Synthesis of novel 2-mercapto benzothiazole and 1,2,3-triazole based bis-heterocycles: Their anti-inflammatory and anti-nociceptive activities

A focused library of novel bis-heterocycles encompassing 2-mercapto benzothiazole and 1,2,3-triazoles were synthesized using click chemistry approach. The synthesized compounds have been tested for their anti-inflammatory activity by using biochemical cyclooxygenase (COX) activity assays and carrageenan-induced hind paw edema. Among the tested compounds, compound 4d demonstrated a potent selective COX-2 inhibition with COX-2/COX-1 ratio of 0.44. Results from carrageenan-induced hind paw edema showed that compounds 4a, 4d, 4e and 4f posses significant anti-inflammatory activity as compared to the standard drug Ibuprofen. The compounds showing significant activity were further subjected to anti-nociceptive activity by writhing test. These four compounds have shown comparable activity with the standard Ibuprofen. Further ulcerogenic studies shows that none of these compounds causing gastric ulceration.

Novel bis-heterocycles encompassing 2-mercapto benzothiazole and 1,2,3-triazoles demonstrated a potent selective COX-2 inhibition and significant anti-inflammatory activity as compared to the standard drug Ibuprofen without causing any ulceration.Figure optionsDownload as PowerPoint slideHighlights
► New bis-heterocycles bearing 2-mercapto benzothiazole and triazoles were synthesized.
► Some of the compounds demonstrated a potent selective COX-2 inhibition.
► Molecular docking study also confirms strong binding potential towards COX-2.
► Significant anti-inflammatory activity in vivo was observed as compared to Ibuprofen.
► Compounds 4d and 4e are showing better analgesic activity compared to Ibuprofen.