Comparative routes to 7-carboxymethyl-pterin: A useful medicinal chemistry building block

Abstract

Pterins, such as folate and biopterin, and their derivatives hold significant importance given their biological relevance, as well as the numerous pterin-based inhibitors developed for targeting various biological targets. For this reason, pterins can be viewed as a privileged scaffold, as the discovery of new pterin analogs gives rise to a vast array of potential drug candidates. 7-carboxymethyl-pterin (7-CMP) represents a useful scaffold for the rapid generation of structurally diverse pterin amides and has been a key building block in medicinal chemistry. In an effort to facilitate rapid generation of this pterin scaffold, we have explored multiple routes towards 7-CMP to assess the most efficient method of generation. Methods were evaluated based on yield, regioselectivity, reaction time, and hazardous reaction conditions. This work can aide in the synthesis and discovery of new pterin-based drug candidates.

Keywords

• pterin
• regioselective synthesis
• medicinal scaffold