An Improved Synthesis of 2-Methyl-4-(2'-carboxyethyl)pyrrole. Potential Inhibitors of Porphobilinogen Deaminase

Abstract

Improved syntheses of 2-methyl-4-(2'-carboxyethyl)pyrrole (10) (49% o v e r a l l y i e l d ) and of several 0-and S-containing 8 -( 5 -r i n g heteroc y c l i c ) -s u b s t i t u t e d propionic acids are described.Some of these compounds have been found t o be i n h i b i t o r s o f porphobilinogen deaminase.I n connection w i t h a study of porphobilinogen (PEG) deaminase, an enzyme o f t h e heme b i o s y n t h e t i c pathway, we sought t o examine the p o t e n t i a l of simple h e t e r o c y c l i c c a r b o x y l i c a c i d