Synthesis and antitumor, antityrosinase, and antiplatelet aggregation activities of xanthone

doi:10.5246/jcps.2019.04.025

Abstract

Abstract:

In the present study, five fluorine substituted and three chlorine substituted 1,3-dihydroxyxanthones were synthesized in one step.The yields ranged from 48% to 72%. Among them, compounds 12 and 15–18 were reported for the first time. The antitumor, antityrosinase and antiplatelet aggregation activities of all or part of compounds 1–19 were evaluated. Compounds 1, 2, 4, 6–7, 10–15 and 19 exhibited enhanced cytotoxicity against certain cancer cells. Compound 10,containing 2,4-difluorophenyl at the C7 position, particularly exhibited superior antitumor activity. The inhibition rate of compound 18 against tyrosinase was approximately 22%. Compounds 1–3, 6, 9, 12 and 18, 19 exhibited obvious inhibitory platelet aggregation induced by ADP in rats. Moreover, the effects of compounds 2 and 3 were more pronounced. These results demonstrated that compounds 1–4, 6–7, 9–15 and 19 were promising leads for further structural modification.

Key words: Xanthone, Synthesis, Antitumor, Antityrosinase, Antiplatelet aggregation

CLC Number:

R916

Supporting:

The ¹H NMR spectrum of 5-fluoro-1,3-dihydroxy-9H-xanthen-9-one (11) (DMSO-d₆, 500 MHz)

The ¹³C NMR spectrum of 5-fluoro-1,3-dihydroxy-9H-xanthen-9-one (11) (DMSO-d₆, 125 MHz)

The ¹H NMR spectrum of 6-fluoro-1,3-dihydroxy-9H-xanthen-9-one (12) (DMSO-d₆, 500 MHz)

The ¹³C NMR spectrum of 6-fluoro-1,3-dihydroxy-9H-xanthen-9-one (12) (DMSO-d₆, 125 MHz)

The ¹H NMR spectrum of 7-fluoro-1,3-dihydroxy-9H-xanthen-9-one (13) (DMSO-d₆, 500 MHz)

The ¹³C NMR spectrum of 7-fluoro-1,3-dihydroxy-9H-xanthen-9-one (13) (DMSO-d₆, 125 MHz)

The ¹H NMR spectrum of 8-fluoro-1,3-dihydroxy-9H-xanthen-9-one (14) (DMSO-d₆, 500 MHz)

The ¹³C NMR spectrum of 8-fluoro-1,3-dihydroxy-9H-xanthen-9-one (14) (DMSO-d₆, 125 MHz)

The ¹H NMR spectrum of 1,2-difluoro-6,8-dihydroxy-9H-xanthen-9-one (15) (DMSO-d₆, 500 MHz)

The ¹³C NMR spectrum of 1,2-difluoro-6,8-dihydroxy-9H-xanthen-9-one (15) (DMSO-d₆, 125 MHz)

The ¹H NMR spectrum of 5-chloro-1,3-dihydroxy-9H-xanthen-9-one (16) (DMSO-d₆, 500 MHz)

The ¹³C NMR spectrum of 5-chloro-1,3-dihydroxy-9H-xanthen-9-one (16) (DMSO-d₆, 125 MHz)

The ¹H NMR spectrum of 5,7-dichloro-1,3-dihydroxy-9H-xanthen-9-one (17) (DMSO-d₆, 500 MHz)

The ¹³C NMR spectrum of 5,7-dichloro-1,3-dihydroxy-9H-xanthen-9-one (17) (DMSO-d₆, 125 MHz)

The ¹H NMR spectrum of 1,2,4-trichloro-6,8-dihydroxy-9H-xanthen-9-one (18) (DMSO-d₆, 500 MHz)

The ¹³C NMR spectrum of 1,2,4-trichloro-6,8-dihydroxy-9H-xanthen-9-one (18) (DMSO-d₆, 125 MHz)

Beidou Zhou, Xin Wang, Zhimin Weng, Baocheng Huang, Zetong Ma, Bo Yu, Liqin Ruan, Dongbao Hu. Synthesis and antitumor, antityrosinase, and antiplatelet aggregation activities of xanthone[J]. Journal of Chinese Pharmaceutical Sciences, 2019, 28(4): 247-256.

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