Design, Synthesis and Analgesic Activity of 3-Chlorobenzoyl-N-(2-amino-4-chlorophenyl)anthranilic acid

Abstract

Anthranilic acid derivatives such as a mefenamic acid are well known as an analgesic drug. modification of anthranilic acid derivate was designed to get better analgesic activity. Docking studies were performed using Molegro Virtual Docker 5.0 software with the protein target cyclooxygenase-2 receptor (PDB ID: 5IKR). The synthesis was carried out by modification Scotten Baumann reaction via nucleophilic reaction of N-(2-amino-4-chlorophenyl)anthranilic acid and 3-chlorobenzoyl chloride. Synthesized compound was characterized by IR, 1H-NMR, 13C-NMR, Mass spectrometry. Biological activity for analgesic of the proposed compound by writhing test method on mice (Mus musculus). The result from docking studies revealed that rerank score of 3-chlorobenzoyl-N-(2-amino-4-chlorophenyl) anthranilic acid get lower than mefenamic acid which related its higher analgesic activity. 3-Chlorobenzoyl-N-(2-amino-4-chlorophenyl)anthranilic acid showed better pain inhibition activity compare mefenamic acid with ED50 = 30.443 mg/kgBW. This result gave a development of anthranilic acid derivate to be potential analgesic drug candidate.