360-81-6

Basic information

• Product Name: 3-Methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide
• Synonyms: 3-Methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide;3-Methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide;Mebetide;3-methyl-4H-1λ6,2,4-benzothiadiazine 1,1-dioxide
• CAS NO: 360-81-6
• Molecular Formula: C₈H₈N₂O₂S
• Molecular Weight: 196.2263
• Mol File: 360-81-6.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 376.2°Cat760mmHg
• Flash Point: 181.3°C
• Appearance: /
• Density: 1.47g/cm³
• Vapor Pressure: 7.36E-06mmHg at 25°C
• Refractive Index: 1.674
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 3-Methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide(360-81-6)
• EPA Substance Registry System: 3-Methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide(360-81-6)

Safety Data

• Hazardous Substances Data: 360-81-6(Hazardous Substances Data)

Usage

Uses

3-Methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide functions in structure activity relations analysis of benzothiadiazine compounds as hyperglycemic agents by correlating with the reduction in urine output in vivo and insulin production both in vivo and in vitro. Also functions as an antihypertensive agent.

InChI:InChI=1/C8H8N2O2S/c1-6-9-7-4-2-3-5-8(7)13(11,12)10-6/h2-5H,1H3,(H,9,10)

Upstream product

• 13338-00-6 2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide 
• 108-24-7 acetic anhydride 
• 23530-44-1 N-((2-nitrophenyl)sulfonyl)acetamide 
• 92748-09-9 2-bromobenzene-1-sulfonamide 
• 124-42-5 acetamidine hydrochloride 
• 1327160-59-7 N-((2-fluorophenyl)sulfonyl)ethanimidamide 
• 1327160-60-0 N-[(2-chlorophenyl)sulfonyl]ethanimidamide 
• 1310552-54-5 N-[(2-bromophenyl)sulfonyl]ethanimidamide 
• 2905-21-7 2-fluorobenzenesulfonyl chloride 
• 2905-23-9 2-chlorophenylsulfonyl chloride 
• 69943-39-1 2-(acetylamino)benzenesulfonamide 
• 127-19-5 N,N-dimethyl acetamide 
• 3306-62-5 2-AMINOBENZENESULFONAMIDE 
• 2905-25-1 o-bromobenzenesulfonyl chloride 

Downstream Products

• 364-98-7 diazoxide 

Relevant articles and documents

Synthesis and in vitro antileishmanial efficacy of novel benzothiadiazine-1,1-dioxide derivatives

Leishmaniasis is a major vector-borne parasitic disease that affects thousands of people in tropical and subtropical developing countries. In 2019 alone, it killed 26,000–65,000 individuals. Leishmaniasis is curable, yet its eradication and elimination are hampered by major hurdles, such as the availability of only a handful of clinical toxic drugs and the emergence of pathogenic resistance against them. This underscores the imperative need for new and effective antileishmanial drugs. In search for such agents, we synthesized and evaluated the in vitro antileishmanial potential of a small library of benzothiadiazine derivatives by assessing their activity against the promastigotes of three strains of Leishmania and toxicity in healthy cells. The derivatives were found to have no toxicity to the mammalian cells and were, in general, active against all parasites. The benzothiadiazine derivative 1e, 3-methyl-2-[3-(trifluoromethyl)benzyl]-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide, was found to be the most active (IC50, 0.2 μM) against Leishmania major, responsible for the most prevalent disease form, cutaneous leishmaniasis. Conversely, benzothiadiazine 2c, 2-(4-bromobenzyl)-3-phenyl-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide, was the most potent (IC50, 6.5 μM) against Leishmania donovani, a causative strain of the lethal visceral leishmaniasis. Both compounds stand as antipromastigote hits for further lead investigation into their potential to act as new antileishmanial agents.

Coumarins and other fused bicyclic heterocycles with selective tumor-associated carbonic anhydrase isoforms inhibitory activity

Herein we report for the first time a series of 2-benzamido-N-(2-oxo-4-(methyl/trifluoromethyl)-2H-chromen-7-yl) benzamide 3a–f and substituted quinazolin-4(3H)-ones and 2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxides (5, 6, 8 and 10a–c) as selective inhibitors of the tumor associated hCA IX and XII isoforms. Among the compounds reported the trifluoromethyl derivative 3d resulted the most potent against these CA isoforms with KIs of 10.9 and 6.7?nM.

Facile synthesis of 4H-1,2,4-benzothiadiazine-1,1-dioxides

o-Bromoarylsulfonylated amidines prepared either by acylation of amidine with o-bromoarylsulfonyl chloride or through the reaction of o-bromoarylsulfoamide with lactime ether underwent Cu(I)-catalyzed intramolecular cyclization to give 4H-1,2,4-benzothiadiazine-1,1-dioxides in good yield. By varying substituents on arylsulfonyl moieties, amidines, and lactime ethers, a small library of structurally diverse 4H-1,2,4- benzothiadiazine-1,1-dioxide derivatives was prepared.