menteşe
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  2. Nesrin Karaali
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  4. Fatih Yılmaz
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  5. Serdar Ülker
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  6. Bahittin Kahveci
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Correspondence to Emre Menteşe.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(12), 1017–1024

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Menteşe, E., Karaali, N., Akyüz, G. et al. Synthesis and Evaluation of α-Glucosidase and Pancreatic Lipase Inhibition by Quinazolinone-Coumarin Hybrids. Chem Heterocycl Comp 52, 1017–1024 (2016). https://doi.org/10.1007/s10593-017-2002-3

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  • DOI: https://doi.org/10.1007/s10593-017-2002-3

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