N glucopyranosyl 5 aralkylidenerhodanines: Synthesis and antibacterial and antiviral activities

Article abstract of DOI:10.1002/jps.2600661126

A series of N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-aralkylidenerhodanines was synthesized, and the acetyl groups were removed to give N-β-D-glucopyranosyl-5-aralkylidenerhodanines without cleavage of the rhodanine ring by means of acid hydrolysis. Alkaline hydrolysis with ammonia in methanol resulted in cleavage to N-glucosylthiourea, providing evidence for N-glycoside formation. A number of the rhodanine derivatives, especially those with nitro or chloro groups in the aromatic ring, showed antibacterial activity. N-β-D-Glucopyranosyl-5-(4-nitrobenzylidene)rhodanine showed antiviral activity by inhibition of viral RNA synthesis. Some effect on blood sugar levels also was observed with several rhodanines.