A Review of Solid-Phase Organic Synthesis on SynPhase™ Lanterns and SynPhase™ Crowns

Abstract

This chapter reviews the solid-phase organic synthesis of various heterocycles on SynPhase Lanterns and SynPhase Crowns. Some of these heterocycles include benzodiazepines, purines, quinazolines, oxazoles, carbohydrates, and cyclic peptides. The solid-phase synthesis is a well-established tool in the pharmaceutical industry for the generation of large sets of small molecule compounds for lead finding and optimization. Mimotopes has been involved in the development, use, and commercialization of radiation-grafted polymer surfaces for multiple parallel syntheses. The graft polymer devices manufactured and sold by Mimotopes (SynPhase Crowns, SynPhase Lanterns) are the only current commercial products of this type. Benzodiazepines were the first class of heterocyclic compounds to be synthesized on the SynPhase surface. These compounds were prepared on the Mimotopes pins that were grafted with polyacrylic acid. In the case of quinazolines, polystyrene grafted SynPhase Lanterns were used to synthesize a diverse quinazoline-2 thioxo-4 one library. Lanterns functionalized with long-chain, HMP (hydroxymethylphenoxyvaleric amide) linker were coupled with nitrophenols by the action of DIC/HOAt/DMAP to give nitrobenzenes.