Synthesis and Antioxidant Properties of Novel Quinazoline Derivatives

Zenta Tetere, Daina Zicāne, Irisa Rāviņa, Inese Mieriņa, Inese Rijkure

Abstract


Quinazoline derivatives have expressed a broad spectrum of biological activities, but there are few examples in literature on an antioxidant activity of different quinazolines. On the basis of literature by Chinese scientists on the effective antioxidant activity of Schiff bases containing 2-oxoquinoline and due to structural similarity of quinoline and quinazoline ring systems, the reactions of 3-aminoquinazolinone with a range of aromatic aldehydes and ethoxymethylene derivatives have been carried out and their radical scavenging activities have been studied.

Keywords:
3-amino-quinazolin-4(3H)-one, aldehydes, antioxidant activity, ethoxymethylene compounds, Schiff bases

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References


Rakhi, R., Abhinav, P. M. A Review on Biological Activity of Quinazolinones. International Journal of Pharmacy and Pharmaceutical Sciences, 2012, vol. 4, N 2, pp. 66-70.

Panneer Selvam, T., Nijayaraj Kumar, P., Siva Kumar, A. Synthesis and Anti-oxidant Activity of Novel 6,7,8,9-tetrahydro-5H-5-(2’-hydroxy phenyl)-2-(4’-substituted benzylidene)-3-(4-nitrophenylamino)triazolo quinazoline Derivatives. Research in Biotechnology, 2010, N 1, pp. 38-48.

Mohana Roopan, S., Nawaz Khan, F. Free Radical Scavenging Activity of Nitrogen Heterocyclics-quinazolinones and Tetrahydrocarbazolones. Indian Journal of Heterocyclic Chemistry, 2008, vol. 18, N 2, pp. 183-184.

Kovalenko, S., Belenichev, I., Galitsa, V., Krivoshey, O. Synthesis of 2-(3,4-dihydro-3-oxo-2H-[1,2,4]triazino[4,3-c]quinazolin-4-yl)acetic Acid Derivatives as Potential Antioxidants in Nitrosative Stress Model. Farmacia, 2010, vol. 58, N 2, pp. 145-157.

Zhang, Y., Fang, Y., Liang, H., et. al. Synthesis and Antioxidant Activities of 2-oxo-quinoline-3-carbaldehyde Schiff-base Derivatives. Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, N 1, pp. 107-111. http://dx.doi.org/10.1016/j.bmcl.2012.11.006

Shemchuk, L. A., Chernykh, V. P., Arzumanov, P. S. et al. Synthesis of N-(4-oxo-3,4-dihydroquinazolin-3-yl)succinimide and N-(4-oxoquinazolin-3-yl)succinamic Acid Derivatives Based Thereon. Russian Journal of Organic Chemistry, 2007, vol. 43, pp. 615-618. http://dx.doi.org/10.1134/S1070428007040215

Rāviņa, I., Tetere, Z., Zicāne, D. Metoksibenzolidēnamino-3, 4-dihidrohinazolinonu sintēze. Latvijas Ķīmijas žurnāls, 2009, Nr. 3, 231.-235.lpp.

Deepak Kumar, B., Rawat, D. S. Synthesis and Antioxidant Activity of Thymol and Carvacrol Based Schiff Bases. Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, N 3, pp. 641-645. http://dx.doi.org/10.1016/j.bmcl.2012.12.001

Sayed Alam, M., Choi, J.-H., Lee, D.-U. Synthesis of Novel Schiff Base Analogues of 4-Amino-1,5-dimethyl-2-phenylpyrazol-3-one and Their Evaluation for Antioxidant and Anti-inflammatory Activity. Bioorganic and Medicinal Chemistry, 2012, vol. 20, N 13, pp. 4103-4108. http://dx.doi.org/10.1016/j.bmc.2012.04.058

LeBlanc, L. M., Paré, A. F., Jean-François, J., et al. Synthesis and Antiradical/Antioxidant Activities of Caffeic Acid Phenethyl Ester and Its Related Propionic, Acetic, and Benzoic Acid Analogues. Molecules, 2012, vol. 17, pp. 14637-14650. http://dx.doi.org/10.3390/molecules171214637

Gülçin, I. Antioxidant Activity of Caffeic acid (3,4-dihydroxycinnamic acid). Toxicology, 2006, vol. 217, N 2-3, pp. 213-220. http://dx.doi.org/10.1016/j.tox.2005.09.011

Mieriņa, I., Tetere, Z., Zicāne, D. et al. Synthesis and Antioxidant Activity of New Analogs of Quin-C1. Chemistry of Heterocyclic Compounds, 2013, vol. 48, pp. 1824-1831. http://dx.doi.org/10.1007/s10593-013-1215-3




DOI: 10.7250/msac.2014.009

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