Synthesis of a 7-aminomethylindole and related bis-indole derivatives

Hakan Kandemir,Ibrahim F Sengul,David Stc Black,Naresh Kumar

doi:10.3998/ark.5550190.p009.587

Abstract

Synthesis of a 7-aminomethylindole and related bis-indole derivatives

Highlights

Brassinin 1 and cyclobrassinin 2, are representative members of the phytoalexin family that have been isolated from cabbage and exhibit antitumor activity
Aminomethylindole based bis-indoles have been isolated from natural sources and demonstrate potential as biologically active compounds and useful synthetic targets
The amide linked bis-indoles were obtained upon reaction of 7-aminomethylindole 6 with acyl chlorides, while an imine linked compound 12 was produced upon reaction with 7-formylindole 11

Summary

Introduction

The aminomethyl moiety is found in many indole alkaloids which possess biological activity.1 For example, brassinin 1 and cyclobrassinin 2, are representative members of the phytoalexin family that have been isolated from cabbage and exhibit antitumor activity.2 During the last two decades, approximately thirty phytoalexins have been isolated from cruciferous plants. The first target 7,7′-bis-indole carboxamide 8 was prepared in 83% yield by the reaction of equimolar amounts of 7-aminomethyindole 6 and 7-trichloroacetylindole 78 in hot acetonitrile (Scheme 2). In the 1H NMR spectrum of compound 10, for example, the amide NH appeared as a triplet at 8.27 ppm, while the indole NH resonance was observed at 10.91 ppm.

Results

Conclusion