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

Abstract

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 supramolecular motifs interactions such as nitrogen-oxygen, nitrogennitrogen, oxygen-oxygen, nitrogen-hydrogen, and oxygenhydrogen. 3a,8a-dihydroxy-1,3-diphenyl-2-thioxo-2,3,3a,8a-tetrahydro-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.

Ninhydrin in synthesis of heterocyclic compounds

“…Subsequently, the same group synthesized two indeno imidazoles 209 from the reaction of ninhydrin with diphenylurea or diphenylthiourea 208 and examined their antimicrobial activities, which showed good antibacterial activity against B. subtilis and P. aeruginosa (Scheme 61). 274 However, the authors did not determine or comment on the stereochemistry of the compounds.…”

Ternary Inclusion System of Chair Conformation of 4,6,10,12,16,18,22,24-Octahydroxy-2,8,14,20-tetraphenyl-resorcin[4]arene: Selective Green Synthesis, Supramolecular Behavior, and Biological Activity

“…Our research group has been interested in designing and preparing different types of host molecules, and investigating their ability to form host-guest complexes with different guests' functionalities [19][20][21][22][23][24][25][26][27][28][29][30][31][32]. Herein, we describe the selective synthesis, structural conformation, supramolecularity, and bioactivity of the chair conformation of 4,6,10, 12,16,18,22,24-octahydroxy-2,8,14,20-tetraphenyl-resorcin[4]arene host 3 (Scheme 1) and its DMSO-H 2 O ternary inclusion system, as part of an ongoing project aiming to design, synthesize, and investigate new calix [4] arenes compounds [33,34].…”

A facile approach for the synthesis of indenoimidazole derivatives and their supramolecular study

“…8 Our previous studies, reported synthesis, crystal structures, supramolecularity of several indenoimidazoles with antimicrobial and cholinesterase enzymes inhibitory activities. 9,20,22 The title adducts have been synthesized in minimum time (15 min) with maximum yields (95%). Nowadays, supramolecular chemists are interested in design, synthesis, and characterization of supramolecular assemblies, which have the ability to work as functional materials.…”