Dihydro‐1,4‐Benzodiazepinones and Thiones

Walser, A.; Fryer, R. Ian

doi:10.1002/9780470187371.ch8

Cited by 8 publications

(7 citation statements)

References 195 publications

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“… a K i values are the mean ± SEM of three independent determinations. b GABA ratio = ( K i without GABA)/( K i with 50 μM GABA). c See ref . d Compounds 5g , h are referred to in the introduction as 4a , b , respectively (see ref ). …”

Section: Resultsmentioning

confidence: 99%

“…The title compound was resynthesized starting from 8b and following the above-cited procedure (yield 50%). Colorless crystals were obtained from cyclohexane–chloroform, mp 176–177 °C.…”

Section: Methodsmentioning

confidence: 99%

“…The synthesis of diazepinone derivatives 8aÀd,f,j-o and 10 was carried out starting from the suitable 2-aminobenzophenones following well-known procedures. 37,39,40 General Procedure for the Synthesis of Carboxamides 5qÀs. A solution of acid 16 (0.49 mmol) in CHCl 3 (3.0 mL) and TEA (0.070 mL, 0.95 mmol) was cooled at 15 °C and treated with of isobutyl chloroformate (0.51 mmol) while sirring at 15 °C for 1 h. The reaction mixture was treated with a suitable amine (0.50 mmol) (for 5q, gaseous NH 3 was bubbled into the reaction mixture until an insoluble residue appeared), stirred at the same temperature for 30 min, poured into iceÀwater, and then extracted with CH 2 Cl 2 .…”

Section: Ethyl 6-(4-chlorophenylmentioning

confidence: 99%

“…The synthetic route used to prepare benzodiazepinones 8a – d , f , j – n starting from the suitable 2-aminobenzophenones involved the sequential treatment with bromoacetyl bromide in dichloromethane to give the corresponding bromoacetamides and then with ammonia in ethanol at reflux or the reaction with glycine ethyl ester in pyridine at reflux. , On the other hand, racemic 3-substituted 1,4-benzodiazepinones 8e , i and 9 were prepared by condensation of the suitable benzophenone derivative ( 11e , i ) with alanine ethyl ester or aspartic acid dimethyl ester hydrochloride in pyridine (Scheme ).…”

Section: Chemistrymentioning

confidence: 99%

See 3 more Smart Citations

New Insight into the Central Benzodiazepine Receptor–Ligand Interactions: Design, Synthesis, Biological Evaluation, and Molecular Modeling of 3-Substituted 6-Phenyl-4H-imidazo[1,5-a][1,4]benzodiazepines and Related Compounds

et al. 2011

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3-Substituted 6-phenyl-4H-imidazo[1,5-a][1,4]benzodiazepines and related compounds were synthesized as central benzodiazepine receptor (CBR) ligands. Most of the compounds showed high affinity for bovine and human CBR, their K(i) values spanning from the low nanomolar to the submicromolar range. In particular, imidazoester 5f was able to promote a massive flow of (36)Cl(-) in rat cerebrocortical synaptoneurosomes overlapping its efficacy profile with that of a typical full agonist. Compound 5f was then examined in mice for its pharmacological effects where it proved to be a safe anxiolytic agent devoid of the unpleasant myorelaxant and amnesic effects of the classical 1,4-benzodiazepines. Moreover, the selectivity of some selected compounds has been assessed in recombinant α(1)β(2)γ(2)L, α(2)β(1)γ(2)L, and α(5)β(2)γ(2)L human GABA(A) receptors. Finally, some compounds were submitted to molecular docking calculations along with molecular dynamics simulations in the Cromer's GABA(A) homology model.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Ethyl 6-(4-chlorophenylmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

See 2 more Smart Citations

New Insight into the Central Benzodiazepine Receptor–Ligand Interactions: Design, Synthesis, Biological Evaluation, and Molecular Modeling of 3-Substituted 6-Phenyl-4H-imidazo[1,5-a][1,4]benzodiazepines and Related Compounds

et al. 2011

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“…Benzodiazepines play an important role in medicinal chemistry due to a wide range of pharmaceutical applications [1][2][3][4][5][6][7]. Much of the biological activities are concerning the action in the central nervous system.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Benzodiazepines Synthesis

2020

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This review is focused on palladium-catalyzed reactions as efficient strategies aimed at the synthesis of different classes of benzodiazepines. Several reaction typologies are reported including hydroamination, amination, C–H arylation, N-arylation, and the Buchwald–Hartwig reaction, depending on the different substrates identified as halogenated starting materials (activated substrates) or unactivated unsaturated systems, which then exploit Pd(0)- or Pd(II)-catalytic species. In particular, the use of the domino reactions, as intra- or intermolecular processes, are reported as an efficient and eco-compatible tool to obtain differently functionalized benzodiazepines. Different domino reaction typologies are the carboamination, aminoarylation, aminoacethoxylation, aminohalogenation, and aminoazidation.

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