7-Bromo-1-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one
[CAS# 913297-44-6]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 7-Bromo-1-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one
• Synonyms: 4-bromo-3-methyl-1H-benzimidazol-2-one
• Molecular Formula: C₈H₇BrN₂O
• Molecular Weight: 227.06
• CAS Registry Number: 913297-44-6
• EC Number: 958-672-4
• SMILES: CN1C2=C(C=CC=C2Br)NC1=O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

7-Bromo-1-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one is a synthetic compound with potential pharmacological applications characterized by a benzimidazolone core substituted with bromine atoms and methyl groups. The exploration of benzimidazolone derivatives began in the mid-20th century, driven by their structural similarity to natural alkaloids with a variety of biological activities. The bromine atom at position 7 and the methyl group at position 1 of the benzimidazolone core were introduced to enhance the pharmacological properties of the compound, including its binding affinity to specific protein targets. The synthesis of 7-bromo-1-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one was designed to optimize these properties for therapeutic use. The bromine atom enhances the compound's ability to interact with biological targets, contributing to its pharmacological effects. The benzimidazolone core provides stability and biological activity, forming the backbone of many biologically active compounds.

The compound has been studied for its potential to modulate neural activity. Its structure enables it to interact with neurotransmitter receptors, showing promise for treating conditions such as anxiety and epilepsy. It exerts its therapeutic potential by acting on specific ion channels or receptors in the central nervous system (CNS). The compound's ability to modulate cell signaling pathways makes it a candidate for the development of anti-inflammatory drugs. It may inhibit the production of proinflammatory cytokines, thereby reducing inflammation in conditions such as rheumatoid arthritis and inflammatory bowel disease.

In chemical biology, it is used to study protein-ligand interactions. The compound's structure provides a useful scaffold for probing the function of various proteins, particularly those involved in signal transduction and enzymatic activity. Its selective binding characteristics allow it to be used as a molecular probe to study biological pathways and receptor function in cell models.

The compound serves as a lead structure in drug development, providing a basis for the design of new analogs with improved efficacy and safety. Modifications to its core structure can produce derivatives with enhanced biological activity against specific targets. It is used in structure-activity relationship (SAR) studies to identify key structural features responsible for biological activity, guiding the design of more potent and selective drug candidates.

References

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