Journal of Pharmaceutical and Biomedical Sciences

A Method for Highly Synthetic Benzofuran Ring

Jilin Fan, Yiqun Chang, Jinsong Hou, Miaoqi Huang, Jingyuan Liu, Sijun Chen, Jialiang Guo, Pinghua Sun

Abstract


Presently, a series of natural products – Houttuynoids – were isolated from Houttuynia, which exhibited promising anti-virus activity. As the amount of natural Houttuynoids from Houttuynia is rare, it is hard to separate and extract from Houttuynia. The synthesis of Houttuynoid B was completed based on the previous research and, the benzofuran ring is a key intermediate for the synthesis of Houttuynoid B. However, the yield is low in his synthesis route. We have studied the synthesis of this benzofuran ring intermediate. Our route has greatly improved its synthetic yield. Their structures were characterized by 1H NMR, 13C NMR, ESI-MS and HRMS.

 


Keywords


houttuynoid b, intermediate, synthesis

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References


Chen SD, Gao H, Zhu QC, Wang YQ, Li T, Mu ZQ, et al. Houttuynoids A-E, anti-herpes simplex virus active flavonoids with novel skeletons from Houttuynia cordata. Organ Lett. 2012;14:1772–1775.

Kerl T, Berger F, Schmalz HG. Total synthesis of the antiviral natural product Houttuynoid B. Chemistry. 2016;22:2935–2938.

Brunskole M, Zorko K, Kerbler V, Martens S, Stojan J, Gobec S, et al. Trihydroxynaphthalene reductase of Curvularia lunata—a target for flavonoid action? Chem Biol Interact. 2009;178: 259–267.

Chiang LC, Chiang W, Liu MC, Lin CC. In vitro antiviral activities of Caesalpinia pulcherrima and its related flavonoids. J Antimicrob Chemother. 2003;52:194–198.

López-Posadas R, Ballester I, Abadía-Molina AC, Suárez MD, Zarzuelo A, Martínez-Augustin O, et al. Effect of flavonoids on rat splenocytes, a structure-activity relationship study. Biochem Pharmacol. 2008;76:495–506.

Vasquez-Martinez Y, Ohri RV, Kenyon V, Holman TR, Sepúlveda- Boza S. Structure-activity relationship studies of flavonoids as potent inhibitors of human platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2[J]. Bioorgan Med Chem. 2007;15:7408–7425.


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