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Synthesis, Antiglycating and Antioxidant activities of Triazolo hexahydroquinazolines

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Abstract

Some 5-aryl-triazolo[4,3-a] hexahydro quinazoline derivatives (4a-4e & 5a-5e) were synthesized and evaluated for their in vitro antiglycation and antioxidant activities. Title compounds were found to have potent antiglycating activity than rutin in the range between 0.096 and 0.300 M.The compounds 4b and 5c were the most active ones among them. The tested compounds had shown potent to moderate antioxidant activity by DPPH assay than BHT except 5e (p-NO2 phenyl derivative). Among all, hydroxyl derivatives (4a-4e) are more potent than the corresponding thiols (5a-5e).

References

  1. Brownlee, M. Lilly Lecture 1993. Glycation and diabetic complications. Diabetes 1994, 43, 836-41.
  2. http://dx.doi.org/10.2337/diab.43.6.836 DOI: https://doi.org/10.2337/diab.43.6.836
  3. Peppa, M.; Uribarri, J.; Vlassara, H. Glucose, Advanced Glycation End Products, and Diabetes Complications: What Is New and What Works. Clin. Diabetes 2003, 21, 186-187.
  4. http://dx.doi.org/10.2337/diaclin.21.4.186 DOI: https://doi.org/10.2337/diaclin.21.4.186
  5. Monnier, V. M. Intervention against the Maillard reaction in vivo. Arch Biochem Biophys 2003, 419, 1-15.
  6. http://dx.doi.org/10.1016/j.abb.2003.08.014 DOI: https://doi.org/10.1016/j.abb.2003.08.014
  7. Vasan, S.; Foiles, P.; Founds, H. Therapeutic potential of breakers of advanced glycation end product-protein crosslinks. Arch Biochem Biophys 2003, 419, 89-96.
  8. http://dx.doi.org/10.1016/j.abb.2003.08.016 DOI: https://doi.org/10.1016/j.abb.2003.08.016
  9. Hunt, J. V.; Bottoms, M. A.; Mitchinson, M. J. Oxidative alterations in the experimental glycation model of diabetes mellitus are due to protein-glucose adduct oxidation. Some fundamental differences in proposed mechanisms of glucose oxidation and oxidant production. Biochem J 1993, 291 (Pt 2), 529-535. http://dx.doi.org/10.1042/bj2910529 DOI: https://doi.org/10.1042/bj2910529
  10. Ahmed, N. Advanced glycation endproducts--role in pathology of diabetic complications. Diabetes Res Clin Pract 2005, 67, 3-21.
  11. http://dx.doi.org/10.1016/j.diabres.2004.09.004 DOI: https://doi.org/10.1016/j.diabres.2004.09.004
  12. Ahmad, M. S.; Ahmed, N. Antiglycation properties of aged garlic extract: possible role in prevention of diabetic complications. J Nutr 2006, 136, 796S-799S. DOI: https://doi.org/10.1093/jn/136.3.796S
  13. Gugliucci, A. Glycation as the glucose link to diabetic complications. J Am Osteopath Assoc 2000, 100, 621-634.
  14. Singh, R.; Barden, A.; Mori, T.; Beilin, L. Advanced glycation end-products: a review. Diabetologia 2001, 44, 129-146.
  15. http://dx.doi.org/10.1007/s001250051591 DOI: https://doi.org/10.1007/s001250051591
  16. Alagarsamy, V.; Muthukumar, V.; Pavalarani, N.; Vasanthanathan, P.; Revathi, R.; Synthesis, analgesic and anti-inflammatory activities of some novel 2,3-disubstituted quinazolin-4(3H)-ones. Biol Pharm Bull 2003, 26, 557-559.
  17. http://dx.doi.org/10.1248/bpb.26.557 DOI: https://doi.org/10.1248/bpb.26.557
  18. Shetha, A.; Wijdan, I. A. Synthesis and characterization of new quinazoline-4(3H)-one Schiff bases. J Chem Pharm Res 2013, 5, 4245.
  19. Patel, N. B.; Patel, V. N.; Patel, H. R.; Shaikh, F. M.; Patel, J. C. Synthesis and microbial studies of (4-oxo-thiazolidinyl) sulfonamides bearing quinazolin-4(3H)ones. Acta Pol Pharm 2010, 67, 267275.
  20. Pati, B.; Banerjee, S. Quinazolines: an illustrated review. J Adv Pharm Edu & Res 2013, 3, 13651.
  21. Rudrapal, M.; De, B. Chemistry and biological importance of heterocyclic Schiff 's bases. Int Res J Pure & App Chem 2013, 3, 232249.
  22. http://dx.doi.org/10.9734/IRJPAC/2013/3996 DOI: https://doi.org/10.9734/IRJPAC/2013/3996
  23. Vagdevi, H. M .; Lokesh, M. R.; Gowdarshivannanavar, B. C. Synthesis and antioxidant activity of 3-substituted Schiff bases of quinazoline-2,4-diones. Int J Chem Tech Res 2012, 4, 15271533.
  24. Abid, O. H.; Ahmed, A. H. Synthesis and characterization of novel quinazoline derivatives via reaction of isatoic anhydride with schiff 's base. Int J App Nat Sci 2013, 2, 11-20.
  25. Krishnan, S. K.; Ganguly, S.; Veerasamy, R.; Jan, B. Synthesis, antiviral and cytotoxic investigation of 2-phenyl-3-substituted quinazolin-4(3H)-ones. Eur Rev Med Pharmacol Sci 2011, 15, 673681.
  26. Saravanan, G.; Pannerselvam, P.; Prakash, C. R. Synthesis, analgesic and anti-inflammatory screening of novel Schiff bases of 3-amino-2-methyl quinazoline 4-(3H)-one. Der Pharmacia Lettre 2010, 2, 216226. DOI: https://doi.org/10.4103/0110-5558.72426
  27. Fan, W. Q.; Katritzky, A. R. 1,2,3-Triazoles. In Comprehensive Heterocycle Chemistry II; Katritzky, A.R.; Rees, C. W.; Scriven, E.F.V.; Eds.; Pergamon Press: New York, NY, USA, 1996; 4, 1126.
  28. Biorn, A. C.; Cocklin, S.; Madani, N.; Si, Z.; Ivanovic, T.; Samanen, J.; Ryk, D. I. V.; Pantophlet, R.; Burton, D. R.; Freire, E.; Sodroski, J.; Chaiken, I. M. Mode of action for linear peptide inhibitors of HIV-1 gp120 interactions. Biochemistry 2004, 43, 19281938
  29. http://dx.doi.org/10.1021/bi035088i DOI: https://doi.org/10.1021/bi035088i
  30. Whiting, M.; Muldoon, J.; Lin, Y. C.; Silverman, S. M.; Lindstrom, W.; Olson, A. J.; Kolb, H. C.; Finn, M. G.; Sharpless, B. K.; Elder, J. H.; Fokin, V. V. Inhibitors of HIV-1 protease by using in situ click chemistry. Angew. Chem. Int. Ed. 2006, 45, 14351439
  31. http://dx.doi.org/10.1002/anie.200502161 DOI: https://doi.org/10.1002/anie.200502161
  32. Wang, Z. J.; Gao, Y.; Hou, Y. L.; Zhang, C.; Yu, S. J.; Bian, Q.; Li, Z. M.; Zhao, W. G. Design, synthesis, and fungicidal evaluation of a series of novel 5-methyl-1H-1,2,3-trizole-4-carboxyl amide and ester analogues. Eur. J. Med. Chem. 2014, 86, 8794.
  33. http://dx.doi.org/10.1016/j.ejmech.2014.08.029 DOI: https://doi.org/10.1016/j.ejmech.2014.08.029
  34. Brockunier, L. L.; Parmee, E. R.; Ok, H. O.; Candelore, M. R.; Cascieri, M. A.; Colwell, L. F.; Eng, L.; Feeney, W. P.; Forrest, M. J.; Hom, G. J.; MacIntyre, D. E.; Tota, L.; Wyvratt, M. J.; Fisher, M. H.; Weber, A. E. Human beta3-adrenergic receptor agonists containing 1,2,3-triazole substituted benzenesulfonamides. Bioorg. Med. Chem. Lett. 2000, 10, 21112114
  35. http://dx.doi.org/10.1016/S0960-894X(00)00422-4 DOI: https://doi.org/10.1016/S0960-894X(00)00422-4
  36. Pande, V.; Ramos, M. J. Structural basis for the GSK-3beta binding affinity and selectivity against CDK-2 of 1-(4-aminofurazan-3yl)-5-dialkylaminomethyl-1H-[1,2,3]triazole-4-carboxylic acid derivatives. Bioorg. Med. Chem. Lett. 2005, 15, 51295135.
  37. http://dx.doi.org/10.1016/j.bmcl.2005.08.077 DOI: https://doi.org/10.1016/j.bmcl.2005.08.077
  38. Olesen, P. H.; Srensen, A. R.; Urs, B.; Kurtzhals, P.; Bowler, A. N.; Ehrbar, U.; Hansen, B. F. Synthesis and in vitro characterization of 1-(4-Aminofurazan-3-yl)-5-dialkylamino-methyl-1H- [1,2,3]triazole-4-carboxylic acid derivatives. A new class of selective GSK-3 inhibitors. J. Med. Chem. 2003, 46, 33333341.
  39. http://dx.doi.org/10.1021/jm021095d DOI: https://doi.org/10.1021/jm021095d
  40. Krasinski, A.; Radic, Z.; Manetsch, R.; Raushel, J.; Taylor, P.; Sharpless, B. K.; Kolb, H. C. In situ selection of lead compounds by click chemistry: Target-guided optimization of aceylcholinesterase inhibitors. J. Am. Chem. Soc. 2005, 127, 66866692.
  41. http://dx.doi.org/10.1021/ja043031t DOI: https://doi.org/10.1021/ja043031t
  42. Mocharla, V. P.; Colasson, B.; Lee, L. V.; Roeper, S.; Sharpless, B. K.; Wong, C. H.; Kolb, H. C. In situ click chemistry: Enzyme-generated inhibitors of carbonic anhydrase II. Angew. Chem. Int. Ed. 2005, 44, 116120.
  43. http://dx.doi.org/10.1002/anie.200461580 DOI: https://doi.org/10.1002/anie.200461580
  44. Degenhardt, T. P.; Alderson, N. L.; Arrington, D. D.; Beattie, R. J.; Basgen, J. M.; Steffes, M. W.; Thorpe, S. R.; Baynes, J. W. Pyridoxamine inhibits early renal disease and dyslipidemia in the streptozotocin-diabetic rat. Kidney Int 2002, 61, 939-950.
  45. http://dx.doi.org/10.1046/j.1523-1755.2002.00207.x DOI: https://doi.org/10.1046/j.1523-1755.2002.00207.x
  46. Forbes, J. M.; Soulis, T.; Thallas, V.; Panagiotopoulos, S.; Long, D. M.; Vasan, S.; Wagle, D.; Jerums, G.; Cooper, M. E. Renoprotective effects of a novel inhibitor of advanced glycation. Diabetologia 2001, 44, 108-14.
  47. http://dx.doi.org/10.1007/s001250051587 DOI: https://doi.org/10.1007/s001250051587
  48. Lehman, T. D.; Ortwerth, B. J. Inhibitors of advanced glycation end product-associated protein cross-linking. Biochim Biophys Acta 2001, 1535, 110-119.
  49. http://dx.doi.org/10.1016/S0925-4439(00)00087-9 DOI: https://doi.org/10.1016/S0925-4439(00)00087-9
  50. Price, D. L.; Rhett, P. M.; Thorpe, S. R.; Baynes, J. W. Chelating activity of advanced glycation end-product inhibitors. J Biol Chem 2001, 276, 48967-48972.
  51. http://dx.doi.org/10.1074/jbc.M108196200 DOI: https://doi.org/10.1074/jbc.M108196200
  52. Nakagawa, T.; Yokozawa, T.; Terasawa, K.; Shu, S.; Juneja, L. R. Protective activity of green tea against free radical- and glucose-mediated protein damage. J Agric Food Chem 2002, 50, 2418-2422.
  53. http://dx.doi.org/10.1021/jf011339n DOI: https://doi.org/10.1021/jf011339n
  54. Braca, A.; Sortino, C.; Politi, M.; Morelli, I.; Mendez, J. Antioxidant activity of flavonoids from Licania licaniaeflora. J Ethnopharmacol 2002, 79, 379-381.
  55. http://dx.doi.org/10.1016/S0378-8741(01)00413-5 DOI: https://doi.org/10.1016/S0378-8741(01)00413-5
  56. Bors, W.; Saran, M.; Elstner, E. Screening for plant antioxidants. Modern Methods of Plant Analysis-Plant Toxin Analysis-New Series 1992, 13, 277-295.
  57. http://dx.doi.org/10.1007/978-3-662-02783-7_11 DOI: https://doi.org/10.1007/978-3-662-02783-7_11

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Kulandaivelu, U.; Challuri, S.; Reddy, R. A.; Periyasamy, G.; Boyapati, S. Synthesis, Antiglycating and Antioxidant Activities of Triazolo Hexahydroquinazolines. J Pharm Chem 2015, 2 (2), 6-11. https://doi.org/10.14805/jphchem.2015.art30.
Received
November 14, 2014
Published
July 28, 2015
Section
Research Articles
Pages
6-11

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