17972-72-4

Usage

Uses

Used in Pharmaceutical Industry:
7-Bromo-5-phenyl-1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-one is used as a key intermediate in the synthesis of inhibitors for Shiga toxin. Shiga toxin is a potent bacterial toxin produced by certain strains of Escherich as well as other bacteria, which can cause severe diseases such as hemolytic uremic syndrome and bloody diarrhea. 7-BROMO-5-PHENYL-1,3,4,5-TETRAHYDRO-2H-1,4-BENZODIAZEPIN-2-ONE plays a crucial role in the development of therapeutic agents that can effectively inhibit the activity of Shiga toxin, thereby preventing the progression of these life-threatening diseases.
In addition to its use in the synthesis of Shiga toxin inhibitors, 7-bromo-5-phenyl-1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-one can also be utilized in the development of other pharmaceutical agents with potential applications in various therapeutic areas. The benzodiazepine core of 7-BROMO-5-PHENYL-1,3,4,5-TETRAHYDRO-2H-1,4-BENZODIAZEPIN-2-ONE provides a versatile scaffold for the design and synthesis of novel drugs with improved pharmacological properties and therapeutic efficacy.
Overall, 7-bromo-5-phenyl-1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-one is a valuable chemical entity with significant potential in the pharmaceutical industry. Its unique structural features and diverse applications make it an important compound for further research and development in the field of drug discovery and medicinal chemistry.

Upstream product

• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 39859-36-4 2-amino-5-bromobenzophenone 
• 17972-71-3 N-(2-benzoyl-4-bromophenyl)-2-bromoacetamide 
• 98-88-4 benzoyl chloride 
• 106-40-1 4-bromo-aniline 
• 2894-61-3 7-bromo-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one 

Downstream Products

• 313683-81-7 7-bromo-5-phenyl-4-propionyl-1,3,4,5-tetrahydro-2H-benzo[e][1,4]diazepin-2-one 

Relevant academic research and scientific papers

Structure-Activity Relationship Studies of Retro-1 Analogues against Shiga Toxin

High-throughput screening has shown that Retro-1 inhibits ricin and Shiga toxins by diminishing their intracellular trafficking via the retrograde route, from early endosomes to the Golgi apparatus. To improve the activity of Retro-1, a structure-activity relationship (SAR) study was undertaken and yielded an analogue with a roughly 70-fold better half-maximal effective concentration (EC50) against Shiga toxin cytotoxicity measured in a cell protein synthesis assay.

Retro-1-oligonucleotide conjugates. Synthesis and biological evaluation

Addition of small molecule Retro-1 has been described to enhance antisense and splice switching oligonucleotides. With the aim of assessing the effect of covalently linking Retro-1 to the biologically active oligonucleotide, three different derivatives of Retro-1 were prepared that incorporated a phosphoramidite group, a thiol or a 1,3-diene, respectively. Retro-1–oligonucleotide conjugates were assembled both on-resin (coupling of the phosphoramidite) and from reactions in solution (Michael-type thiol-maleimide reaction and Diels-Alder cycloaddition). Splice switching assays with the resulting conjugates showed that they were active but that they provided little advantage over the unconjugated oligonucleotide in the well-known HeLa Luc705 reporter system.

COMPOUNDS WHICH HAVE A PROTECTIVE ACTIVITY WITH RESPECT TO THE ACTION OF TOXINS AND OF VIRUSES WITH AN INTRACELLULAR MODE OF ACTION

The subject matter of the present invention is novel families of compounds which are aromatic amine, imine, aminoadamantane and benzodiazepine derivatives, medicaments comprising same and the use thereof as inhibitors of the toxic effects of toxins with intracellular activity, such as, for example, ricin, and of viruses that use the internalization pathway for infecting cells.

Benzodiazepine Derivatives for Use in the Treatment of Chlamydiales Infections

The invention relates to a method for treating a Chlamidyales infection comprising the administration of a therapeutically effective amount of a compound of formula (I) to a subject in need thereof: Wherein R1, R2, R3 and

Synthesis, Chiral Separation, Absolute Configuration Assignment, and Biological Activity of Enantiomers of Retro-1 as Potent Inhibitors of Shiga Toxin

The Shiga toxin (Stx) family is composed of related protein toxins produced by the bacteria Shigella dysenteriae and certain pathogenic strains of E.coli. No effective therapies for Stx intoxication have been developed yet. However, inhibitors that act on the intracellular trafficking of these toxins may provide new options for the development of therapeutic strategies. This study reports the synthesis, chromatographic separation, and pharmacological evaluation of the two enantiomers of Retro-1, a compound active against Stx and other such protein toxins. Retro-1 works by inhibiting retrograde transport of these toxins inside cells. In vitro experiments proved that the configuration of the stereocenter at position 5 is not crucial for the activity of this compound. X-ray diffraction data revealed (S)-Retro-1 to be slightly more active than (R)-Retro-1.

INHIBITORS OF THE SHIGA TOXINS TRAFFICKING THROUGH THE RETROGRADE PATHWAY

The present invention relates to the use of compounds of general formula (I) and (II) for the preparation of a drug for preventing and/or treating disorders caused by Shiga toxins and related toxins.