610-38-8Relevant articles and documents
Synthesis and dual D2 and 5-HT1A receptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones
Ullah, Nisar
, p. 281 - 291 (2014/04/03)
A series of new 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)- ones have been synthesized and evaluated for dual D2 and 5-HT1A receptor binding affinities. The synthesized ligands are structurally related to bifeprunox, a potential atypical antipsychotic, having potent D2 receptor antagonist and 5-HT1A receptor agonist properties. The Suzuki-Miyaura reaction of cyclic vinyl boronate with appropriate aryl halide yielded arylpiperidine, which was eventually transformed to piperidinyl-1H-benzo[d]imidazol-2(3H)-one. The reductive amination of the latter with appropriate biarylaldehdyes rendered the synthesis of 5-piperidinyl-1H-benzo[d]imidazol-2(3H)-ones. Likewise, the Buchwald-Hartwig coupling reactions of 1-boc-piperazine with appropriate aryl halide and subsequent removal of the boc group rendered arylpiperazine. The reductive amination of the latter with appropriate biarylaldehdyes accomplished the synthesis of 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones. The structure-activity relationship studies showed that cyclopentenylpyridine and cyclopentenylbenzyl groups contribute significantly to the dual D2 and 5-HT1A receptor binding affinities of these compounds.
Competitive Cyclisations of Singlet and Triplet Nitrenes. Part 8. The 1-(2-Nitrenophenyl)pyrazoles and Related Systems
Lindley, John M.,McRobbie, Ian M.,Meth-Cohn, Otto,Suschitzky, Hans
, p. 982 - 994 (2007/10/02)
The title nitrenes, derived by nitro-group deoxygenation with triethyl phosphite or by thermolysis or photolysis of the corresponding azide, have been studied.The effect of substituents (Cl, Br, OMe, NMe2, Me, CF3, and NO2) both meta and para to the nitrene has been examined as a determinant of the preferred mode of cyclisation to either a pyrazolobenzotriazole or a pyrazoloquinoxaline.Similarly, the role of solvents, sensitisers, and quenchers has been studied.Routes to the isomeric 1- and 2-(2-nitrophenyl)-4,5,6,7-tetrahydroindazoles have been defined and the literature corrected by studing the nitrene-mediated cyclisation of these products.The chemistry of the analogous 1-(2-carbenophenyl)- and the 1-(2-nitrenosulphonylphenyl)-3,5-dimethylpyrazoles has also been examined, the former giving 2-(3,5-dimethylpyrazol-1-yl)-benzaldazine and -benzyl alcohol while the latter gave products of intramolecular nitrene attack (a pyrazolobenzothiatriazine) and intermolecular reaction.Rationalisations for all the reaction pathways have been advanced.