Intramolecular Aryne-Furan Cycloadditions for the Synthesis of Anticancer Naphthalimides

J Org Chem. 2018 Apr 20;83(8):4871-4881. doi: 10.1021/acs.joc.8b00531. Epub 2018 Apr 4.

Abstract

An intramolecular aryne Diels-Alder reaction with a furan moiety was applied to the synthesis of dihydrobenzo[ de]isochromenes as intermediates toward naphthalimides. After oxidation, this method offers an efficient approach for the synthesis of substituted naphthalimides, which showed potent cytotoxic activity against HT-29 human cancer cell line.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry*
  • Benzene Derivatives / chemistry*
  • Cycloaddition Reaction
  • Furans / chemistry*
  • Naphthalimides / chemical synthesis*
  • Naphthalimides / chemistry*

Substances

  • Antineoplastic Agents
  • Benzene Derivatives
  • Furans
  • Naphthalimides