Synthesis and pharmacological evaluation of 11-(1,6-dimethyl-1,2,3,6-tetrahydropyridin-4-yl)-5H-dibenzo[b,e][1,4]diazepines with clozapine-like receptor occupancy at dopamine D1/D2 receptor

Bioorganic & Medicinal Chemistry Letters
2020.0

Abstract

Clozapine-like compound without agranulocytosis risk is need to cure the treatment resistant schizophrenia (TRS). We discovered (S)-3 as Clozapine-like dopamine D/D receptor selectivity and improved reactive metabolites formation profile by the modification of piperazine moiety in Clozapine. The optimization of (S)-3 gave compound 5 to be best compound (approximately 10-fold stronger affinity for D/D receptor and similar D/D selectivity ratio with Clozapine). Clozapine-like D/D receptor occupancy profile was proved by in vivo evaluation. In addition, the reactive metabolites derived agranulocytosis risk of compound 5 was considered to be lower than Clozapine. The pharmacology detail of compound 5 is being investigated to develop it for TRS treatment.

Knowledge Graph

Similar Paper

Synthesis and pharmacological evaluation of 11-(1,6-dimethyl-1,2,3,6-tetrahydropyridin-4-yl)-5H-dibenzo[b,e][1,4]diazepines with clozapine-like receptor occupancy at dopamine D1/D2 receptor
Bioorganic & Medicinal Chemistry Letters 2020.0
Identification of 2-fluoro-8-methyl-11-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5H-dibenzo[b,e][1,4]diazepine with clozapine-like mixed activities at muscarinic acetylcholine, dopamine, and serotonin receptors
Bioorganic & Medicinal Chemistry Letters 2021.0
Synthesis and biological evaluation of some 2-amino-4-aryl-3H-1,5-benzodiazepine analogs of clozapine
Journal of Medicinal Chemistry 1978.0
Synthesis and Pharmacological Evaluation of 1-[(1,2-Diphenyl-1H-4-imidazolyl)methyl]-4-phenylpiperazines with Clozapine-Like Mixed Activities at Dopamine D<sub>2</sub>, Serotonin, and GABA<sub>A</sub>Receptors
Journal of Medicinal Chemistry 2002.0
Synthesis and biological investigation of triazolopyridinone derivatives as potential multireceptor atypical antipsychotics
Bioorganic &amp; Medicinal Chemistry Letters 2020.0
Novel D2/5-HT receptor modulators related to cariprazine with potential implication to schizophrenia treatment
European Journal of Medicinal Chemistry 2022.0
Pyridobenzoxazepine and Pyridobenzothiazepine Derivatives as Potential Central Nervous System Agents: Synthesis and Neurochemical Study
Journal of Medicinal Chemistry 1994.0
Synthesis and Biological Investigation of Coumarin Piperazine (Piperidine) Derivatives as Potential Multireceptor Atypical Antipsychotics
Journal of Medicinal Chemistry 2013.0
Pharmacological evaluation of a diarylmethylene-piperidine derivative: a new potent atypical antipsychotic?
Bioorganic &amp; Medicinal Chemistry Letters 2001.0
Synthesis and evaluation of novel alkylpiperazines as potential dopamine antagonists
Journal of Medicinal Chemistry 1981.0