3967-01-9

Usage

Uses

Used in Pharmaceutical Industry:
4-METHYL-1,3,4,5-TETRAHYDRO-2H-1,5-BENZODIAZEPIN-2-ONE is used as a sedative for inducing a calming and relaxing effect on the central nervous system, helping to alleviate anxiety and promote sleep.
Used in Medical Treatments:
4-METHYL-1,3,4,5-TETRAHYDRO-2H-1,5-BENZODIAZEPIN-2-ONE is used as an anxiolytic to treat conditions characterized by excessive anxiety, providing relief by reducing the symptoms associated with anxiety disorders.
Used in Sleep Aid Formulations:
4-METHYL-1,3,4,5-TETRAHYDRO-2H-1,5-BENZODIAZEPIN-2-ONE is used as a hypnotic agent to facilitate sleep onset and improve sleep quality in individuals experiencing insomnia or other sleep disturbances.

InChI:InChI=1/C10H12N2O/c1-7-6-10(13)12-9-5-3-2-4-8(9)11-7/h2-5,7,11H,6H2,1H3,(H,12,13)/t7-/m1/s1

Upstream product

• 6276-48-8 4-methyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one 
• 3724-65-0 2-butenoic acid 
• 95-54-5 1,2-diamino-benzene 
• 107-93-7 (E)-but-2-enoic acid 
• 55889-32-2 (E)-1-(1H-benzo[d][1,2,3]triazol-1-yl)but-2-en-1-one 
• 1493-27-2 ortho-nitrofluorobenzene 
• 1407835-16-8 ethyl 3-(2-nitrophenylamino)butanoate 
• 1407835-19-1 ethyl 3-(2-aminophenylamino)butanoate 
• 674-82-8 4-methyleneoxetan-2-one 

Downstream Products

• 78679-16-0 1,4,5-trimethyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one 
• 172686-19-0 4,5-dimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one 
• 40358-34-7 2-methyl-2,3,4,5-tetrahydro-1H-benzo[b] [1,4] diazepine 
• 74389-71-2 4-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione 
• 200264-16-0 5-Benzyl-4-methyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one 
• 144400-94-2 5-crotonoyl-4-methyl-1H-2,3,4,5-tetrahydro-1,5-benzodiazepin-2-one 
• 144400-95-3 5-cinnamoyl-4-methyl-1H-2,3,4,5-tetrahydro-1,5-benzodiazepin-2-one 
• 1380571-19-6 C₁₇H₁₉N₅O 
• 74389-73-4 1,5-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine 
• 1407830-01-6 6-(4-chlorophenyl)-1,5-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine 
• 98987-10-1 ethyl 2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-carboxylate 
• 73416-91-8 5-(2-chloroacetyl)-4-methyl-1,3,4,5-tetrahydrobenzo[b][1,4]diazepin-2-one 
• 1470407-07-8 N-{3-[(5-benzoyl-4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)carbonyl]-4-nitrophenyl}acetamide 
• 1470407-01-2 5-benzoyl-6-methyl-6,7-dihydroquinazolino[3,2-a][1,5]benzodiazepin-13(5H)-one 

Relevant academic research and scientific papers

Synthesis, Characterization, Stereochemistry and Antimicrobial Evaluation of N-Acyltetrahydrobenzodiazepin-2-ones

A few N5-substituted (1) and N1,N5-disubstituted tetrahydro-1,5-benzodiazepin-2-ones (2-8) viz. N5-chloroacetyl-, N5-formyl-, N5-dichloroacetyl-, N1,N5-diethoxycarbonyl-, N1,N5-bischloroacetyl-, N5-piperazinoacetyl- and N5-morpholinoacetyltetrahydro-1,5-benzodiazepin-2-ones have been synthesized. The characterization and conformational analysis of these compounds 2-8 have been carried out using IR and 1H, 13C, DEPT & 2D (COSY & HSQC) NMR spectral techniques. The coupling constants for compounds 3-6 were determined by irradiating the C4-methyl doublet. The appearance of major and minor conformers has been found in the case of benzodiazepin-2-ones (3 and 6) and the spectral data confirm the equilibrium due to ring inversion over the N-C=O rotation. The spectral data and the extracted coupling constant values revealed that the substituted tetrahydro-1,5-benzodiazepin-2-ones (2-8) prefer to adopt boat conformation. The antimicrobial activity of compounds 1-8 has also been evaluated.

Michael addition reaction catalyzed by imidazolium chloride to protect amino groups and construct medium ring heterocycles

An effective approach for amino protection and construction of a seven-membered ring has been developed. The method uses imidazolium chloride to carry out the Michael addition reaction at low temperatures and perform amino deprotection or construction of a seven-membered ring at high temperatures.

Metal-free tandem cyclization/hydrosilylation to construct tetrahydroquinoxalines

A one-pot tandem procedure involving cyclization and sequential hydrosilylation of imines and amides under the catalysis of B(C6F5)3 has been developed for the step-economical construction of 1,2,3,4-tetrahydroquinoxalines directly from readily available 1,2-diaminobenzenes, α-ketoesters and low-cost, safe polymethylhydrosiloxane (PMHS). This metal-free approach provides various products in good to excellent yields, and displays a wide range of substrate scope and a high degree of functional group tolerance even to reduction-sensitive moieties. The choice of hydrosilanes is critical to the catalysis, and PMHS has proved to be optimal. Decreasing the amount of PMHS could enable the reaction to stop at the 3,4-dihydroquinoxalin-2(1H)-one stage. The procedure is convenient and scalable, and neither a dried solvent nor an inert atmosphere is required. Moreover, the enantioselective construction of these products was explored, and promising results were achieved.

Synthesis of new chiral amidophosphite ligands and their application in hydrogenation of benzodiazepinones and enamides

New chiral amidophosphites were synthesized and tested in the Ir-catalyzed hydrogenation of 4-substituted 1,3-dihydro-2H-1,5-benzodiazepin-2-ones and Rh-catalyzed hydrogenation of dehydro amino acid derivatives. The triphenylphosphine additive can considerably increase the enantioselectivity of both processes.

Asymmetric Ir-catalyzed hydrogenation of 1,5-benzodiazepinones using mixtures of ligands

The catalytic hydrogenation of benzodiazepinones using metal complexes with phosphite and phosphoramidite ligands was carried out for the first time. The mixed-ligand catalytic systems containing a chiral phosphoramidite or phosphite in combination with an achiral phosphine were shown to exhibit a higher enantioselectivity compared to catalysts containing homocombinations of chiral ligands.

Discovery of Benzotriazolo[4,3-d][1,4]diazepines as Orally Active Inhibitors of BET Bromodomains

Inhibition of the bromodomains of the BET family, of which BRD4 is a member, has been shown to decrease myc and interleukin (IL) 6 in vivo, markers that are of therapeutic relevance to cancer and inflammatory disease, respectively. Herein we report substituted benzo[b]isoxazolo[4,5-d]azepines and benzotriazolo[4,3-d][1,4]diazepines as fragment-derived novel inhibitors of the bromodomain of BRD4. Compounds from these series were potent and selective in cells, and subsequent optimization of microsomal stability yielded representatives that demonstrated dose- and time-dependent reduction of plasma IL-6 in mice.

BROMODOMAIN INHIBITORS AND USES THEREOF

The present invention relates to compounds useful as inhibitors of bromodomain-containing proteins. The invention also provides pharmaceutically acceptable compositions comprising compounds of the present invention and methods of using said compositions in the treatment of various disorders.

Conformational analysis of N1,N5-diacyltetrahydro-1, 5-benzodiazepin-2-ones using NMR spectra and semiempirical MO calculations

The stereochemistry of N1,N5-diacyltetrahydro-1,5- benzodiazepin-2-ones 4 and 5 have been studied using NMR spectral techniques and semiempirical MO calculations (AMI and PM3 methods). The N1,N 5-diacetyl- and N1,N5-dibenzoyltetrahydro-4- methyl-1,5-benzodiazepin-2-ones (4 and 5, respectively) prefer boat conformations BE with endo orientations of the acyl groups at N1 and exo orientations of the acyl groups at N5 positions. The X-ray crystal structure of N1,N5-dibenzoyltetrahydro-4-methyl-1,5- benzodiazepin-2-one 5 also supported the preference for the boat conformation (BE) with endo and exo orientations of benzoyl groups at N1 and N5 positions, respectively.

Features and applications of reactions of α,β-unsaturated N-acylbenzotriazoles with amino compounds

Promoted by triethylamine, α,β-unsaturated N-acylbenzotriazoles reacted with amino compounds in a variety of ways. Thus, N-cinnamoylbenzotriazoles reacting with aromatic amines afforded novel addition products β-benzotriazolyl amides 3, which might be normally formed from the alternative but unknown 1,4-addition of benzotriazole to N-cinnamoylamides. The type 3 compounds could also result from the reaction between N-crotonoylbenzotriazole and aliphatic amines. However, normal 1,4-addition could occur between α,β-unsaturated aliphatic N-acylbenzotriazoles and aromatic amines, leading to β-amino N-acylbenzotriazoles 4 in good yields. In addition, exclusive 1,2-addition of aliphatic amines to N-cinnamoylbenzotriazoles gave excellent yields of cinnamides 5. Accordingly, three possible routes were proposed to rationalize the formation of compounds 3-5. Finally, with o-phenylenediamine and o-aminothiophenol as the substrates, the 1,4- and 1,2-addition to α,β-unsaturated N-acylbenzotriazoles could take place concurrently and the corresponding heterocycles 1,5-benzodiazepine-2-one and 1,5-benzothiazepine-4-one were constructed, respectively.

2,3,4,5-TETRAHYDRO-1H-1,5-BENZODIAZEPINE DERIVATIVE AND MEDICINAL COMPOSITION

The present invention has its object to provide a 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine derivative represented with the Formula (1) , or the pharmaceutically acceptable salt, which is effective as a therapeutic and prophylactic agent for diabetes, diabetic nephropathy, or glomerulosclerosis.