Clozapine derived 2,3-dihydro-1H-1,4- and 1,5-benzodiazepines with D4 receptor selectivity: synthesis and biological testing

Hussenether, Thomas; Hübner, Harald; Gmeiner, Peter; Troschütz, Reinhard

doi:10.1016/j.bmc.2004.03.023

Cited by 28 publications

(22 citation statements)

References 33 publications

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“…1,5‐benzodiazepine derivatives constituted an important class of heterocyclic compounds possessing a wide spectrum of biological properties . The syntheses of new heterocyclic compounds are still in the continuous development because they are essentially links in the preparation of pharmaceuticals, as well as in the agrochemical industry .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure and Computational Investigation of New 4‐Phenyl‐decahydro‐1H‐1,5‐benzodiazepin‐2‐one as Potent Inhibitor of Mu‐opioid Receptor

Garadi¹,

Bakri

Lai

et al. 2020

ChemistrySelect

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A novel benzodiazepine derivative was prepared and characterized by elemental analysis, FT-IR, NMR ( 1 H and 13 C) and HR-MS methods. Its crystal structure was also investigated by single crystal X-ray diffraction. In the title compound, the fused 6-and 7-membered rings adopt chair and "twist boat" conformations, respectively. In the crystal, the molecules form inversion dimers through N-H⋅⋅⋅O hydrogen bonds and pack with no unusually short intermolecular contacts, which is in agreement with the results of the Hirshfeld surface analysis.The Hirshfeld surface analysis showed that the H⋅⋅⋅H contact was the most important interaction for the studied compound. Based on the DFTÀ B3LYP study, the studied compound owned a little different geometry in the gas phase concerning the solid phase. The molecular docking was performed between the title compound and a mu-opioid receptor. Molecular dynamics studies were also carried up to 50 ns to understand the stability for the title compound complex with the mu-opioid receptor.[a] Dr.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure and Computational Investigation of New 4‐Phenyl‐decahydro‐1H‐1,5‐benzodiazepin‐2‐one as Potent Inhibitor of Mu‐opioid Receptor

Garadi¹,

Bakri

Lai

et al. 2020

ChemistrySelect

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“…These compounds still are associated with some extrapyramidal side effects 3 . Literature reports that the compounds synthesized by removal of one of the benzene ring of clozapine were having same affinity on dopaminergic receptors to that of clozapine with minimization of its extrapyramidal side effects 4 . Clozapine, olanzapine, seroquel and other atypical antipsychotics have greater affinity for serotonin receptor than dopamine receptors 5,6 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Thienopyrimidines and their Antipsychotic Activity

Sharma¹,

Yerande²,

Chavan³

et al. 2009

Journal of Chemistry

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A series of thienopyrimidines and related heterocycles were synthesized by refluxing related imidoyl chloride with primary and secondary amines under microwave irradiation and classical heating. The imidoyl chlorides were synthesized from corresponding cyclic imides with phosphorus oxychlorides under microwave irradiation and classical heating. The structures of the compounds were confirmed by FT-IR, NMR. The synthesized compounds were screened for anti psychotic activity.

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“…These beneficial health properties have led to several investigations on their chemical structures and have initiated a number of synthetic efforts to access 1,5-benzodiazepine derivatives [15,[19][20][21][22][23][24][25][26][27][28]. In this work, we describe a new method for the synthesis of 3-hydroxy-1,5-benzodiazepin-2-ones based on the condensation of o-phenylenediamines with a cis and trans ethyl 3-phenylglycidate.…”

Section: Introductionmentioning

confidence: 99%

A Convenient Method for the Synthesis of 1,5-benzodiazepin-2-one

Rida¹,

Meslouhi²,

Ahabchane³

et al. 2008

TOOCJ

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New 3-hydroxy-1,5-benzodiazepin-2-ones were synthesized through condensation between ophenylenediamines with glycidic ester. Alkylation and oxidation of some of the obtained compounds were also explored in different conditions yielding various oxidized and alkylated benzodiazepines. The structural elucidation of the synthesized compounds was achieved by MS, NMR spectroscopy and also through X-ray diffraction analysis. The glycidic ester was thus shown to be an interesting synthon in the synthesis of new 1,5-benzodiazepines used in alkylation and oxidation reactions.

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Clozapine derived 2,3-dihydro-1H-1,4- and 1,5-benzodiazepines with D4 receptor selectivity: synthesis and biological testing

Cited by 28 publications

References 33 publications

Synthesis, Crystal Structure and Computational Investigation of New 4‐Phenyl‐decahydro‐1H‐1,5‐benzodiazepin‐2‐one as Potent Inhibitor of Mu‐opioid Receptor

Synthesis, Crystal Structure and Computational Investigation of New 4‐Phenyl‐decahydro‐1H‐1,5‐benzodiazepin‐2‐one as Potent Inhibitor of Mu‐opioid Receptor

Synthesis of Thienopyrimidines and their Antipsychotic Activity

A Convenient Method for the Synthesis of 1,5-benzodiazepin-2-one

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