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

• Dehydrophenylalalnylglycinyl/cysteinyl dicyclohexylurea analogs (3a–3o) were synthesized.
• Compounds 3a and 3h exhibited moderate anti-inflammatory and analgesic activities.
• Compound 3j displayed potent antimicrobial and antioxidant activities.
• Docking studies on compound 3j with penicillin binding protein and protease supported the results.

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.

Among the synthesized N-dehydrodipeptidyl-N,N′-dicyclohexylurea analogs (3a–3o), 3j exhibited potent antioxidant and antimicrobial activities. Docking studies on 3j and amoxicillin with penicillin binding protein showed similar interactions.Figure optionsDownload as PowerPoint slide