7-Bromo-5-(2-fluorophenyl)-1,3-dihydrobenzo[e]-1,4-diazepin-2-one
[CAS# 2647-50-9]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Ketone fragrance >> Aromatic ketone fragrance
• Name: 7-Bromo-5-(2-fluorophenyl)-1,3-dihydrobenzo[e]-1,4-diazepin-2-one
• Synonyms: 7-Bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one
• Molecular Formula: C₁₅H₁₀BrFN₂O
• Molecular Weight: 333.16
• CAS Registry Number: 2647-50-9
• SMILES: C1C(=O)NC2=C(C=C(C=C2)Br)C(=N1)C3=CC=CC=C3F

Properties

• Solubility: Practically insoluble (0.03 g/L) (25 °C), Calc.^*
• Density: 1.58±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 189-190 $degree
• Index of Refraction: 1.667, Calc.^*
• Boiling Point: 465.7±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 235.4±28.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

^** Okada, Yutaka

Safety Data

• Hazard Symbols: GHS02;GHS06;GHS08 Danger
• Risk Statements: H225-H301+H311+H331-H370
• Safety Statements: P210-P280-P301+P310+P330-P302+P352+P312-P304+P340+P311

Discovery and Applications

The chemical compound 7-Bromo-5-(2-fluorophenyl)-1,3-dihydrobenzo[e]-1,4-diazepin-2-one was discovered through systematic exploration in the field of medicinal chemistry. Researchers synthesized it by employing innovative synthetic methodologies and structural modifications. This compound belongs to the class of benzodiazepines, known for their diverse pharmacological activities.

7-Bromo-5-(2-fluorophenyl)-1,3-dihydrobenzo[e]-1,4-diazepin-2-one exhibits potential therapeutic effects, particularly in the treatment of neurological disorders and mental health conditions. Benzodiazepines are widely used as anxiolytics, sedatives, and muscle relaxants. This compound's unique chemical structure and pharmacological properties make it a promising candidate for the development of novel medications targeting anxiety, depression, and insomnia.

In neuroscience research, 7-Bromo-5-(2-fluorophenyl)-1,3-dihydrobenzo[e]-1,4-diazepin-2-one is utilized as a tool compound to investigate the mechanisms underlying neuronal signaling and neurotransmitter modulation. Its interaction with gamma-aminobutyric acid (GABA) receptors and other neuronal receptors provides valuable insights into the regulation of synaptic transmission and neuronal excitability. Researchers use this compound to elucidate the pathophysiology of neurological disorders and explore potential therapeutic interventions.

The discovery of 7-Bromo-5-(2-fluorophenyl)-1,3-dihydrobenzo[e]-1,4-diazepin-2-one opens avenues for drug development and lead optimization in the pharmaceutical industry. Medicinal chemists employ structure-activity relationship (SAR) studies and computational modeling techniques to optimize its pharmacokinetic and pharmacodynamic properties. This compound serves as a scaffold for the design and synthesis of analogs with improved efficacy, selectivity, and safety profiles for various therapeutic indications.

In chemical biology, 7-Bromo-5-(2-fluorophenyl)-1,3-dihydrobenzo[e]-1,4-diazepin-2-one is used to probe biological systems and elucidate molecular pathways involved in disease progression. Its ability to modulate specific targets within cellular signaling cascades enables researchers to dissect complex biological processes and identify potential drug targets. This compound facilitates the development of chemical probes and fluorescent ligands for imaging studies and drug discovery efforts.

As a potential therapeutic agent, 7-Bromo-5-(2-fluorophenyl)-1,3-dihydrobenzo[e]-1,4-diazepin-2-one undergoes preclinical and clinical evaluation to assess its safety, efficacy, and tolerability in human subjects. Clinical trials aim to validate its therapeutic benefits and determine its optimal dosage regimen for specific patient populations. The results of these trials contribute to the advancement of precision medicine and the development of innovative treatments for neurological and psychiatric disorders.

References

2022. Rationalizing the binding and α subtype selectivity of synthesized imidazodiazepines and benzodiazepines at GABAA receptors by using molecular docking studies. Bioorganic & Medicinal Chemistry Letters, 62.
DOI: 10.1016/j.bmcl.2022.128637

2018. Designer Benzodiazepines: Another Class of New Psychoactive Substances. Handbook of Experimental Pharmacology, 252.
DOI: 10.1007/164_2018_154

1977. Electronic factors in the structure-activity relationship of some 1,4-benzodiazepin-2-ones. Journal of Medicinal Chemistry, 20(9).
DOI: 10.1021/jm00219a019