877265-23-1

Basic information

• Product Name: 6-BROMO-1,2-BENZOTHIAZOLE
• Synonyms: 6-BROMO-1,2-BENZOTHIAZOLE;6-Bromobenzo[d]isothiazole
• CAS NO: 877265-23-1
• Molecular Formula: C7H4BrNS
• Molecular Weight: 214.08236
• Mol File: 877265-23-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 6-BROMO-1,2-BENZOTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-1,2-BENZOTHIAZOLE(877265-23-1)
• EPA Substance Registry System: 6-BROMO-1,2-BENZOTHIAZOLE(877265-23-1)

Safety Data

• Hazardous Substances Data: 877265-23-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-BROMO-1,2-BENZOTHIAZOLE is used as a key intermediate in the synthesis of 4-heteroaryl 1,2,3,4-tetrahydroisoquinolines, which are known as triple re-uptake inhibitors. These inhibitors are significant in the development of medications for the treatment of neurological and psychiatric disorders, as they can simultaneously target the reuptake of multiple neurotransmitters, leading to enhanced therapeutic effects.
Used in Organic Synthesis:
6-BROMO-1,2-BENZOTHIAZOLE is also utilized as a versatile reagent in organic synthesis, particularly for the preparation of various heterocycles and complex organic molecules. Its unique structure allows for a wide range of chemical reactions, making it a valuable building block in the creation of new compounds with potential applications in various fields, such as materials science, agrochemicals, and pharmaceuticals.

Upstream product

• 57848-46-1 4-bromo-2-fluorobenzaldehyde 

Downstream Products

• 97050-36-7 benzo[d]isothiazol-6-amine 
• 1104071-55-7 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]isothiazole 

Relevant articles and documents

From High-Throughput Screening to Target Validation: Benzo[ d]isothiazoles as Potent and Selective Agonists of Human Transient Receptor Potential Cation Channel Subfamily M Member 5 Possessing in Vivo Gastrointestinal Prokinetic Activity in Rodents

Transient receptor potential cation channel subfamily M member 5 (TRPM5) is a nonselective monovalent cation channel activated by intracellular Ca2+ increase. Within the gastrointestinal system, TRPM5 is expressed in the stoma, small intestine, and colon. In the search for a selective agonist of TRPM5 possessing in vivo gastrointestinal prokinetic activity, a high-throughput screening was performed and compound 1 was identified as a promising hit. Hit validation and hit to lead activities led to the discovery of a series of benzo[d]isothiazole derivatives. Among these, compounds 61 and 64 showed nanomolar activity and excellent selectivity (>100-fold) versus related cation channels. The in vivo drug metabolism and pharmacokinetic profile of compound 64 was found to be ideal for a compound acting locally at the intestinal level, with minimal absorption into systemic circulation. Compound 64 was tested in vivo in a mouse motility assay at 100 mg/kg, and demonstrated increased prokinetic activity.

Amino-substituted heterocycles, compositions thereof, and methods of treatment therewith

Provided herein are Heterocyclic Compounds having the following structure: wherein R1, R2, X, Y and Z are as defined herein, compositions comprising an effective amount of a Heterocyclic Compound and methods for treating or preventing cancer, inflammatory conditions, immunological conditions, metabolic conditions and conditions treatable or preventable by inhibition of a kinase pathway comprising administering an effective amount of a Heterocyclic Compound to a patient in need thereof.