Yıl: 2018 Cilt: 42 Sayı: 3 Sayfa Aralığı: 808 - 825 Metin Dili: İngilizce DOI: 10.3906/kim-1709-34 İndeks Tarihi: 08-11-2020

The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products

Öz:
We report herein the first synthesis of biologically active natural bromophenols, namely 1-(2,3,6-tribromo-4,5-dihydroxybenzyl)pyrrolidin-2-one (2), 2RS-1-(2,3-dibromo-4,5-dihydroxybenzyl)-5-oxopyrrolidine-2-carboxylic acid(3), and 2RS-methyl 1-(2,3-dibromo-4,5-dihydroxybenzyl)-5-oxopyrrolidine-2-carboxylate (4), along with their differentderivatives (6 and 8–18). Among the synthesized compounds, 3, 4, and their derivatives (8 and 9) are yielded inracemic form. Radical scavenging assays of the synthesized molecules were investigated using various bioanalyticalantioxidant methods including 2,2’-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS • +) and 2,2-diphenyl-1-picrylhydrazyl (DPPH • ). In addition, the reducing power of the novel bromophenols was investigated by Cu 2+ –Cu + reducing, Fe 3+ –Fe 2+ reducing, and [Fe 3+ –(TPTZ) 2 ] 3+ –[Fe 2+ –(TPTZ) 2 ] 2+ reducing capacity and ferrous ions(Fe 2+) chelating abilities. The molecules demonstrated powerful antioxidant activities when compared to standardantioxidant compounds of α -tocopherol, trolox, butylated hydroxyanisole (BHA), and butylated hydroxytoluene (BHT).Moreover, novel bromophenols were tested against cholinergic enzymes including acetylcholinesterase (AChE) andbutyrylcholinesterase (BChE) enzymes in the last part of this study. The presented novel bromophenols showed Kivalues in the range of 2.60 ± 0.75–16.36 ± 2.67 nM against AChE and 13.10 ± 3.33–54.47 ± 13.53 nM against BChE.
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  • 1. Kurata, K.; Taniguchii, K.; Takashima, K.; Hayashi, I.; Suzuki, M. Phytochemistry. 1997, 45, 485-487.
  • 2. Duan, X. J.; Li, X. M.; Wang, B. G. J. Nat. Prod. 2007, 70, 1210-1213.
  • 3. Balaydın, H. T.; Gu¨l¸cin, I˙.; Menzek, A.; G¨oksu, S.; Sahin, E. J. Enzyme Inhib. Med. Chem. 2010, 25, 685-695.
  • 4 Çetinkaya, Y.; G¨o¸cer, H.; Menzek, A.; Gu¨l¸cin, I˙. Arch. Pharm. 2012, 345, 323-334.
  • 5. Choudhary, M.; Patel, R. N.; Rawat, S.P. J. Mol. Struc. 2014, 1070, 94-105.
  • 6. Bharti, S.; Choudhary, M.; Mohan, B.; Rawat, S. P.; Sharma, S. R.; Ahmad K. J. Mol. Struc. 2017, 1049, 846-861.
  • 7. Balaydın, H. T.; S¸entu¨rk, M.; G¨oksu, S.; Menzek, A. Eur. J. Med. Chem. 2012, 54, 423-428.
  • 8. C¸ etinkaya, Y.; G¨o¸cer, H.; Gu¨l¸cin, I˙.; Menzek, A. Arch. Pharm. 2014, 347, 354-359.
  • 9. Bozta¸s; M.; C¸ etinkaya, Y.; Topal, M.; Gu¨l¸cin, I˙.; Menzek, A.; S¸ahin, E.; Tan¸c, M.; Supuran, C. T. J. Med. Chem. 2015, 58, 640-650.
  • 10. Nar, M.; C¸ etinkaya, Y.; Gu¨l¸cin, I˙.; Menzek, A. J. Enzyme Inhib. Med. Chem. 2013, 28, 402-406.
  • 11. Artun¸c, T.; C¸ etinkaya, Y.; G¨o¸cer, H.; Gu¨l¸cin, I˙.; Menzek, A.; S¸ahin, E.; Supuran, C. T. Chem. Biol. Drug. Des. 2016, 87, 594-607.
  • 12. Bayrak, C¸ .; Taslimi, P.; Gu¨l¸cin, I˙.; Menzek, A. Bioorg. Chem. 2017, 72, 359-366.
  • 13. Gribble, G. W. Chem. Soc. Rev. 1999, 28, 335-346.
  • 14. Akbaba, Y.; Tu¨rke¸s, C.; Polat, L.; S¨o˘gu¨t, H.; S¸ahin, E.; G¨oksu, S.; Menzek, A.; Beydemir, S¸. J. Enzyme Inhib. Med. Chem. 2013, 28, 1073-1079.
  • 15. Balaydın, H. T.; Akbaba, Y.; Menzek, A.; S¸ahin, E.; G¨oksu, S. Arkivoc. 2009, XIV, 75-87.
  • 16. Choi, J. S.; Park, H. J.; Jung, H. A.; Chung, H. Y.; Jung, J. H.; Choi, W. C. J. Nat. Prod. 2000, 63, 1705-1706.
  • 17. Liu, X.; Li, X.; Gao, L.; Cui, C.; Li, C.; Li, J.; Wang, B. Chin. J. Oceanol. Limnol. 2011, 29, 686-690.
  • 18. Zhao, J.; Ma, M.; Wang, S.; Li, S.; Cao, P.; Yang, Y.; Lu, Y.; Shi, J.; Xu, N.; Fan, X.; et al. J. Nat. Prod. 2005, 68, 691-694.
  • 19. Li, K.; Li, X. M.; Gloer, J. B.; Wang, B. G. Food Chem. 2012, 135, 868-872.
  • 20. Balaydın, H. T.; S¸entu¨rk, M.; Menzek, A. Bioorg. Med. Chem. Lett. 2012, 22, 1352-1357.
  • 21. Gu¨l¸cin, I˙. Arch. Toxicol. 2012, 86, 345-391.
  • 22. Gu¨l¸cin, I˙.; Beydemir, S. Mini Rev. Med. Chem. 2013, 13, 408-430.
  • 23. G¨o¸cer, H.; Akıncıo˘glu, A.; O¨ zta¸skın, N.; G¨oksu, S.; Gu¨l¸cin, I˙. Arch. Pharm. 2013, 346, 783-792.
  • 24. G¨o¸cer, H.; Gu¨l¸cin, I˙. Int. J. Food Sci. Nutr. 2011, 62, 821-825.
  • 25. Gu¨l¸cin, I˙.; Topal, F.; C¸ akmak¸cı, R.; G¨oren, A. C.; Bilsel, M.; Erdo˘gan, U. J. Food Sci. 2011, 76, C585-C593.
  • 26. Bursal, E.; Gu¨l¸cin, I˙. Food. Res. Int. 2011, 44, 482-1489.
  • 27. Gu¨l¸cin, I˙.; Topal, F.; Oztu¨rk Sarikaya, S. B.; Bursal, E.; G¨oren, A. C.; Bilsel, M. Rec. Nat. Prod. 2011, 5, 158-175.
  • 28. K¨oksal, E.; Bursal, E.; Dikici, E.; Tozo˘glu, F.; Gu¨l¸cin, I˙. J. Med. Plants Res. 2011, 5, 217-222.
  • 29. Topal, F.; Topal, M.; G¨o¸cer, H.; Kalın, P.; Ko¸cyi˘git, U. M.; Gu¨l¸cin, I˙.; Alwasel, S. H. J. Enzyme Inhib. Med. Chem. 2016, 31, 674-683.
  • 30. Aksu, K.; Topal. F.; Gu¨l¸cin, I˙.; Tu¨mer, F.; G¨oksu, S. Arch. Pharm. 2015, 348, 446-455.
  • 31. G¨o¸cer, H.; Akıncıo˘glu, A.; O¨ zta¸skın, N.; G¨oksu, S.; Gu¨l¸cin, I˙. Arch. Pharm. 2013, 346, 783-792.
  • 32. Gu¨l¸cin, I˙.; Oktay, M.; Kire¸cci, E.; Ku¨frevio˘glu, O¨ . I˙. Food Chem. 2003, 83, 371-382.
  • 33. Gu¨l¸cin, I˙.; Ku¨frevio˘glu, O¨ . I˙.; Oktay, M.; Bu¨yu¨kokuro˘glu, M. E. J. Ethnopharmacol. 2004, 90, 205-215.
  • 34. Gu¨l¸cin, I˙.; Scozzafava, A.; Supuran, C. T.; Akıncıo˘glu, H.; Koksal, Z.; Turkan, F.; Alwasel, S. H. J. Enzyme Inhib. Med. Chem. 2016, 31, 1060-1066.
  • 35. G¨o¸cer, H.; Topal, F.; Topal, M.; Ku¨¸cu¨k, M.; Teke, D.; Gu¨l¸cin, I˙.; Alwasel, S. H.; Supuran, C. T. J. Enzyme Inhib. Med. Chem. 2016, 31, 441-447.
  • 36. O¨ zta¸skın, N.; Taslimi, P.; Mara¸s, A.; G¨oksu, S.; Gu¨l¸cin, I˙. Bioorg. Chem. 2017, 74, 104-114.
  • 37. Akıncıo˘glu, A.; Kocaman, E.; Akıncıo˘glu, H.; Salmas, R. E.; Durda˘gı, S.; Gu¨l¸cin, I˙.; Supuran, C. T.; G¨oksu, S. Bioorg. Chem. 2017, 74, 238-250.
  • 38. Aksu, K.; O¨ zgeris, B.; Taslimi, P.; Naderi, A.; Gu¨l¸cin, I.; G¨oksu, S. Arch. Pharm. 2016, 349, 944-954.
  • 39. Taslimi, P.; Sujayev, A.; Garibov, E.; Nazarov, N.; Huyut, Z.; Alwasel, S. H.; Gu¨l¸cin, I˙. J. Biochem. Mol. Toxicol. 2017, 31, e21897.
  • 40. Mun, J.; Smith, M. B. Synthetic Commun. 2007, 37, 813-819.
  • 41. Mori, T.; Bando, H.; Kanaiwa, Y.; Amiya, T.; Kurata, K. Chem. Pharm. Bull. 1983, 3, 1754-1756.
  • 42. Akbaba, Y.; Balaydin, H. T.; G¨oksu, S.; Sahin, E.; Menzek A. Helv. Chim. Acta. 2010, 93, 1127-1135.
  • 43. S¸ahin, E.; Balaydın, H. T.; G¨oksu S.; Menzek, A. Acta Crystallogr. 2010, E66, o3029.
  • 44. C¸ etinkaya, Y.; Menzek, A.; S¸ahin, E.; Balaydın, H. T. Tetrahedron 2011, 67, 3483-3489.
  • 45. Gu¨l¸cin, I˙.; Tel, A. Z.; Kirecci, E. Int. J. Food Propert. 2008, 11, 450-471.
  • 46. K¨ose, L. P.; Gu¨l¸cin. I˙.; G¨oren, A. C.; Namiesnik, J.; Martinez-Ayala, A. L.; Gorinstein, S. Ind. Crops Prod. 2015, 74, 712-721.
  • 47. Gu¨l¸cin, I˙.; Bursal, E.; S¸ehito˘glu, H. M.; Bilsel, M.; G¨oren, A. C. Food Chem Toxicol. 2010, 48, 2227-2238.
  • 48. O¨ zta¸skın, N.; C¸ etinkaya, Y.; Taslimi, P.; G¨oksu, S.; Gu¨l¸cin, I • . Bioorg. Chem. 2015, 60, 49-57.
  • 49. Gu¨l¸cin; I˙.; Elmasta¸s, M.; Aboul-Enein, H. Y. Arab. J. Chem. 2012, 5, 489-499.
  • 50. C¸ etinkaya, Y.; G¨o¸cer, H.; Menzek, A.; Gu¨l¸cin, I˙. Arch. Pharm. 2012, 345, 323-334.
  • 51. Gu¨l¸cin, I˙.; Beydemir, S.; Topal, F.; Gagua, N.; Bakuridze, A.; Bayram, R.; Gepdiremen, A. J. Enzyme Inhib. Med. Chem. 2012, 27, 587-594.
  • 52. Blois, M. S. Nature 1958, 181, 1199-1200.
  • 53. Gu¨l¸cin, I˙.; Huyut, Z.; Elmasta¸s, M.; Aboul-Enein, H. Y. Arab. J. Chem. 2010, 3, 43-53.
  • 54. Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. 1999, Free Radical Biol. Med. 26, 1231-1237.
  • 55. De Ferrari, G.V.; Canales, M. A.; Shin, I.; Weiner, L. M.; Silman, I.; Inestrosa, N. C.; Biochemistry 2001, 40, 10447-10457.
  • 56. Cacabelos, R. Neuropsychiatr. Dis. Treat. 2007, 3, 303-333.
  • 57. Kamal, A.; Shaik, A. B.; Reddy, G. N.; Kumar, G. N.; Joseph, J.; Kumar, G. B.; Purushotham, U.; Sastry, G. N. Med. Chem. Res. 2014, 23, 2080-2092.
  • 58. Sugimoto, H.; Yamanishi, Y.; Iimura, Y.; Kawakami, Y. Curr. Med. Chem. 2000, 7, 303-333.
  • 59. Kaya, O¨ .; S¸engu¨l, M. E.; Menzek, A.; S¸ahin, E.; Gu¨r, B. Tetrahedron 2016, 72, 2828-2837.
  • 60. Velio˘glu, Y. S.; Mazza, G.; Gao, L.; Oomah, B. D. J. Agric. Food Chem. 1998, 46, 4113-4117.
  • 61. Yen, G. C.; Hung, C. Y. Food Res. Int. 2000, 33, 487-492.
  • 62. Apak, R.; Gu¸clu, K.; O¨ zyurek, M.; Karademir, S. E.; Er¸ca, E. Int. J. Food Sci. Nutr. 2006, 57, 292-304.
  • 63. Apak, R.; Gu¸clu, K.; O¨ zyurek, M.; Karademir, S.E. J. Agric. Food Chem. 2004, 52, 7970-7981.
  • 64. Benzie, I. F. F.; Strain, J. J. Anal. Biochem. 1996, 239, 70-76.
  • 65. Brand-Williams, W.; Cuvelier, M. E.; Berset, C. Lebensm. Wiss. Technol. 1995, 28, 25-30.
  • 66. Bondet, V.; Brand-Williams, W.; Berset, C. Food Sci. Technol. 1997, 30, 609-615.
  • 67. Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Free Radical Biol. Med. 1999, 26, 1231-1237.
  • 68. Dinis, T. C.; Maderia, V. M.; Almeida, L. M. Arch. Biochem. Biophys. 1994, 315, 161-169.
  • 69. Ellman, G. L.; Courtney, K. D.; Andres, V.; Featherston, R. M. Biochem. Pharmacol. 1961, 7, 88-95.
  • 70. O¨ zbey, F.; Taslimi, P.; Gu¨lcin, I˙.; Mara¸s, A.; G¨oksu, S.; Supuran, C. T. J. Enzyme Inhib. Med. Chem. 2016, 31, 79-85.
APA REZAI M, bayrak ç, TASLIMI P, Gulcin i, MENZEK A (2018). The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products. , 808 - 825. 10.3906/kim-1709-34
Chicago REZAI Mohsen,bayrak çetin,TASLIMI Parham,Gulcin ilhami,MENZEK Abdullah The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products. (2018): 808 - 825. 10.3906/kim-1709-34
MLA REZAI Mohsen,bayrak çetin,TASLIMI Parham,Gulcin ilhami,MENZEK Abdullah The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products. , 2018, ss.808 - 825. 10.3906/kim-1709-34
AMA REZAI M,bayrak ç,TASLIMI P,Gulcin i,MENZEK A The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products. . 2018; 808 - 825. 10.3906/kim-1709-34
Vancouver REZAI M,bayrak ç,TASLIMI P,Gulcin i,MENZEK A The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products. . 2018; 808 - 825. 10.3906/kim-1709-34
IEEE REZAI M,bayrak ç,TASLIMI P,Gulcin i,MENZEK A "The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products." , ss.808 - 825, 2018. 10.3906/kim-1709-34
ISNAD REZAI, Mohsen vd. "The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products". (2018), 808-825. https://doi.org/10.3906/kim-1709-34
APA REZAI M, bayrak ç, TASLIMI P, Gulcin i, MENZEK A (2018). The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products. Turkish Journal of Chemistry, 42(3), 808 - 825. 10.3906/kim-1709-34
Chicago REZAI Mohsen,bayrak çetin,TASLIMI Parham,Gulcin ilhami,MENZEK Abdullah The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products. Turkish Journal of Chemistry 42, no.3 (2018): 808 - 825. 10.3906/kim-1709-34
MLA REZAI Mohsen,bayrak çetin,TASLIMI Parham,Gulcin ilhami,MENZEK Abdullah The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products. Turkish Journal of Chemistry, vol.42, no.3, 2018, ss.808 - 825. 10.3906/kim-1709-34
AMA REZAI M,bayrak ç,TASLIMI P,Gulcin i,MENZEK A The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products. Turkish Journal of Chemistry. 2018; 42(3): 808 - 825. 10.3906/kim-1709-34
Vancouver REZAI M,bayrak ç,TASLIMI P,Gulcin i,MENZEK A The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products. Turkish Journal of Chemistry. 2018; 42(3): 808 - 825. 10.3906/kim-1709-34
IEEE REZAI M,bayrak ç,TASLIMI P,Gulcin i,MENZEK A "The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products." Turkish Journal of Chemistry, 42, ss.808 - 825, 2018. 10.3906/kim-1709-34
ISNAD REZAI, Mohsen vd. "The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products". Turkish Journal of Chemistry 42/3 (2018), 808-825. https://doi.org/10.3906/kim-1709-34