Synthesis and anti-inflammatory evaluation of methylene bridged benzofuranyl imidazo[2,1-b][1,3,4]thiadiazoles

A series of 6-substituted and 5,6-disubstituted 2-(6-methyl-benzofuran-3-ylmethyl)-imidazo[2,1-b][1,3,4]thiadiazoles have been synthesized. The new compounds have been tested for their in vivo analgesic, anti-inflammatory activities. Qualitative SAR studies indicate that the chloro substitution in the imidazole ring and introduction of formyl group at C-5 position of the imidazole ring increased the anti-inflammatory and analgesic activity. All the newly synthesized compounds have been characterized by spectral data and ORTEP diagram of one of the intermediates 6-(4-chlorophenyl)-2-(6-methyl-benzofuran-3-ylmethyl)-5-morpholin-4-ylmethyl imidazo[2,1-b][1,3,4]thiadiazole is reported herein.

Graphical abstractA variety of methylene bridged benzofuran-3-yl imidazothiadiazoles have been synthesized starting from 6-methyl benzofuran-3-acetic acid and thiosemicarbazide. The intermediate amino thiadiazole obtained has been reacted with phenacyl bromides to obtain the title skeleton. The reactivity of this system has been exploited to introduce various groups at C-5. The new compounds have been screened for their anti-inflammatory and analgesic activities. All the newly synthesized compounds have been characterized by spectral data and ORTEP diagram of one of the intermediates 6-(4-chlorophenyl)-2-(6-methyl-benzofuran-3-ylmethyl)-5-morpholin-4-ylmethyl imidazo[2,1-b][1,3,4]thiadiazole is reported herein. Figure optionsDownload full-size imageDownload as PowerPoint slide