Synthesis, antimicrobial and cholinesterase enzymes inhibitory activities of indeno imidazoles and X-ray crystal structure of 3a,8a-dihydroxy-1,3- diphenyl-1,3,3a,8a-tetrahydro-indeno [1,2-d]imidazole-2,8-dione

摘要

Two indeno imidazoles have been synthesized by the reaction of ninhydrin with diphenylurea and diphenylthiourea. The structures have been determined by spectral analysis. The supramolecular behavior of 3a,8a-Dihydroxy- 1,3-diphenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole- 2,8-dione (1) was thoroughly analyzed and reported using X-ray single crystal technique and concepts. The presence of oxygen and nitrogen atoms led to very interesting supramolecularmotifs interactions such as nitrogen-oxygen, nitrogen- nitrogen, oxygen-oxygen, nitrogen-hydrogen, and oxygen- hydrogen. 3a,8a-dihydroxy-1,3- diphenyl-2-thioxo-2,3,3a,8atetrahydro- 1H-indeno[1,2-d]imidazol-8-one 2 showed good antibacterial activity against B. subtilis and P. aeruginosa, while 3a,8a-dihydroxy-1,3-diphenyl-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8- dione 1 only showed antibacterial activity against P. aeruginosa. Both of 1 and 2 were inactive against C. albicans. Derivative 2 demonstrated good cholinesterase enzyme activity unlike derivative 1 which has weak inhibitory activity against these enzymes. Furthermore, 2 was found to be a selective butyrylcholinesterase enzyme inhibitor that has potential use for prevention of further neurodegeneration as well for symptomatic treatment of Alzheimer patients.