A Simple and Efficient Method for The Synthesis of Vascular Disrupting Agent AVE-8063
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R914.5

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    Abstract:

    A new synthetic protocol leading to vascular disrupting agent (Z)-3′-amino-3,4,4′,5-tetramethoxylstilbene (AVE-8063) was successfully devised. Starting from 4-methoxyphenylacetic acid, (E)-2-(3-bromo-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl) acrylic acid (Ⅲ) could readily be obtained through bromination and Perkin condensation. Amination of (Ⅲ) afforded (E)-2-(3-animo-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)acrylic acid (Ⅳ), which was subsequently decarboxylated in Cu/1,10-Phen/PEG-400 system under microwave conditions for 6 min to give the target product (Ⅴ) with 60.1% total yield. The structure of the product was verified by IR, MS and 1H NMR.

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History
  • Received:December 13,2012
  • Revised:January 15,2013
  • Adopted:January 24,2013
  • Online: May 03,2013
  • Published: