194086-61-8

Basic information

• Product Name: 3,6-Dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide
• Synonyms: 2H-Thieno[3,2-e]-1,2,4-thiadiazine, 3,6-dichloro-, 1,1-dioxide;3,6-Dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide;3-Chloro-thiadiazine;Chlorothiadiazine
• CAS NO: 194086-61-8
• Molecular Formula: C₅H₂Cl₂N₂O₂S₂
• Molecular Weight: 257.12
• Mol File: 194086-61-8.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,6-Dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide(194086-61-8)
• EPA Substance Registry System: 3,6-Dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide(194086-61-8)

Safety Data

• Hazardous Substances Data: 194086-61-8(Hazardous Substances Data)

Usage

Description

3,6-Dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide is a colorless solid that belongs to the class of fused 1,2,4-thiadiazines. It is characterized by the presence of two chlorine atoms at the 3 and 6 positions, which contribute to its chemical properties and potential applications.

Uses

Used in Pharmaceutical Industry:
3,6-Dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide is used as a chemical intermediate for the preparation of fused 1,2,4-thiadiazines. These fused 1,2,4-thiadiazines are important in the development of compounds that act as openers of the KATP-regulated potassium channels. The opening of these channels can have therapeutic applications in various conditions, such as hypertension and certain types of heart diseases.
Used in Chemical Synthesis:
As a colorless solid with unique chemical properties, 3,6-Dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide can be utilized in various chemical synthesis processes. Its reactivity and structural features make it a valuable building block for the creation of novel compounds with potential applications in different industries, such as pharmaceuticals, materials science, and agrochemicals.

Upstream product

• 194086-60-7 6-chloro-2,3-dihydro-3-oxo-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide 
• 7440-44-0 pyrographite 

Downstream Products

• 319002-53-4 3-amino-6-chloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide 
• 279215-43-9 6-chloro-3-(1-methylcyclopropyl)amino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide 

Relevant articles and documents

6-Chloro-3-alkylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide derivatives potently and selectively activate ATP sensitive potassium channels of pancreatic β-cells

6-Chloro-3-alkylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide derivatives were synthesized and characterized as activators of adenosine 5′-triphosphate (ATP) sensitive potassium (KATP) channels in the β-cells by measuring effects on membrane potential and insulin release in vitro. The effects on vascular tissue in vitro were measured on rat aorta and small mesenteric vessels. Selected compounds were characterized as competitive inhibitors of [3H]glibenclamide binding to membranes of HEK293 cells expressing human SUR1/Kir6.2 and as potent inhibitors of insulin release in isolated rat islets. 6-Chloro-3-(1-methylcyclobutyl)amino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (54) was found to bind and activate the SUR1/Kir6.2 KATP channels in the low nanomolar range and to be at least 1000 times more potent than the reference compound diazoxide with respect to inhibition of insulin release from rat islets. Several compounds, e.g., 3-propylamino- (30), 3-isopropylamino- (34), 3-(S)-sec-butylamino- (37), and 3-(1-methylcyclopropyl)amino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (53), which were found to be potent and β-cell selective activators of KATP channels in vitro, were found to inhibit insulin secretion in rats with minimal effects on blood pressure and to exhibit good oral pharmacokinetic properties.