Total Synthesis and Antitumor Activity of Three 6-Geranylated Flavanones

doi:10.11944/j.issn.1000-0518.2017.10.160494

Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (10): 1140-1149.DOI: 10.11944/j.issn.1000-0518.2017.10.160494

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Total Synthesis and Antitumor Activity of Three 6-Geranylated Flavanones

MA Tao,YANG Jinhui(),NIU Mingjie,YE Ziping,LI Fanghui

College of Chemistry and Chemical Engineering,Ningxia University,Yinchuan 750021,China

Received:2016-12-05 Accepted:2017-02-12 Published:2017-09-29 Online:2017-09-29
Contact: YANG Jinhui
Supported by:
Supported by the National Natural Science Foundation of China(No.21362025)

Abstract

Abstract:

Three geranylated flavanones isolated from the bark of Paulownia tomentosa were synthesized from phloroacetophenone and substituted hydroxybenzaldehydes via substitution, protection of phenolic hydroxyl group, aldol condensation, cyclization and deprotection reactions. Their structures were confirmed by proton and carbon(¹H and ¹³C) nuclear magnetic resonance(NMR) and high resolution mass spectrometry(HRMS). The inhibition assay of these flavanones against A459 cell by methyl thiazolyl tetrazolium(MTT) protocol, indicates that compound 2 exihibits the highest activity with an half maximal inhibitory concentration(IC₅₀) value at 25.6 μmol/L. This study provides a suggestion for drug development based on geranylated flavanone scaffold.

Key words: Paulownia tomentosa, geranylated flavanones, flavanone, total synthesis, antitumor activity

MA Tao, YANG Jinhui, NIU Mingjie, YE Ziping, LI Fanghui. Total Synthesis and Antitumor Activity of Three 6-Geranylated Flavanones[J]. Chinese Journal of Applied Chemistry, 2017, 34(10): 1140-1149.

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Total Synthesis and Antitumor Activity of Three 6-Geranylated Flavanones

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