Lophine (2,4,5-triphenyl-1H-imidazole)

Abstract

The title compound, C21H16N2, has been known since 1877. Although the crystal structure of 36 derivatives of lophine are known, the structure of parent compound has remained unknown until now. The three phenyl rings bonded to the imidazole core are not coplanar with the latter, with dihedral angles of 21.4 (3), 24.7 (3), and 39.0 (3)°, respectively, between the phenyl ring planes in the 2-, 4- and 5-positions of the imidazole ring. The mol­ecules are packed in layers running perpendicular to the b axis. Although there are acceptor and donor atoms for hydrogen bonds, no such inter­actions are detected in the crystal in contrast to other lophine derivatives.

Synthesis of tacrine-lophine hybrids via one-pot four component reaction and biological evaluation as acetyl- and butyrylcholinesterase inhibitors

“…Also, hybrids with chloride substituent in the meta-position (entries 3 and 10) were inactive toward AChE. This result could be explained as a consequence of the fact that all phenyl rings bonded to the imidazole core are not coplanar and the dihedral angles between the phenyl ring planes can be increased with substituent groups in the meta-position [33]. So, it can be inferred that the loss of AChE activities with substituent at phenyl metasubstituted hybrids results from a smaller pep interaction of lophine framework with the active sites of the enzyme.…”

Synthesis, characterization, and crystal structure analysis of 2-(2-hydroxy-3-methoxyphenyl)-1-(4-chlorophenyl)-4,5-diphenyl-1h-imidazole

“…The molecular and packing diagrams were generated using the software MERCURY [17]. X-ray diffraction analysis revealed that the title compound is crystallized in the tetragonal crystal system with the space group P4 3 The bond lengths and bond angles are comparable with those reported earlier for lophine (2,4,5-triphenyl-1H-imidazole) [18]. The imidazole ring N1/C2/N3/C4/C5 is planar as confirmed by the torsion angles of its segments.…”

Synthesis and Structure of 1-Ethyl-2,4,5-triphenyl-1H-imidazole (Ethyl-Lophine)

“…Until now, crystal structures of more than 30 derivatives are known, and recently the crystal structure of the parent compound lophine has been reported [37]. The single-crystal Xray structure of 1-ethyl-2,4,5-triphenyl-1H-imidazole has now been established by X-ray diffraction analysis.…”