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. 2007 Aug 13;12(8):1805-16.
doi: 10.3390/12081805.

A study on 4-acylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones

Muzaffer Alkan  1 , Haydar Yüksek, Fatih Islamoğlu, Sule Bahçeci, Mustafa Calapoğlu, Mahfuz Elmastaş, Hüseyin Akşit, Mustafa Ozdemir
Affiliations

A study on 4-acylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones

Muzaffer Alkan et al. Molecules. .

Abstract

Five novel 3-alkyl-4-phenylacetylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones (2) were synthesized by the reactions of 3-alkyl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1) with phenylacetyl chloride and characterized by elemental analyses and IR, 1HNMR, 13C-NMR and UV spectral data. The newly synthesized compounds 2 were titrated potentiometrically with tetrabutylammonium hydroxide in four non-aqueous solvents such as isopropyl alcohol, tert-butyl alcohol, acetonitrile and N,N-dimethylformamide, and the half-neutralization potential values and the corresponding pKa values were determined for all cases. In addition, these new compounds and five recently reported 3-alkyl-4-(pmethoxybenzoylamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (3) were screened for their antioxidant activities.

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Figures

Scheme 1
Scheme 1
Figure 1
Figure 1
The change of the pKa values with the dielectric constant of the solvent.
Figure 2
Figure 2
The exchange of the pKa values with autoprotolysis constant.
Figure 3
Figure 3
Scavenging effect of compounds 2, 3, BHA and α-tocopherol at different concentrations (50-100-150 µg/mL).
Figure 4
Figure 4
Metal chelating effect of different amount of the compounds 2 and 3, BHT and α-tocopherol on ferrous ions.
See this image and copyright information in PMC

References

    1. 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. doi: 10.1080/00304949309457935. - DOI
    1. Ikizler A., Doğan 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.
    1. 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. - PubMed
    1. 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.
    1. Yüksek H., Ocak Z., Alkan M., Bahçeci Ş., Özdemir M. Synthesis and determination of pKa values of some new 3,4-disubstituted-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives in non-aqueous solvents. Molecules. 2004;9:232–240. - PMC - PubMed