Medicinal Chemistry

Synthesis, of Novel Piperine Analogs of Dipeptidyl Boronic Acid as Antimicrobial and Anticancer Agents

Abstract

Durvasula V.R. Venugopal, Nagendra Sastry Yarla and Parimi Umadevi

In the present study three piperine analogs of dipeptidyl boronic acid (1 to 3) were synthesized and evaluated the antimicrobial and anticancer activities. Chemical structures of the synthesized compounds were characterized by 1H, 13C and mass spectral studies. All the compounds were screened for their antineoplastic activity on HeLa cervical, MCF-7 breast and MIA PaCa-2 pancreatic cancer cell lines and antimicrobial activity against seven bacterial and five fungal species. In vitro results showed that most of the compounds displayed moderate to good inhibitory activity on the tested cancer cell lines, among them compound 1 showed good anticancer activity where as Compound 3 was found to be potent antimicrobial agent against Asperigillus fumigates at a concentration of 62 μg/mL than other tested compounds and the parent molecule piperine. All the compounds were subjected to molecular docking studies on Leucyl-tRNA synthase as well as for 20S proteasome inhibition. In silico molecular docking results demonstrated that all compounds had low binding energy toward the active pocket and thus they may act as a good Leucyl-tRNA synthase inhibitor.