Design and Synthesis of 3-Triazolo-coumarins and Their Applications in Scavenging Radicals and Protecting DNA

doi:10.1007/s40242-015-5191-2

Abstract

Abstract:

In this study, we synthesized a series of 3-triazolo-coumarins and evaluated their antioxidant activities respectively by two methods: trapping 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical(ABTS^+·) and oxidation of DNA which was induced by Cu²⁺/glutathione(GSH), ·OH and 2,2'-azobis(2-amidinopropane hydrochloride)(AAPH). Among the nine 3-triazolo-coumarins, compounds 6c and 6f―6i were synthesized for the first time, which exhibited the capability of terminating radical propagation-chains in oxidation of DNA induced by AAPH. In this study, we found that phenethylamine moiety, hydroxyl and ortho-methoxy are the key groups to enhance the antioxidant activities of compounds.

Key words: 3-Triazolo-coumarin, Coumarin, Free radical, Oxidation, Antioxidant, DNA

LIU Zhihui, WANG Yingnan, SUN Jingbo, YANG Yang, LIU Qingwen, LIU Zaiqun, SONG Zhiguang. Design and Synthesis of 3-Triazolo-coumarins and Their Applications in Scavenging Radicals and Protecting DNA[J]. Chemical Research in Chinese Universities, 2015, 31(4): 526-533.

References

[1] Mena S., Ortega A. J. M., Estrela, Mutat. Res., 2009, 674, 36
[2] Cooke M. S., Evans M. D., Dizdaroglu M., Lunec J., FASEB J., 2003, 17, 1195
[3] Sugamura K., Keaney J. F. Jr., Free Radic. Biol. Med., 2011, 51, 978
[4] Xiao C., Luo X. Y., Li D. J., Lu H., Liu Z. Q., Song Z. G., Jin Y. H., Eur. J. Med. Chem., 2012, 53, 159
[5] Fraga C. G., Oteiza P. I., Free Radic. Biol. Med., 2011, 51, 813
[6] Liu Z. Q., Chem. Rev., 2010, 110, 5675
[7] Belluti F., Fontana G., Bo L. D., Carenini N., Giommarelli C., Zunino F., Bioorg. Med. Chem., 2010, 18, 3543
[8] Riveiro M. E., Moglioni A., Vazquez R., Gomez N., Facorro G., Piehl L., Celis E. R., Shayo C., Davio C., Bioorg. Med. Chem., 2008, 16, 2665
[9] Roussaki M., Kontogiorgis C. A., Hadjipavlou-Litina D., Hamilakis S., Detsi A., Bioorg. Med. Chem. Lett., 2010, 20, 3889
[10] Neichi T., Koshihara Y., Murota S., Biochim. Biophys. Acta, 1983, 753, 130
[11] Fylaktakidou K. C., Hadjipavlou-Litina D. J., Litinas K. E., Nicolaides D. N., Curr. Pharm. Des., 2004, 10, 3813
[12] Chimenti F., Bizzarri B., Bolasco A., Secci D., Chimenti P., Granese A., Carradori S., Rivanera D., Zicari A., Scaltrito M. M., Sisto F., Bioorg. Med. Chem. Lett., 2010, 20, 4922
[13] Kostova I., Curr. HIV Res., 2006, 4, 347
[14] Chilin A., Battistutta R., Bortolato A., Cozza G., Zanatta S., Poletto G., Mazzorana M., Zagotto G., Uriarte E., Guiotto A., Meggio F., Moro S., J. Med. Chem., 2008, 51, 752
[15] Peng S. Y., Wang L., Guo H. B., Sun S. F., Wang J., Org. Biomol. Chem., 2012, 10, 2537
[16] Huang Q., Zheng M., Yang S., Kuang C. X., Yua C., Yang Q., Eur. J. Med. Chem., 2011, 46, 5680
[17] Brik A., Muldoon J., Lin Y. C., Chem. Bio. Chem., 2003, 4, 1246
[18] Lee L. V., Mitchell M. L., Huang S. J., Fokin V. V., Sharpless K. B., Wong C., J. Am. Chem. Soc., 2003, 125, 9588
[19] Soto-Ortega D. D., Murphy B. P., Gonzalez-Velasquez F. J., Wilson K. A., Xie F., Wang Q., Moss M. A., Bioorg. Med. Chem., 2011, 192, 596
[20] Gao C. H., Shi X. Y., Hou X. T., Meng Q. F., Zhang Y. J., Teng L. R., Chem. Res. Chinese Universities, 2008, 24(4), 487
[21] Zhang P., Omaye S. T., Food Chem. Toxicol., 2001, 39, 239
[22] Reed C. J., Douglas K. T., Biochem. J., 1991, 275, 601
[23] Zhu B. Z., Kitrossky N., Chevion M., Biochem. Biophys. Res. Commun., 2000, 270, 942
[24] Re R., Pellegrini N., Proteggente A., Pannala A., Yang M., Rice-Evans C., Free Radical Biol. Med., 1999, 26, 1231
[25] Kolb H. C., Finn M. G., Sharpless K. B., Angew. Chem. Int. Ed., 2001, 40, 2004
[26] Kudale A. A., Kendall J., Warford C. C., Wilkins N. D., Bodwell G. J., Tetrahedron Letters, 2007, 48, 5077
[27] Vsevolod V., Rostovtsev L. G., Green V. V. F., Sharpless K. B., Angew. Chem. Int. Ed., 2002, 41, 2596
[28] Wei J. C., Guo-Wang P. Y., Cui L. G., Zhang H. B., Dai Y. F., Liu T. X., Chem. Res. Chinese Universities, 2014, 30(6), 1063
[29] Chen K. L., Zhao Y. H., Yuan X. Y., Chem. Res. Chinese Universities, 2014, 30(2), 339
[30] Zennaro L., Rossetto M., Vanzani P., Marco V. D., Scarpa M., Battistin L., Rigo A., Arch. Biochem. Biophys., 2007, 462, 38
[31] Li Y. F., Liu Z. Q., Luo X. Y., J. Agric. Food Chem., 2010, 58, 4126
[32] Li G. X., Liu Z. Q., J. Agric. Food Chem., 2009, 57, 3943
[33] Jain A., Alvi N. K., Parish J. H., Hadi S. M., Mutat. Res., 1996, 357, 83
[34] Janicek M. F., Haseltine W. A., Henner W. D., Nucleic Acids Res., 1985, 13, 9011
[35] Halliwell B., Trends Pharmacol. Sci., 2011, 32, 125
[36] Munoz-Munoz J. L., Garcia-Molina F., Varon R., Tudela J., García-Cánovas F., Rodriguez-Lopez J. N., J. Agric. Food Chem., 2010, 58, 2062
[37] Yim S. K., Yun S. J., Yun C. H., J. Biochem. Mol. Biol., 2004, 37, 629
[38] Wang R., Liu Z. Q., J. Org. Chem., 2012, 77, 3952