Synthesis, characterization and biological screening of some new aryloxyacetic acid analogs

Depertment of Pharmaceutical Chemistry, Rajiv Academy for Pharmacy, Mathura-281 001,

Uttar Pradesh, India

E-mail : rajivdahiya04@yahoo.co.in; rajivdahiya77@rediffmail.com

Manuscript received 26 November 2007, revised 1 April 2008, accepted 6 May 2008

A novel series of 2-(4-bromo-2-formyl-phenoxy)acetyl amino acid and peptide analogs was synthesized by the coupling of 2-(4-bromo-2-formyl-phenoxy)acetic acid with different amino acid methyl ester hydrochlorides, dipeptide and tripeptide methyl esters using dicyclohexylcarbodiimide as the coupling agent and N-methylmorpholine as the base. Structures of all the newly synthesized compounds were elucidated on basis of IR, NMR and MS spectral data as well as elemental analysis. On pharmacological screening, some peptide derivatives were found to exhibit potent bioactivity against gram-negative bacterium Pseudomonas aeruginosa, pathogenic fungus Candida albicans and earthworms Megascoplex konkanensis, Pontoscotex corethruses and Eudrilus sp. Dermatophytes were found to be moderately sensitive towards the newly synthesized analogs. Hydrolyzed peptide derivatives displayed better antimicrobial activity in comparison to corresponding esters.