Synthesis and biological evaluation of N-dehydrodipeptidyl-N,N'-dicyclohexylurea analogs

• Published in: European journal of medicinal chemistry Vol. 78; pp. 72 - 85
• Main Authors: Haseena banu, B, Prasad, K V S R G, Bharathi, K
• Format: Journal Article
• Language: English
• Published: France 06-05-2014
• Subjects: Acetic Acid; Analgesics - chemical synthesis; Analgesics - chemistry; Analgesics - pharmacology; Animals; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis; Anti-Inflammatory Agents, Non-Steroidal - chemistry; Anti-Inflammatory Agents, Non-Steroidal - pharmacology; Antifungal Agents - chemical synthesis; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Bacteria - drug effects; Carrageenan; Dose-Response Relationship, Drug; Edema - chemically induced; Edema - drug therapy; Fungi - drug effects; Mice; Microbial Sensitivity Tests; Models, Molecular; Molecular Structure; Pain - chemically induced; Pain - drug therapy; Rats; Structure-Activity Relationship; Urea - analogs & derivatives; Urea - chemical synthesis; Urea - pharmacology; Antimicrobial; Dehydrophenylalanyl; Antioxidant; Dicyclohexylurea; Protease; Penicillin binding protein
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2014.03.037

Some N-[(N-benzoyldehydrophenylalalnyl)glycinyl/cysteinyl]-N,N'-dicyclohexylurea analogs (3a-3o) were synthesized by conjugating different substituted N-benzoyldehydrophenylalanyl glycines/cysteines (differing substitutions on benzylidene ring) and dicyclohexyl carbodiimide (DCC) using base as a catalyst. The synthesized compounds were characterized and evaluated for biological activities. Compounds 3a and 3h with unsubstituted dehydrophenylalanyl glycinyl/cysteinyl moiety exhibited moderate anti-inflammatory and analgesic activities. Compound 3j bearing 4-hydroxy substitution on benzylidene ring of dehydrophenylalanyl cysteinyl moiety displayed potent antimicrobial and antioxidant activities. The results obtained from docking studies on compound 3j with penicillin binding protein and protease supported the results.