Studies on Nitrofuran and Related Compounds for Medicinal Purpose. VIII

Syntheses of 2-Alkylthiopyrimidine Derivatives with Nitrofuran Nucleus and their Structure-Activity Relationship

Abstract

2-Alkylthio-4-(5-nitro-2-furylalkenyl)pyrimidines (VI) shown in Table I were readily obtained by an acid-catalyzed condensation of 2-alkylthio-4-methylpyrimidines (IV) with 5-nitro-2-furyl-aldehydes (V) in a fairly good yield. VI was highly susceptible to photodecomposition and some of them failed to show normal ultraviolet absorption spectra. Antibacterial activity of VI against Escherichia coli O-18 and Staphylococcus aureus 209P was tested in three kinds of bouillon medium, and the result (Table III) showed that 2-methylthio-4-[3-methyl-4-(5-nitro-2-furyl)-1, 3-butadienyl]pyrimidine had the highest activity among them.