104873-98-5

Usage

Uses

Used in Pharmaceutical Industry:
(3S)-3-METHYL-1,4-BENZODIAZEPINE-2,5-DIONE is used as a sedative and anxiolytic agent for the treatment of anxiety disorders and insomnia. Its efficacy is attributed to its ability to enhance the inhibitory signaling of GABA, leading to a calming effect on the central nervous system. Due to its potential for abuse, it is classified as a controlled substance, emphasizing the importance of medical supervision during its administration.

InChI:InChI=1/C10H10N2O2/c1-6-9(13)12-8-5-3-2-4-7(8)10(14)11-6/h2-6H,1H3,(H,11,14)(H,12,13)/t6-/m0/s1

Upstream product

• 68790-38-5 2-(tert-butyloxycarbonylamino)benzoic acid 
• 2224-52-4 L-alanine N-carboxyanhydride 
• 118-48-9 isatoic anhydride 
• 1115-59-9 (S)-alanine ethyl ester hydrochloride 
• 14683-53-5 2-amine-N-[(S)-methoxycarbonylethyl]benzamide 
• 56-41-7 L-alanin 
• 34897-85-3 o-azidobenzoyl chloride 
• 769120-97-0 (S)-2-(2-Amino-benzoylamino)-propionic acid ethyl ester 

Relevant academic research and scientific papers

Improved method for microwave-assisted synthesis of benzodiazepine-2,5-diones from isatoic anhydrides mediated by glacial acetic acid

An improved and simpler method for the synthesis of benzodiazepin-2,5-diones and 7-iodobenzodiazepin-2,5-diones catalyzed by glacial acetic acid using isatoic anhydride and 6-iodoisatoic anhydride, respectively, as starting materials is reported. The target products were achieved in good yields (up to 71percent) using microwave irradiation as the activating mode of reaction in the presence of acetic acid instead of the traditional polar aprotic solvents as dimethylformamide (DMF), dimethyl sulfoxide (DMSO) or dimethylacetamide (DMAC). Moreover, relatively simple purification workup is required. The optimal temperature to obtain the benzodiazepin-2,5-dione derivatives was 130 °C, while the best irradiation time was 3 min. In addition, the methodology for the selective preparation of 6-iodoisatoic anhydride with an overall yield of 62percent is presented. Printed in Brazil-

Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate-Directed Formation of Quinolones versus Quinazolinones

Previous studies showed that the FeII/α-ketoglutarate dependent dioxygenase AsqJ induces a skeletal rearrangement in viridicatin biosynthesis in Aspergillus nidulans, generating a quinolone scaffold from benzo[1,4]diazepine-2,5-dione substrates. We report that AsqJ catalyzes an additional, entirely different reaction, simply by a change in substituent in the benzodiazepinedione substrate. This new mechanism is established by substrate screening, application of functional probes, and computational analysis. AsqJ excises H2CO from the heterocyclic ring structure of suitable benzo[1,4]diazepine-2,5-dione substrates to generate quinazolinones. This novel AsqJ catalysis pathway is governed by a single substituent within the complex substrate. This unique substrate-directed reactivity of AsqJ enables the targeted biocatalytic generation of either quinolones or quinazolinones, two alkaloid frameworks of exceptional biomedical relevance.

Facile synthesis of 1,4-benzodiazepine-2,5-diones and quinazolinones from amino acids as anti-tubercular agents

A family of 1,4-benzodiazepine-2,5-diones and quinazolinones with diverse substituents at the C-3 position were synthesized via a novel, simple and convenient methodology using H2PtCl6 as the catalyst. The substitution at the C-3 pos

Low-valent titanium-mediated enantioselective synthesis of quinazolinone alkaloids circumdatins F, H, and analogs

We report the concise and protecting-group-free enantioselective total syntheses of circumdatins F and H. In view of the extreme importance of analogs of quinazolinone alkaloids in drug research and discovery, four analogs of bioactive quinazolinobenzodiazepine alkaloids, including demethoxycircumdatin H (12) and N-demethylbenzomalvin A (13), have been synthesized. The method is based on the low-valent titanium-promoted intramolecular reductive coupling of imides with o-nitrobenzimides, which yielded quinazolino[3,2-a][1,4]benzodiazepines under mild conditions. In addition, heptacyclic dehydraasperlicin E (16) has been synthesized from asperlicin C by a NCS-mediated dehydra-cyclization reaction.

Identification of the benzodiazepines as a new class of antileishmanial agent

The continual increase in drug resistance; the lack of new chemotherapeutic agents; the toxicity of existing agents and the increasing morbidity with HIV co-infection mean the search for new antileishmanial agents has never been more urgent. We have ident

One pot conversion of azido arenes to N-arylacetamides and N-arylformamides: Synthesis of 1,4-benzodiazepine-2,5-diones and fused [2,1-b]quinazolinones

Sodium iodide in acidic media has been employed for the synthesis of N-arylformamides and N-arylacetamides. The NaI/acetic acid reagent system has also been extended for the synthesis of 1,4-benzodiazepine-2,5-diones, pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones, and fused [2,1-b]quinazolinones.

Cycloalkyl[b][1,4]benzodiazepinoindoles are agonists at the human 5-HT 2C receptor

Evaluation of selected compounds from our Corporate Compound Library in a human 5-HT2C receptor binding assay led to the discovery of WAY-629, a cyclohexyl[b][1,4]benzodiazepinoindole (Ki 56nM, Emax 90%), which is selectiv

[1,4]Diazepino [6,7,1-jk] carbazoles and derivatives

This invention provides [1,4]diazepino[6,7,1-jk]carbazole compounds of the formula: wherein: R1 and R2 are H, alkyl, alkoxy, halogen, fluorinated alkyl, —CN, —NH—SO2-alkyl, —SO2—NH-alkyl, alkyl amide, amino, alkylamino, dialkylamino, fluorinated alkoxy, acyl, phenoyl or thiophenoyl; R3, R4, R5 and R6 are H, alkyl, cycloalkyl, alkoxy or cycloalkoxy; R7 is H or alkyl; R8 is H or alkyl; and the dashed line indicates an optional double bond; or a pharmaceutically acceptable salt thereof, as well as methods and pharmaceutical compositions utilizing them for the treatment or prevention of disorders such as obsessive-compulsive disorder, depression, anxiety, schizophrenia, migraine, sleep disorders, eating disorders, obesity, epilepsy, and spinal cord injury.

New routes to 1,4-benzodiazepin-2,5-diones

1,4-benzodiazepin-2,5-diones have been synthesized in good overall yields by two routes, the first one by cyclisation of dipeptides prepared from Boc anthranilic acid and α-amino acid methyl esters, the second one by reaction of N-carboxy α-amino acid anhydrides with Boc anthranilic acid.