Diastereoselective synthesis of substituted hexahydrobenzo[de]isochromanes and evaluation of their antileishmanial activity

Org Biomol Chem. 2016 Jan 21;14(3):970-9. doi: 10.1039/c5ob02038g. Epub 2015 Dec 2.

Abstract

Hexahydrobenzo[de]isochromanes and hexahydropyrano[3,4,5-ij]isoquinolines can be efficiently synthesized via Friedel Crafts and oxa Pictet-Spengler reaction of acrylyl enol ethers mediated by triflic acid in good yields. The reaction is highly stereoselective. Two of the hexahydrobenzo[de]isochromanes are found to have moderate antileishmanial activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemical synthesis
  • Acetates / chemistry
  • Acetates / pharmacology*
  • Antiprotozoal Agents / chemical synthesis*
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / pharmacology*
  • Benzopyrans / chemical synthesis
  • Benzopyrans / chemistry
  • Benzopyrans / pharmacology*
  • Dose-Response Relationship, Drug
  • Leishmania donovani / drug effects*
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Acetates
  • Antiprotozoal Agents
  • Benzopyrans
  • ethyl 2-(3-(4-methoxyphenyl)-3a,6,6-trimethyl-1,3,3a,4,5,6-hexahydro-benzo(de)isochroman-1-yl)acetate
  • ethyl 2-(8-bromo-6,6-dimethyl-1,3,3a,4,5,6-hexahydrobenzo(de)isochroman-1-yl)acetate