360-81-6

Usage

Uses

Used in Pharmaceutical Industry:
3-Methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide is used as a hyperglycemic agent for the treatment of diabetes. It helps in reducing urine output and increasing insulin production both in vivo and in vitro, which aids in managing blood sugar levels in diabetic patients.
Used in Cardiovascular Applications:
In the field of cardiovascular medicine, 3-Methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide is utilized as an antihypertensive agent. It assists in lowering blood pressure, which is crucial for individuals suffering from hypertension and other related cardiovascular conditions.
These applications highlight the potential of 3-Methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide in addressing significant health concerns, such as diabetes and hypertension. Further research and development in these areas could lead to the discovery of more effective treatments and therapies for these conditions.

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 
• 1085853-26-4 N'-(2-bromobenzenesulfonyl)-2-(trimethylsilyl)acetamidine 
• 127-19-5 N,N-dimethyl acetamide 
• 3306-62-5 2-AMINOBENZENESULFONAMIDE 
• 2905-23-9 2-chlorophenylsulfonyl chloride 
• 2905-21-7 2-fluorobenzenesulfonyl chloride 
• 1310552-54-5 N-[(2-bromophenyl)sulfonyl]ethanimidamide 
• 1327160-60-0 N-[(2-chlorophenyl)sulfonyl]ethanimidamide 
• 1327160-59-7 N-((2-fluorophenyl)sulfonyl)ethanimidamide 
• 2905-25-1 o-bromobenzenesulfonyl chloride 
• 1310552-54-5 N-(1-aminoethylidene)-2-bromobenzenesulfonamide 
• 92748-09-9 2-bromobenzene-1-sulfonamide 
• 124-42-5 acetamidine hydrochloride 

Downstream Products

• 364-98-7 diazoxide 

Relevant academic research and scientific papers

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.

Method for preparing diazoxide

The invention discloses a method for preparing diazoxide. The method comprises the following steps: reacting o-aminobenzenesulfonamide with N-chlorosuccinimide in a chlorine solvent to obtain 2-amino-5-chlorobenzenesulfonamide, mixing the 2-amino-5-chlorobenzenesulfonamide, an imidazolium salt and an amide solvent, and heating the obtained mixture to react to obtain the diazoxide; or mixing o-aminobenzenesulfonamide, the imidazolium salt and the amide solvent, heating for a reaction to obtain a compound IV, and reacting the compound IV with N-chlorosuccinimide in the chlorine solvent so as toobtain the diazoxide. The invention also discloses an application of imidazole hydrochloride as a catalyst in the preparation of diazoxide. The method avoids the problems that chlorosulfonyl isocyanate and strong acid (sulfuric acid) which have high corrosivity and toxicity are used in the reaction process and the reaction temperature is high (240-250 DEG C), and the reaction steps are short; thetotal yield of the two steps can reach 90% or above; and compared with publicly reported diazoxide preparation methods, the synthesis method of the invention overcomes numerous defects, so that the synthesis method is suitable for industrial production.

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.

A one-pot, non-catalytic approach to 1,2,4-benzothiadiazine-1,1-dioxides

Condensations of o-halo-substituted benzenesulfonyl chlorides with 2-aminopyridines and amidines may give the corresponding 1,2,4-benzothiadiazine- 1,1-dioxides under mild, non-catalytic conditions in nearly quantitative yields. The successful one-pot cyclization depends on three factors: (i) the nature of the o-halogen, (ii) the electronic character of the benzene ring substituent, and (iii) the steric load around the amidine unit. O-Fluorobenzenesulfonyl chlorides bearing methylcarboxyl- or nitro-group and o-chloro- and o-bromobenzenesulfonyl chlorides bearing nitro-group are reactive enough to give the desired 1,2,4-benzothiadiazine-1,1-dioxides in a one-pot base-promoted reaction. In all other cases, open-chain sulfonylated amidine intermediates are isolated. The latter are converted to the title compounds either in the presence of potassium carbonate or upon the addition of a copper(I) catalyst.

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.

Copper-Catalyzed Synthesis of 1,2,4-Benzothiadiazine 1,1-Dioxide Derivatives by coupling of 2-Halobenzenesulfonamides with amidines

We have developed a simple and practical copper-catalyzed method for the synthesis of 1,2,4-benzothiadiazine 1,1-dioxide derivatives via cascade reactions of substituted 2-halobenzenesulfonamides with amidines, and the method is of value for the construction of this kind of molecules with biological and medicinal activities.

Synthetic utility of ammonium salts in a Cu-catalyzed three-component reaction as a facile coupling partner

(Chemical Equation Presented) Ammonium salts were found to be a convenient and inexpensive reagent in the Cu-catalyzed three-component reaction with terminal alkynes and sulfonyl or phosphoryl azides leading to N-unprotected amidines. Thus obtained amidines bearing 2-bromobenzenesulfonyl moiety were efficiently cyclized by the Cu-catalyzed intramolecular N-arylation to give an important pharmacophore skeleton of 2H-1,2,4-benzothiadiazine 1,1-dioxides. Conveniently, two tandem catalytic procedures could be readily operated in one pot.

A comparison of ring-chain tautomerism in heterocycles derived from 2-aminobenzenesulfonamide and anthranilamide

A number of anthranilamide and 2-aminobenzenesulfonamide derivatives with aromatic aldehydes and 1,3-dicarbonyl compounds were synthesized. Substituted benzaldehyde derivatives of neither aminoamides showed tautomerism in solutions. Reaction products of 2-aminobenzenesulfonamide with p-substituted benzoylacetic aldehydes and p-substituted benzoylacetones undergo ring-chain tautomerism with a good linear correlation between the ring-chain equilibrium constants (log K, where K=[ring]/[chain]) and the Hammett-Brown σ+ parameters of the aromatic substituents. The equilibrium constant was measured for the reaction products of 2-aminobenzenesulfonamide with unsubstituted benzoylacetaldehyde at several temperatures which enabled the enthalpy and entropy of this reaction to be evaluated.

Novel compounds and their use as positive AMPA receptor modulators

The invention provides novel compounds represented by the general formula 5 compound represented by the formula: wherein the bond represented by the broken line may be a single, a double bond or absent; and if the bond is absent, then the nitrogen is substituted with a hydrogen and R2; X represents SO2 or C═O or CH2; Y represents —CH(R4)—, —N(R4)— or —N(R4)—CH2—, O; and the meaning of R2, R3, R4, R5, R6, R7, and R8 are as defined in the application The compounds are useful as positive modulators of the AMPA-receptor.

Synthesis and pharmacological evaluation of 1,2,4-benzothiadiazin-1,1- dioxides bearing 5- or 7-sulfonylurea moieties

A series of substituted benzothiadiazin-1,1-dioxides bearing sulfonylurea moieties in position 5 or 7 has been synthesized. The most powerful vasodilator compound was 18a, obtained by substitution of a sulfonylurea moiety on position 7 of the diazoxide skeleton by means of a SO2 group. Interestingly, 18a and 18b were found inactive on insulin secretion at 50 μM and likely devoid of adverse effect on glycemia, suggesting a special therapeutic potential for these compounds.