104874-01-3

Usage

Uses

Used in Pharmaceutical Industry:
(3S)-3-Isobutyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione is used as a central nervous system depressant for the treatment of anxiety, insomnia, and panic disorders due to its similar pharmacological effects as other benzodiazepines.

Upstream product

• 118-48-9 isatoic anhydride 
• 328-39-2 LEUCINE 
• 64-19-7 acetic acid 
• 857602-04-1 N-(2-bromo-4-methyl-valeryl)-anthranilic acid 
• 2743-40-0 L-leucine ethyl ester hydrochloride 
• 34897-85-3 o-azidobenzoyl chloride 
• 61-90-5 L-leucine 
• 7517-19-3 methyl (L)-leucinate hydrochloride 
• 118-92-3 anthranilic acid 
• 24919-33-3 N-(2-nitrobenzoyl)leucine 

Relevant academic research and scientific papers

One-Pot Synthesis of Trifluoromethylated Quinazolin-4(3 H)-ones with Trifluoroacetic Acid as CF3 Source

A novel and convenient one-pot sequential cascade method for the preparation of 2-trifluoromethylquinazolin-4(3H)-ones is described. Trifluoroacetic acid (TFA) was employed as inexpensive and readily available CF3 source, which in the presence

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

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-

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.

A facile synthesis of quinazolino[1,4]benzodiazepine alkaloids via reductive N-heterocyclization of N-(2-nitrobenzoyl)amides: Total synthesis of asperlicin C, circumdatin H, and analogues

A facile and short synthesis of a series of quinazolino[1,4]benzodiazepine alkaloids, including asperlicin C, circumdatin H and some analogues, is reported utilizing coupling of readily available [1,4]benzodiazepine with 2-nitrobenzoyl chlorides, followed by a reductive N-heterocyclization. ARKAT USA, Inc.

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

BENZODIAZEPINE AND BENZOPIPERAZINE ANALOG INHIBITORS OF HISTONE DEACETYLASE

This invention relates to compounds for the inhibition of histone deacetylase More particularly, the invention provides for compounds of formula (I): wherein A, B, D, E, X1, X2, X3, X4 and n are as defined in the specification A method of inhibiting histone deacetylase in a cell, the method comprising contacting the cell with a compound of formula (I), in an amount sufficient to inhibit histone deacetylase, is also disclosed.

Simple synthesis, structure and ab initio study of 1,4-benzodiazepine-2,5- diones

A simple procedure for the synthesis of pyrido[2,1-c][1,4] benzodiazepine-6,12-dione (1) and 1,4-benzodiazepine-2,5-diones (2a-2d), using microwave irradiation and/or conventional heating is reported. The configuration of 1 was determined by single-crysta

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.