N‐Formamido‐Containing Mono‐ and Diheterocyclic Pyrrole‐and Imidazole‐2‐carboxylic Acids as Building Blocks for Polyamide Synthesis

Abstract

Four N‐formamido‐containing mono‐and diheterocyclic pyrrole‐ and imidazole‐2‐containing acids 1–4 were synthesized as intermediates for the preparation of polyamide molecules. The N‐formamido‐moiety forces the compounds to bind strongly as a stacked dimer, and in a staggered fashion, at specific sequences in the minor‐groove of DNA. The acid moiety at the C‐terminus of compounds enables these molecules to be coupled to amine‐containing intermediates to form the amide linkages of the target polyamide. This convergent approach increases the synthetic diversity in polyamide chemistry by enabling one acid to be used with a variety of different C‐terminus‐functionalized intermediates.

Keywords:

• acid
• distamycin
• DNA
• formamido
• polyamide

Acknowledgment

The authors thank the National Science Foundation for support of this project.