新型黄酮-Tr?ger’s碱类衍生物的合成及其生物活性（英文）
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摘要
通过多步反应合成了一系列类黄酮取代的Tr?ger’s base衍生物,测试了其对Hep G2肝癌细胞的抗癌活性和四种细菌(铜绿假单胞菌PAM1032、野生型金黄色葡萄球菌,野生型大肠杆菌和大肠杆菌-大肠杆菌NMD-1)的抗菌活性.实验结果表明,该系列中有两种化合物在1μg/mL下对金黄色葡萄球菌有很高的抑制率,有五种产物对Hep G2肝癌细胞的IC50值低于阳性对照紫杉醇(30.87?g/m L),表现出较高的抑制活性,显示了其在新药研发领域潜在的应用价值.
A series of flavonoid-substituted Tr?ger's base analogues were synthesized via multi-step reaction. Their anti-cancer activities on the HepG2 hepatocellular carcinoma cell and antibacterial activities on four bacterial(Pseudomonas aeruginosa PAM1032, wild type Staphylococcus aureus, wild type Escherichia coli and Escherichia.coli-NMD-1) were evaluated. Two compounds were screened out because of their high inhibitory rate on Staphylococcus aureus at 1 μg/m L. The IC50 values of five products on the HepG2(hepatocellular carcinoma cell) were lower than that of positive control paclitaxel(30.87 ?g/mL), displaying their high inhibitory activity. The results indicated their potential applications in new drug development.
A series of flavonoid-substituted Tr?ger's base analogues were synthesized via multi-step reaction. Their anti-cancer activities on the HepG2 hepatocellular carcinoma cell and antibacterial activities on four bacterial(Pseudomonas aeruginosa PAM1032, wild type Staphylococcus aureus, wild type Escherichia coli and Escherichia.coli-NMD-1) were evaluated. Two compounds were screened out because of their high inhibitory rate on Staphylococcus aureus at 1 μg/m L. The IC50 values of five products on the HepG2(hepatocellular carcinoma cell) were lower than that of positive control paclitaxel(30.87 ?g/mL), displaying their high inhibitory activity. The results indicated their potential applications in new drug development.
引文
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[2]Prelog, V.; Wieland, P. Helv. Chim. Acta 1944, 27, 1127.
[3]Spielman, M. A. J. Am. Chem. Soc. 1935, 57, 583.
[4]Wilen, S. H.; Qi, J. Z.; Williard, P. G. J. Org. Chem. 1991, 56, 485.
[5]Wilcox, C. S. Tetrahedron Lett. 1985, 26, 5749.
[6]Harmata, M.; Onrayanil, K.; Barnes, C. L. Supramol. Chem. 2006,18, 581.
[7]Sergeyev, S. Chim. Acta 2009, 92, 415.
[8]Dolensky, B.; Elguero, J.; Král, V.; Pardo, C.; Valík, M. Heterocycl.Chem. 2007, 93, 1.
[9]Yuan, C. X.; Xin, Q.; Liu, H. J.; Wang, L.; Jiang, M. H.; Tao, X. T.Sci. China Chem. 2011, 54, 587.
[10]Pardo, C.; Sesmilo, E.; Gutiérrez-Puebla, E.; Monge, A.; Elguero, J.J. Org. Chem. 2001, 66, 1607.
[11]Bailly, C.;Laine,W.; Demeunynck,M.; Lhomme, J. Biochem. Bioph. Res. Commun. 2000, 273, 681.
[12]Marrero-Morejon, J.; Pardillo-Fontdevila, E.; Fernandez-Benitez, S.Chem. Commun. 1999, 161.
[13]Veale,E.B.;Frimannsson,D.O.;Lawler,M.;Gunnlaugsson,T.Org. Lett. 2009, 11, 4040.
[14]Johnson,R.A.;Gorman,R.R.;Wnuk,R.J.;Crittenden,N.J.J.Med. Chem. 1993, 36, 3202.
[15]Blaser, H. U.; Jalett, H. P.; Lottenbach, W.; Studer, M. J. Am. Chem.Soc. 2000, 122, 12675.
[16]Taylor, L. P.; Grotewold, E. Plant Biol. 2005, 8, 317.
[17]Pier-Giorgio P. J. Nat. Prod. 2000, 63, 1035.
[18]Bravo, L. Nutr. Rev. 1998, 56, 317.
[19]Yang, C. S. Nutrition 1999, 15, 946.
[20]Sun, A. Y.; Simonyi, A.; Sun, G. Y. Free Radical Biol. Med. 2002,32, 314.
[21]Arts, I. C.; Hollman, P. C. J. Clin. Nutr. 2005, 81, 317S.
[22]Scalbert,A.;Manach,C.;Morand,C.;Remesy,C.;Jimenez,L.Crit. Rev. Food Sci. Nutr. 2005, 45, 287.
[23]Yuan, R.; Li, M. Q.; Xu, J. B.; Huang, S. Y.; Zhou, S. L.; Zhang, P.;Liu, J.-J.; Wu, H. Tetrahedron 2016, 72, 4081.
[24]Chu, Y. H.; Wan, Y.; Liu, Z. T.; Qiu, F.; Han, X. E.; Wu, H. Tetrahedron Lett. 2015, 56, 7046.
[25]Neogi,I.;Jhulki,S.;Ghosh,A.;Chow,T.J.;Moorthy,J.N.Org.Electron. 2014, 15, 3766.
[26]Solano,C.;Svensson,D.;Olomi,Z.;Jensen,J.;Wendt,O.F.;W?rnmark, K. Eur. J. Org. Chem. 2005, 16, 3510.
[27]Jensen, J.; Tejler, J.; Waernmark, K. J. Org. Chem. 2002, 67, 6008.
[28]Safavi,M.;Esmati,N.;Ardestani,S.K.;Emami,S.;Ajdari,S.;Davoodi, J.; Shafiee, A.; Foroumadi, A. Eur. J. Med.Chem. 2012,58, 573.
[29]Mai, C. W.; Yaeghoobi, M.; Abd-Rahman, N.; Kang, Y. B.; Pichika,M. R. Eur. J. Med. Chem. 2014, 77, 378.