The quantitative pyrrole protection of l-phenylalanine/l-phenylalaninol in aqueous media and rationally updating the mechanisms of the Clauson-Kaas reaction through DFT study.

ABSTRACT: The classical Paal-Knorr reaction is a prominent tool that can be adopted under biocompatible conditions covering various γ-dicarbonyls for either chemical biology or drug discovery. Meanwhile, the relatively mild conditions for larger molecules within biological systems have not been employed to obtain N-substituted pyrrole derivatives from simpler chiral amino acids/alcohols. The Clauson-Kaas methodology of a standard two-phase acidic mixture buffered with acetate salts was generally required for the time-consuming catalytic condensation of 2,5-dimethoxytetrahydrofuran and fast removal of pyrrolyl products after formation to inhibit their racemization. To achieve a large amount of tethered pyrrole pendants based on l-phenylalanine to construct bioactive ureas as ASK1 and PI3K inhi

SUBMITTER: Qin Y 

PROVIDER: S-EPMC10711672 | biostudies-literature | 2023 Dec

REPOSITORIES: biostudies-literature