14141-71-0

Basic information

• Product Name: 7-BROMO-2H-1,2,4-BENZOTHIADIAZIN-3(4H)-ONE 1,1-DIOXIDE
• Synonyms: 7-BROMO-2H-1,2,4-BENZOTHIADIAZIN-3(4H)-ONE 1,1-DIOXIDE;2H-1,2,4-BENZOTHIADIAZIN-3(4H)-ONE, 7-BROMO, 1,1-DIOXIDE;7-broMo-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide
• CAS NO: 14141-71-0
• Molecular Formula: C₇H₅BrN₂O₃S
• Molecular Weight: 277.1
• Mol File: 14141-71-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 335 °C
• Appearance: /
• Density: 1.877±0.06 g/cm3(Predicted)
• PKA: 4.38±0.20(Predicted)
• CAS DataBase Reference: 7-BROMO-2H-1,2,4-BENZOTHIADIAZIN-3(4H)-ONE 1,1-DIOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-BROMO-2H-1,2,4-BENZOTHIADIAZIN-3(4H)-ONE 1,1-DIOXIDE(14141-71-0)
• EPA Substance Registry System: 7-BROMO-2H-1,2,4-BENZOTHIADIAZIN-3(4H)-ONE 1,1-DIOXIDE(14141-71-0)

Safety Data

• Hazardous Substances Data: 14141-71-0(Hazardous Substances Data)

Usage

General Description

7-BROMO-2H-1,2,4-BENZOTHIADIAZIN-3(4H)-ONE 1,1-DIOXIDE is a chemical compound with the formula C7H4BrN2O3S. It is a heterocyclic compound with a benzothiadiazine backbone and a bromine atom attached to the 7th position. The 1,1-dioxide functional group is also present in the molecule. 7-BROMO-2H-1,2,4-BENZOTHIADIAZIN-3(4H)-ONE 1,1-DIOXIDE is often used in the field of pharmaceuticals and agrochemicals as a building block in the synthesis of various biologically active compounds. It may also possess potential pharmacological and therapeutic properties due to its structural features. Additionally, it has been studied for its potential as a corrosion inhibitor in industrial applications.

Upstream product

• 54734-84-8 2-amino-5-bromobenzenesulfonamide 
• 57-13-6 urea 
• 13338-00-6 2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 106-40-1 4-bromo-aniline 
• 3306-62-5 2-AMINOBENZENESULFONAMIDE 

Downstream Products

• 54734-84-8 2-amino-5-bromobenzenesulfonamide 
• 716353-94-5 C₃₆H₄₀N₆O₄S 

Relevant articles and documents

Discovery of Halogenated Benzothiadiazine Derivatives with Anticancer Activity**

Mitochondrial respiratory complex II (CII), also known as succinate dehydrogenase, plays a critical role in mitochondrial metabolism. Known but low potency CII inhibitors are selectively cytotoxic to cancer cells including the benzothiadiazine-based anti-hypoglycemic diazoxide. Herein, we study the structure-activity relationship of benzothiadiazine derivatives for CII inhibition and their effect on cancer cells for the first time. A 15-fold increase in CII inhibition was achieved over diazoxide, albeit with micromolar IC50 values. Cytotoxicity evaluation of the novel derivatives resulted in the identification of compounds with much greater antineoplastic effect than diazoxide, the most potent of which possesses an IC50 of 2.93±0.07 μM in a cellular model of triple-negative breast cancer, with high selectivity over nonmalignant cells and more than double the potency of the clinical agent 5-fluorouracil. No correlation between cytotoxicity and CII inhibition was found, thus indicating an as-yet-undefined mechanism of action of this scaffold. The derivatives described herein represent valuable hit compounds for therapeutic discovery in triple-negative breast cancer.

"a Sweet Combination": Developing Saccharin and Acesulfame K Structures for Selectively Targeting the Tumor-Associated Carbonic Anhydrases IX and XII

The sweeteners saccharin (SAC) and acesulfame K (ACE) recently entered the topic of anticancer human carbonic anhydrase (CA, EC 4.2.1.1) inhibitors, as they showed to selectively inhibit the tumor-associated CAs IX/XII over ubiquitous CAs. A drug design s

Novel 4,4-disubstituted piperidine-based C-C chemokine receptor-5 inhibitors with high potency against human immunodeficiency virus-1 and an improved human ether-a-go-go related gene (hERG) profile

We recently described (J. Med. Chem. 2008, 51, 6538-6546) a novel class of CCR5 antagonists with strong anti-HIV potency. Herein, we detail SAR converting leads 1 and 2 to druglike molecules. The pivotal structural motif enabling this transition was the secondary sulfonamide substituent. Further finetuning of the substituent pattern in the sulfonamide paved the way to enhancing potency and bioavailability and minimizing hERG inhibition, resulting in discovery of clinical compound 122 (GSK163929).