N-Glucopyranosyl-5-aralkylidenerhodanines: synthesis and antibacterial and antiviral activities.
A series N-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-5-aralkylidenerhodanines was synthesized, and the acetyl groups were removed to give N-beta-D-glucopyranosyl-5-aralkylidenerhodanies  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-beta-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.
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000998:Antiviral Agents / Q000138:chemical synthesis*; D001419:Bacteria / Q000187:drug effects; D001786:Blood Glucose / Q000378:metabolism; D002478:Cells, Cultured; D006224:Cricetinae; D012313:RNA / Q000096:biosynthesis; D012367:RNA, Viral / Q000096:biosynthesis; D012236:Rhodanine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D013844:Thiazoles / Q000138:chemical synthesis*
D000900:Anti-Bacterial Agents; D000998:Antiviral Agents; D001786:Blood Glucose; D012367:RNA, Viral; D013844:Thiazoles; D012313:RNA; D012236:Rhodanine