5510-09-8

Upstream product

• 35511-14-9 methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide 
• 40506-05-6 1,1-dioxo-2-(2-oxo-propyl)-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one 
• 128-44-9 saccharin sodium salt 
• 76508-40-2 (1,1,3-Trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-acetic acid phenyl ester 
• 76508-37-7 (1,1,3-Trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-acetic acid isopropyl ester 
• 76524-15-7 2-(Isopropoxycarbonylmethyl-sulfamoyl)-benzoic acid isopropyl ester 
• 76508-34-4 2-(Ethoxycarbonylmethyl-sulfamoyl)-benzoic acid ethyl ester 
• 76508-33-3 methyl 2- benzoate 
• 76508-35-5 isopropyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide 
• 24683-20-3 ethyl 2-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl) acetate 
• 6639-62-9 methyl 3-oxo-2,3-dihydrobenzo[d][1,2]thiazol-2-acetate 1,1-dioxide 
• 66366-27-6 (1,1,3-trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-acetic acid tert-butyl ester 
• 81-07-2 saccharin 
• 24683-21-4 4-hydroxy-2H-1,2-benzothiazine-3-carboxylic acid ethyl ester 1,1-dioxide 

Relevant academic research and scientific papers

Hybrid compounds from chalcone and 1,2-benzothiazine pharmacophores as selective inhibitors of alkaline phosphatase isozymes

Chalcones and 1,2-benzothiazines are two important classes of bioactive compounds, each scaffold endowed with diverse pharmacological activities. Combining both of these pharmacophores in a single molecule was aimed to yield multi-modal agents. Herein, we report a series of hybrid compounds 3a–3o derived from chalcones and 1,2-benzothiazine cores. They were synthesized from commercially available sodium saccharin, and the resulting 1,2-benzothiazine-derived ketone was then condensed with aromatic aldehydes in an aldol condensation to obtain the respective chalcones. The compounds were characterized using different analytical techniques including FT-IR, NMR spectroscopy, mass spectrometry and X-ray crystallography. Some synthesized chalcones revealed potent and/or selective inhibitory properties towards alkaline phosphatase isozymes transiently expressed in COS-7 cells. A detailed structure-activity and selectivity study was carried out with regard to the effect of different substituents at ortho-, meta- and para-positions of the phenyl residue. Compound 3c was the most effective human intestinal alkaline phosphatase (h-IAP) inhibitor (IC50 value of 1.04 μM), while it was not active against human tissue non-specific alkaline phosphatase (h-TNAP) isozyme. In contrast, 3i was a selective inhibitor of h-TNAP with IC50 values of 0.25 ± 0.01 μM. The possible binding interactions of the most effective inhibitors of h-TNAP and h-IAP were obtained from molecular docking studies.

Stereopure Functionalized Benzosultams via Ruthenium(II)-Catalyzed Dynamic Kinetic Resolution-Asymmetric Transfer Hydrogenation

A highly diastereo- and enantioselective Ru(II)-catalyzed dynamic kinetic resolution-asymmetric transfer hydrogenation (DKR-ATH) of α-(N-sulfonylimino) and α-(N-sulfonylamino) aryl ketones to 4-hydroxy-benzo-δ- and 3-(α-hydroxy-arylmethyl)-benzo-γ-sultams is presented. By employing enantiopure ansa-Ru[PipSO2DPEN(CH2)4Ph] cat. II with S/C = 10 000 in a HCO2H/Et3N binary mix, up to >99.9% ee and dr >99:1 are obtained with 100% conversion under mild conditions. Application to access the stereopure "structurally simplified TsDPEN" N,N-ligand syn-3-(α-aminobenzyl)-benzo-γ-sultam ("syn-ULTAM") and its structural isomer trans-4-amino-3-phenyl-benzo-δ-sultam (trans-4) is demonstrated.

Discovery of (2-benzoylethen-1-ol)-containing 1,2-benzothiazine derivatives as novel 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibiting-based herbicide lead compounds

A series of (2-benzoylethen-1-ol)-containing benzothiazine derivatives was synthesized, and their herbicidal activities were first evaluated. The bioassay results indicated that some of 3-benzoyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-1,1-dioxide derivatives displayed good herbicidal activity in greenhouse testing, especially, compound 4w had good pre-emergent herbicidal activities against Brassica campestris, Amaranthus retroflexus and Echinochloa crusgalli even at a dosage of 187.5 g ha-1. More importantly, compound 4w displayed significant inhibitory activity against Arabidopsis thaliana HPPD and was identified as the most potent candidate with IC50 value of 0.48 μM, which is better than the commercial herbicide sulctrione (IC50 = 0.53 μM) and comparable with the commercial herbicide mesotrione (IC50 = 0.25 μM). The structure-activity relationships was studied and provided some useful information for improving herbicidal activity. The present work indicated that (2-benzoylethen-1-ol)-containing 1,2-benzothiazine motif could be a potential lead structure for further development of novel HPPD inhibiting-based herbicides.

4-hydroxy-3-benzoyl-2-alkyl -1,2-benzothiazine -1,1-dioxide derivatives of the (by machine translation)

The invention relates to a 4-hydroxy-3-benzoyl-2-alkyl -1,2-benzothiazine -1,1-dioxide derivatives, structural formula as (I). wherein: R 1 representative: C1-C5 alkyl; R 2 representative: 2-NO 2, 3-NO 2, 4-NO 2, 2-Br-4-Br, 2-Cl-3-Cl, 2-Cl-5-Cl, 2-Cl-4-F, 2-Cl-4-Br, 2-F-4-Cl, 2-Br-4-F, 2-Br-4-Cl, 2-Cl-4-NO 2, 2-Cl-4-CF 3, 4-SO 2 Me. To saccharines sodium salt as raw materials, by nucleophilic reaction, rearrangement Gabriel-Colman, decarboxylative, alkylation, condensation and Fries rearrangement reaction, the obtained 4-hydroxy-3-benzoyl-2-alkyl -1,2-benzothiazine -1,1-dioxide compound, and the herbicidal activity of the compound to the test, the results show that the compound has a good herbicidal activity, is a novel structure, application prospect of herbicides. (by machine translation)

NRF2 REGULATORS

The present invention relates to bis aryl analogs, pharmaceutical compositions containing them and their use as Nrf2 regulators.

1,2-Benzothiazine 1,1-dioxide carboxylate derivatives as novel potent inhibitors of aldose reductase

Due to the importance of aldose reductase (ALR2) as a potential drug target in the treatment of diabetic complications, there are increasing interests in design and synthesis of ALR2 inhibitors. Here, we prepared 1,2-benzothiazine 1,1-dioxide acetic acid derivatives and investigated their inhibition activity. Most of these derivatives were found to be active with IC50 values ranging from 0.11 μM to 10.42 μM, and compound 8d, 2-[2-(4-bromo-2- fluorobenzyl)-1,1-dioxido-2H-1,2-benzothiazin-4(3H)-ylidene]acetic acid, showed the most potent inhibition activity. Further, SAR and docking studies suggest that in comparison with the α,β-unsaturated derivatives, the saturated carboxylic acid derivatives had a greater binding affinity with the enzyme and thus an enhanced inhibition activity. Therefore, development of more powerful ARIs based on benzothiazine 1,1-dioxide by stereo-controlled synthesis could be expected.

Synthesis and in vitro evaluation of novel small molecule inhibitors of bacterial arylamine N-acetyltransferases (NATs)

The synthesis and inhibitory activity of a series of 5-substituted-(1,1-dioxo-2,3-dihydro-1H-1λ6-benzo[e] [1,2]thiazin-4-ylidene)-thiazolidine-2,4-dione derivatives as competitive inhibitors of recombinant bacterial arylamine-N-acetyltransferas

3-Oxo-1,2-benzoisothiazoline-2-acetic Acid 1,1-Dioxide Derivatives. I. Reaction of Esters with Alkoxides

Reaction of 3-oxo-1,2-benzoisothiazoline-2-acetic acid alkyl esters 1,1-dioxide (1a-d) with alkaline alkoxides was carried out under various conditions.Under mild conditions, o-(N-carboxymethylsulfamyl)benzoic acids dialkyl esters (2a-d) were obtained with good yields.Reaction of 1a-d or 2a-d with sodium alkoxide under drastic conditions afforded 4-hydroxy-2H-1,2-benzothiazine-3-carboxylic acid alkyl esters 1,1-dioxide (3a-d).Transesterification was observed when esters 1b-d were treated with sodium methoxide in methanol.Esters 3a-d were hydrolyzed in concentrated aqueous sodium hydroxide affording the acid 6.Attempts to recrystallize 6 from water resulted in its decarboxylation to give 2H-1,2-benzothiazine-4-(3H)one 1,1-dioxide (7).Compound 6 could not be obtained by acid hydrolysis of esters 3a-d or by rearrangement of 3-oxo-1,2-benzoisothiazoline-2-acetic acid 1,1-dioxide (8).Different experimental evidence supports the suggestion that rearrangement took place by ethanolysis of the carboxamide linkage affording the open sulfonamides (fast step) followed by a Dieckmann cyclization (slow step).It was demonstrated that transesterification took place in the open sulfonamides 2.