Preparation, GIAO NMR calculations and acidic properties of some novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives with their antioxidant activities

International Journal of Molecular Sciences

Volumn 9, Issue 1, 2008, Pages 12-32

  Yüksek, Haydar ^a   Alkan, Muzaffer ^a   Cakmak, Ismail ^a   Ocak, Zafer ^a   Bahçeci, Sule ^b   Calapǒlu, Mustafa ^a   Elmastas, Mahfuz ^c   Kolomuç, Ali ^b   Aksu, Havva ^a  

^a KAFKAS UNIVERSITY   (Turkey)

^b KARADENIZ TECHNICAL UNIVERSITY   (Turkey)

^c GAZIOSMANPASA UNIVERSITY   (Turkey)

Author keywords

4,5 Dihydro 1H 1,2,4 triazol 5 ones; Acylation; Antioxidant activity; Density functional calculations; GIAO; pK a; Potentiometric titrations

Indexed keywords

2 PROPANOL; ACETONE; ANTIOXIDANT; N,N DIMETHYLFORMAMIDE; TERT BUTYL ALCOHOL; TRIAZOLE DERIVATIVE;

ACIDITY; ANTIOXIDANT ACTIVITY; ARTICLE; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POTENTIOMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROSCOPY;

EID: 38949179431     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms9010012     Document Type: Article

References (51)

1. Ikizler, A.A.; Uçar, F.; Yüksek, H.; Aytin, A.; Yasa, I.; Gezer, T. Synthesis and antifungal activity of some new arylidenamino compounds. Acta Pol. Pharm.-Drug Res. 1997, 54, 135-140.
2. Yüksek, H.; Demibaş, A.; Ikizler, A.; Johansson, C.B.; Çelik, C.; Ikizler, A.A. Synthesis and antibacterial activities of some 4,5-dihydro-1H-1,2,4-triazol-5-ones. Arzneim.-Forsch./Drug Res. 1997, 47, 405-409.
3. Demirbaş, N.; Uǧurluoǧlu, R. Synthesis and antitumor activities of some 4-(1-naphthylidenamino)- and 4-(1-naphthylmethylamino)-1,2, 4-triazol-5-one derivatives. Turk J. Chem. 2004, 28, 679-690.
4. Alkan, M.; Yüksek, H.; İslamoǧlu, F.; Bahçeci, Ş.; Calapoǧlu, M.; Elmastaş, M.; Akşit, H.; Özdemir, M. A study on 4-acylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones. Molecules 2007, 12, 1805-1816.
5. Yüksek, H.; Kolayli, S.; Küçük, M.; Yüksek, M. O.; Ocak, U.; Şahinbaş, E.; Sivrikaya, E.; Ocak, M. Synthesis and andioxidant activities of some 4-benzylidenamino-4,5-dihydro-1H-1,2,4-triazol- 5-one derivatives. Indian J. Chem. 2006, 45B, 715-718.
6. Bhat, A.R.; Bhat, G.V.; Shenoy, G.G. Synthesis and in-vitro antimicrobial activity of new 1,2,4-triazoles. J. Pharm. Pharmacol. 2001, 53, 267-272.
7. Ikizler, A.; Doǧn, N.; Ikizler, A.A. The acylation of 4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones. Rev. Roum. Chim. 1998, 43, 741-746.
8. Ikizler, A.A.; Yüksek, H. Acetylation of 4-amino-4,5-dihydro-1H-1,2, 4-triazol-5-ones. Org. Prep. Proced. Int. 1993, 25, 99-105.
9. Yüksek, H.; Alkan, M.; Ocak, Z.; Bahçeci, Ş.; Ocak, M.; Özdemir, M. Synthesis and acidic properties of some new potential biologically active 4-acylamino-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Indian J. Chem. 2004, 43B, 1527-1531.
10. a values of some new 3,4-disubstituted-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives in nonaqueous solvents. Molecules 2004, 9, 232-240.
11. Bahçeci, Ş.; Yüksek, H.; Ocak, Z.; Azakli, A.; Alkan, M.; Ozdemir, M. Synthesis and potentiometric titrations of some new 4-(benzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives in non-aqueous media. Collect. Czech. Chem. Commun. 2002, 67, 1215-1222.
12. Bahçeci, Ş.; Yüksek, H.; Ocak, Z.; Köksal, C.; Ozdemir, M. Synthesis and non-aqueous medium titrations of some new 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Acta Chim. Slov. 2002, 49, 783-794.
13. Ikizler, A.A.; Ikizler, A.; Şentürk, H.B.; Serdar, M. The pKa values of some 1,2,4-triazole and 1,2,4-triazolin-5-one derivatives in nonaqueous media. Doǧa-Tr. Kimya D. 1988, 12, 57-66;
14. [Chem. Abstr. 1988, 109, 238277q].
15. a values of some 1,2,4-triazole derivatives in nonaqueous media. Doǧa-Tr. J. of Chem. 1991, 15, 345-354;
16. [Chem. Abstr. 1992, 116, 173458x].
17. Yüksek, H.; Ocak, Z.; Özdemir, M.; Ocak, M.; Bekar, M.; Aksoy, M. A study on novel 4-heteroarylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones. Indian J. Heterocy. Ch. 2003, 13, 49-52.
18. Yüksek, H.; Bahçeci, Ş.; Ocak, Z.; Alkan, M.; Ermiş, B.; Mutlu, T.; Ocak, M.; Özdemir, M. Synthesis of some 4,5-dihydro-1H-1,2,4-triazol-5-ones. Indian J. Heterocy. Ch. 2004, 13, 369-372.
19. Yüksek, H.; Üçüncü, O.; Alkan, M.; Ocak, Z.; Bahçeci, Ş.; Özdemir, M. Synthesis and nonaqueous medium titrations of some new 4-benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Molecules 2005, 10, 961-970.
20. Yüksek, H.; Bahçeci, Ş.; Ocak, Z.; Özdemir, M.; Ocak, M.; Ermis, B.; Mutlu, T. Synthesis and determination of acid dissociation constants of some new 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Asian J. Chem. 2005, 17, 195-201.
21. Schleyer, P.V.R.; Allinger, N.L.; Clark, T.; Gasteiger, J.; Kolmann, P.A. Schaefer, H.F.; Schreiner, P.R. In The encyclopedia of computational chemistry; John Wiley & Sons: Chichester, 1998.
22. Ditchfield, R. Self-consistent perturbation theory of diamagnetism. I A gauge-invariant LCAO method for N.M.R. chemical shifts. Mol. Phys. 1974, 27, 789-807.
23. 15N, and 1H NMR chemical shifts in aminopyrimidines and aminobenzenes: relationships to electron densities and amine group orientations. J. Am. Chem. Soc. 1977, 119, 8699-8711.
24. 15N NMR and GIAO CPHF calculations on two quinoacridinium salts. Magn. Reson. Chem. 2000, 38, 482-485.
25. Yüksek, H.; Gürsoy, Ö.; Çakmak, İ.; Alkan, M. Synthesis and GIAO NMR calculation for some new 4,5-dihydro-1H-1,2,4- triazol-5-one derivatives: comparison of theoretical and experimental 1H and 13C chemical shifts. Magn. Reson. Chem. 2005, 43, 585-587.
26. 13C chemical shifts. Int. J. Mol. Sci. 2005, 6, 219-229.
27. Hussain, H.H.; Babic, G.; Durst, T.; Wright, J.; Flueraru, M.; Chichirau, A.; Chepelev, L.L. Development of novel antioxidants: design, synthesis, and reactivity. J. Org. Chem. 2003, 68, 7023-7032.
28. McClements, J.; Decker, E.A. Lipid oxidation in oil water emulsions: Impact of molecular environment on chemical reactions in heterogeneous food system. J. Food Sci. 2000, 65, 1270-1282.
29. Ikizler, A.A.; Un, R. Reactions of ester ethoxycarbonylhydrazones with some amine type compounds. Chim. Acta Turc. 1979, 7, 269-290;
30. [Chem. Abstr. 1991, 94, 15645d].
31. Oyaizu, M. Studies on products of browning reaction prepared from glucosamine. Japan. Nutri. 1986, 44, 307-316.
32. Blois, M.S. Antioxidant determinations by the use of a stable free radical. Nature 1958, 26, 1199-1200.
33. Dinis, T.C.P.; Madeira, V.M.C.; Almeida, L.M. Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Arch. Biochem. Biophys. 1994, 315, 161-169.
34. Frisch M.J. et al. Gaussian 03, Revision C. 02; Gaussian, Inc.: Pittsburgh PA, 2003.
35. London F.J. Phys. Radium 1937, 8, 3974.
36. Hameka H.F. On the magnetic shielding in the hydrogen molecule. Mol. Phys. 1958, 1, 203-215.
37. Wolinski K.; Hilton K.J.F.; Pulay P. Efficient implementation of the Gauge-Independent Atomic Orbital Method for NMR chemical shift calculations. J. Am. Chem. Soc. 1990, 112, 8251-8260.
38. Womacott T.M.; Womacott R.J. Introductory Statistics; 5th Edition; John Wiley & Sons: New York, 1990.
39. Meir, S.; Kanner, J.; Akiri, B.; Hadas, S.P. Determination and involvement of aqueous reducing compounds in oxidative defense systems of various senescing leaves. J. Agri. Food. Chem. 1995, 43, 1813-1819.
40. Yildirim, A.; Mavi, A.; Kara, A.A. Determination of antioxidant and antimicrobial activities of Rumex crispus L. extracts. J. Agri. Food. Chem. 2001, 4083-4089.
41. - radical scavenging properties of some flavonoids and related phenolic compounds. Naunyn-Schmiedebergs Arch. Pharmacol. 1979, 308, R27.
42. Soares, J.R.; Dinis, T.C.P.; Cunha, A.P.; Ameida, L.M. Antioxidant activities of some extracts of Thymus zygis. Free Raical Res. 1997, 26, 469-478.
43. Duh, P.D.; Tu, Y.Y.; Yen, G.C. Antioxidant activity of water extract of Harng Jyur (Chyrsanthemum morifolium Ramat). Lebn. Wissen. Techno. 1999, 32, 269.
44. Yamaguchi, F.; Ariga, T.; Yoshimira, Y.; Nakazawa, H. Antioxidative and anti-glycation activity of garcinol from Garcinia indica fruit rind. J. Agri. Food. Chem. 2000, 48, 180-185.
45. Strlic, M.; Radovic, T.; Kolar, J.; Pihlar, B. Anti- and prooxidative properties of gallic acid in fenton-type systems. J. Agri. Food. Chem. 2002, 50, 6313-6317.
46. Finefrock, A.E.; Bush, A.I.; Doraiswamy, P.M. Current status of metals as therapeutic targets in Alzheimer's disease. J. Am. Geriatr. Soc. 2003, 51, 1143-1148.
47. Çaliş, I.; Hosny, M.; Khalifa, T.; Nishibe, S. Secoiridoids from Fraxinus angustifolia. Phytochemistry 1993, 33, 1453-1456.
48. Gordon, M.H. Food Antioxidants; Elsevier: London-New York, 1990; pp. 1-18.
49. Hargis, L.G. Analytical Chemistry Principles and Techniques; Prentice-Hall Inc.: New Jersey, 1988.
50. Ikizler, A.A.: İkizler A.; Yüksek H. 1H-NMR spectra of some 4,5-dihydro-1,2,4-triazol-5-ones. Magn. Reson. Chem. 1993, 31, 1088-1094.
51. Ikizler, A.A.; Yüksek H.; Bahçeci Ş. 1H-NMR spectra of some ditriazolyls and ditriazolylalkanes. Monatsh. Chem. 1992, 123, 191-198.