359-85-3

Usage

Uses

Used in Pharmaceutical Industry:
2H-1,2,4-Benzothiadiazine 1,1-dioxide is used as a diuretic agent for the treatment of high blood pressure and fluid retention. It functions by promoting the excretion of sodium and water, which leads to a decrease in blood volume and consequently a reduction in blood pressure.
It is important for patients to adhere to the dosage and directions provided by a healthcare professional when taking bendroflumethiazide to ensure its effectiveness and minimize potential side effects. Additionally, individuals with severe kidney impairment or those allergic to sulfonamide-derived drugs should not use this medication.

InChI:InChI=1/C7H6N2O2S/c10-12(11)7-4-2-1-3-6(7)8-5-9-12/h1-5H,(H,8,9)

Upstream product

• 50-00-0 formaldehyd 
• 3306-62-5 2-AMINOBENZENESULFONAMIDE 
• 67-56-1 methanol 
• 122-51-0 orthoformic acid triethyl ester 
• 149-73-5 trimethyl orthoformate 
• 119072-55-8 tert-butylisonitrile 
• 5455-59-4 2-Nitrobenzenesulfonamide 
• 72357-88-1 2-benzyl-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide 
• 13338-00-6 2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide 
• 62-53-3 aniline 

Downstream Products

• 37162-46-2 7-bromo-4H-1,2,4-benzothiadiazine 1,1-dioxide 
• 933024-24-9 4-(4-bromo-2-fluorobenzyl)-4H-1,2,4-benzothiadiazine 1,1-dioxide 
• 1256768-90-7 4-[4-(trifluoromethyl)benzyl]-4H-1,2,4-benzothiadiazine 1,1-dioxide 
• 896796-17-1 4-(3-nitrobenzyl)-4H-1,2,4-benzothiadiazine 1,1-dioxide 
• 1256768-91-8 4-(2,4,5-trifluorobenzyl)-4H-1,2,4-benzothiadiazine 1,1-dioxide 
• 359-84-2 3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxide 
• 2250-41-1 2--2H-1.2.4-benzothiadiazin-1.1-dioxid 
• 554-68-7 triethylamine hydrochloride 

Relevant academic research and scientific papers

Synthesis and in vitro antileishmanial efficacy of novel quinazolinone derivatives

Currently available drugs being used to treat leishmaniasis have several shortcomings, including high toxicity, drug administration that requires hospitalization, and the emergence of parasite resistance against clinically used drugs. As a result, there is a dire need for the development of new antileishmanial drugs that are safe, affordable, and efficient. In this study, two new series of synthesized quinazolinone derivatives were investigated as potential future antileishmanial agents, by assessing their activities against the Leishmania (L.) donovani and L.?major species. The cytotoxicity profiles of these derivatives were assessed in vitro on Vero cells. The compounds were found to be safer and without any toxic activities against mammalian cells, compared to the reference drug, halofuginone, a clinical derivative of febrifugine. However, they had demonstrated poor antileishmanial growth inhibition efficacies. The two compounds that had been found the most active were the mono quinazolinone 2d and the bisquinazolinone 5b with growth inhibitory efficacies of 35% and 29% for the L.?major and L.?donovani 9515 promastigotes, respectively. These outcomes had suggested structural redesign, inter alia the inclusion of polar groups on the quinazolinone ring, to potentially generate novel quinazolinone derivatives, endowed with effective antileishmanial potential.

Benzothiadiazine methoxy acrylate derivatives and preparation method and application thereof

The invention provides benzothiadiazine methoxy acrylate derivatives and a preparation method and application thereof, and the benzothiadiazine methoxy acrylate derivatives have the following chemicalstructural general formula VII as shown in the description, wherein R1 is hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy or nitro; and R2 is hydrogen, methyl or benzyl. According to the invention, an active group 3, 4-dihydro-2H-1, 2, 4-benzothiadiazine-1, 1-dioxo substitutes the side chain part of the methoxy acrylate bactericide and then is reasonably spliced with the pharmacophore of the methoxy acrylate bactericide, so that the bactericide with novel structure, broad spectrum, high efficiency and low toxicity is synthesized, the bactericide can be alternately used with the existing bactericide, the generation of resistance is avoided or delayed, the preparation conditions are conventional, the subsequent treatment is simple and convenient, and the industrialization is easy to realize.

Transition-metal and oxidant-free approach for the synthesis of diverse N-heterocycles by TMSCl activation of isocyanides

A highly efficient TMSCl-mediated addition of N-nucleophiles to isocyanides has been achieved. This transition-metal and oxidant-free strategy has been applied to the construction of various N-heterocyles such as quinazolinone, benzimidazole and benzothiazole derivatives by the use of distinct amino-based binucleophiles. The notable feature of this protocol includes its mild reaction condition, broad functional group tolerance and excellent yield. This journal is

Commercial Copper-Catalyzed Aerobic Oxidative Synthesis of Quinazolinones from 2-Aminobenzamide and Methanol

The focus of this study was the development of a new synthetic method for quinazolinones based on the principles of Green Chemistry. Quinazolinones were synthesized from 2-aminobenzamide using methanol as both the C1 source and a green solvent in the presence of base Cs2CO3. Additionally, a commercially available, economical copper complex was used as a catalyst in the reaction. The desired products were achieved in moderate to high yield with up to 99 % isolated yield.

Benzothiadiazine derivatives as well as preparation method and application thereof

The invention discloses benzothiadiazine derivatives as well as preparation methods and application thereof. The compounds have the structures of formula I or II. The invention also relates to preparation methods of the compounds containing the structures of formula I or II, pharmaceutical compositions and the application of the compounds in the preparation of anti-HBV drugs. The formula I or II are shown in the description.

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.

Acceptorless Dehydrogenative Coupling of o-Aminobenzamides with the Activation of Methanol as a C1 Source for the Construction of Quinazolinones

A strategy for the synthesis of quinazolinones via acceptorless coupling of o-aminobenzamides with methanol has been accomplished in the presence of the metal-ligand bifunctional catalyst [Cp?Ir(2,2′-bpyO)(H2O)]. Notably, this research exhibited the potential of transition-metal-catalyzed activation of methanol as a C1 source for the construction of heterocycles.

Acetic acid derivatives of 3,4-dihydro-2 H-1,2,4-benzothiadiazine 1,1-dioxide as a novel class of potent aldose reductase inhibitors

A series of novel benzothiadiazine 1,1-dioxide derivatives were synthesized and tested for their inhibitory activity against aldose reductase. Of these derivatives, 17 compounds, having a substituted N2-benzyl group and a N4-acetic acid group on the benzothiadiazine, were found to be potent and selective aldose reductase inhibitors in vitro with IC50 values ranging from 0.032 to 0.975 μM. 9m proved to be the most active in vitro. The eight top-scoring compounds coming from the in vitro test for ALR2 inhibition activity were then tested in vivo, whereby three derivatives, 9i, 9j, and 9m, demonstrated a significantly preventive effect on sorbitol accumulation in the sciatic nerve in the 5-day streptozotocin-induced diabetic rats in vivo. Structure-activity relationship and molecular docking studies highlighted the importance of substitution features of N4-acetic acid group and halogen-substituted N2-benzyl group in the benzothiadiazine scaffold and indicated that substitution with hallogen at C-7 had a remarkably strong effect on ALR2 inhibition potency.