24683-20-3

Usage

Uses

Piroxicam impurity E.

InChI:InChI=1/C11H11NO5S/c1-2-17-10(13)7-12-11(14)8-5-3-4-6-9(8)18(12,15)16/h3-6H,2,7H2,1H3

Upstream product

• 105-39-5 chloroacetic acid ethyl ester 
• 81-07-2 saccharin 
• 118463-44-8 2-ethoxycarbonylmethyl-3-hydrazino-1,2-benzisothiazole-1,1-dioxide 
• 118463-46-0 [3-(Isopropylidene-hydrazono)-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl]-acetic acid ethyl ester 
• 128-44-9 saccharin sodium salt 
• 105-36-2 ethyl bromoacetate 
• 685-87-0 Diethyl 2-bromomalonate 
• 4299-16-5 (1,2-Benzisothiazolin-3-on-2-yl)essigsaeureethylester 
• 141-78-6 ethyl acetate 

Downstream Products

• 52188-11-1 2-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)acetic acid 
• 220223-03-0 N-(2-carboxyphenylsulfonyl)glycine 
• 35511-14-9 methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide 
• 76508-34-4 2-(Ethoxycarbonylmethyl-sulfamoyl)-benzoic acid ethyl ester 
• 128328-86-9 3,3-Bis-benzylsulfanyl-2-(1,1,3-trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-acrylic acid ethyl ester 
• 113412-08-1 2-(Ethoxycarbonylmethyl-methyl-sulfamoyl)-benzoic acid ethyl ester 
• 24683-26-9 ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide 
• 35511-63-8 N-(4'-chlorophenyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide 
• 35511-66-1 4-hydroxy-2-methyl-N-[3-(trifluoromethyl)phenyl]-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide 
• 34258-79-2 4-hydroxy-2-methyl-N-phenyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide 
• 35510-91-9 4-hydroxy-2-methyl-N-[4-(trifluoromethyl)phenyl]-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide 
• 5510-09-8 1,1-dioxo-2,3-dihydro-1H-1λ⁶-benzo[e][1,2]thiazin-4-one 
• 24683-22-5 4-hydroxy-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide 
• 20566-30-7 2-ethoxycarbonylmethyl-1,1,4-trioxo-1,2,3,4-tetrahydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Site-specific acid-base properties of tenoxicam

The Hammett approach, as a new deductive tool, was introduced to characterize the otherwise inaccessible minor protonation pathway of tenoxicam (1), the non-steroidal anti-inflammatory drug. A total of eight compounds, constituting a systematic series of side chain-substituted analogues of tenoxicam and piroxicam (2), were synthesized and studied in terms of acid-base properties and Hammett constants to identify the ideal replacement of the unprotonated pyridin-2-yl group, a key moiety in both molecules. Hammett constants of the phenyl substituents have been found to be in a linear correlation with the experimental log K values of the enolate sites, the basic moiety of the extended conjugated system in this family of piroxicam derivatives. Then, a similar correlation was observed for the analogous tenoxicam derivatives. After identifying the 2-aza Hammett constant of the pyridin-2-yl group and the corresponding log K value, the site-specific acid-base properties of tenoxicam could be quantitated. This novel method is assessed to be a fine-tuning tool to find the ideal substituent by using analogue-based deductive method to obtain site-specific constants of the minor protonation/deprotonation pathway in drugs and biomolecules. The tenoxicam microconstant values indicate that the enolate moiety is of extremely low basicity (reflected by the log kO = 3.70 and log kO N = 1.09 values), which can, however, be interpreted in terms of the peculiar ring system and the overwhelming electron-withdrawing effects of the adjacent heteroatoms. A diagram depicting the pH-dependent distribution of 1 microspecies is also presented.

Synthesis and biological evaluation of Piroxicam derivative as a lead chelator

Lead as a potent environmental and occupational pollutant, exerts its toxic effect mainly through oxidative stress induction. Currently, chelation therapy is the only medical management of metal intoxications in clinic, but its administration is associated with various side effects as well. In this study the protective effect of synthetized Piroxicam derivative was evaluated against lead toxicity in vitro. First the chelating activity of Piroxicam derivative was studied through Jobs method and 13C{1H} NMR spectroscopy. Then the cytoprotective effect of Piroxicam derivative (10, 20, 50, 100 and 200 μg/mL) was evaluated and compared with that of EDTA (30 μg/mL) in the presence of lead nitrate (30 μg/mL). The EC50 value of Piroxicam derivative was calculated as well. Finally, the chelation efficacy and antioxidant effects of Piroxicam derivative in EC50 and 2EC50 values was assessed and compared with that of EDTA. Results showed that Piroxicam derivative chelates lead ion as much as EDTA. Moreover, Piroxicam derivative prevented lead-induced cells death more effectively than EDTA which is may due to its potent innate antioxidant activity. In conclusion, the synthetized Piroxicam derivative with possessing potent chelating activity as well as potent antioxidant activity, could be considered as potential drug target in management of toxic metals poisoning.

Piroxicam Analogs: Design, Synthesis, Docking Study and Biological Evaluation as Promising Anti-HIV-1 Agents

Objective: In this study, we describe the synthesis, docking study and biological evaluation of 1,2-benzothiazines 1,1-dioxide derivatives. Methods: Taking the well-known drug, Piroxicam as a lead compound, we designed and synthesized two series of 1,2-be

5-aminothiazole non-steroidal anti-inflammatory compound as well as preparation method and application thereof

The invention discloses a 5-aminothiazole non-steroidal anti-inflammatory compound. The compound which is efficient, low in toxicity and small in side effect is prepared from an ester intermediate containing a thiazine ring and a 5-aminothiazole derivative through a transesterification reaction. The preparation method of the compound is simple, the compound has the active groups of the existing non-steroidal anti-inflammatory medicine; meanwhile, the special change of the nitrogen atom position is also designed; compared with the existing non-steroidal anti-inflammatory medicines, the compoundhas better anti-inflammatory and analgesic effects, particularly has good curative effects on arthritis, osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, soft tissue inflammation and thelike, has small toxic and side effects on human bodies, and has a very wide market prospect.

Piroxicam hapten and preparation method and application thereof

The invention aims to provide a piroxicam hapten and a synthesis method and application thereof, belonging to the field of drug safety detection. The preparation method comprises the following steps:1) mixing saccharin and ethyl bromoacetate for reacting to prepare an intermediate product 1; 2) mixing and extracting the intermediate product 1 with DMSO and MeONa to obtain an intermediate product2; 3) mixing the intermediate product 2 and CH3I for reacting to obtain an intermediate product 3; 4) mixing the intermediate product 3 and 6-aminonicotinic acid methyl ester for reacting to obtain anintermediate product 4; 5) after adding of the intermediate product 4 into a reagent for miscibility reaction, purifying to obtain the final product, namely the piroxicam hapten. Immunological detection method has the advantages of high sensitivity, strong specificity, simple sample pretreatment, short detection time, strong stability, no need of special equipment and reagents, intuitive judgmentof results and the like, thus being particularly suitable for rapid detection of illegal addition of piroxicam chemical drugs in vast basic inspection personnel and large quantities of anti-rheumatism Chinese patent medicines.

Synthetic method of piroxicam drug intermediate 3-oxo-1,2-benzisothiazole-1,1-dioxo-2-ethyl acetate

A synthetic method of a piroxicam drug intermediate 3-oxo-1,2-benzisothiazole-1,1-dioxo-2-ethyl acetate comprises the following steps: adding 2.16mol of saccharin amine and 2.1-2.3L of nitromethane into a reaction container provided with a stirrer, a reflux condenser, a dropping funnel and a thermometer, controlling a stirring speed to be 160-190rpm, rising the temperature of a solution to 110-115 DEG C, slowly adding 2.3-2.5mol of ethyl acetate, after adding continuously stirring for 11-13h, distilling off most of the nitromethane, pouring a reactant into a potassium chloride solution, performing suction filtration to obtain a white solid, recrystallizing by using 900ml of propionitrile, reducing the temperature of a solution to 3-5 DEG C, standing for 30-36h, performing suction filtration, washing by using methylbenzene, and dehydrating by a dehydrating agent, thus obtaining the 3-oxo-1,2-benzisothiazole-1,1-dioxo-2-ethyl acetate, wherein the mass fraction of the potassium chloride solution is 15-20 percent, and the mass fraction of the propionitrile is 80-85 percent.

Design, synthesis and evaluation of N-substituted saccharin derivatives as selective inhibitors of tumor-associated carbonic anhydrase XII

A series of N-alkylated saccharin derivatives were synthesized and tested for the inhibition of four different isoforms of human carbonic anhydrase (CA, EC 4. 2.1.1): the transmembrane tumor-associated CA IX and XII, and the cytosolic CA I and II. Most of the reported derivatives inhibited CA XII in the nanomolar/low micromolar range, hCA IX with KIs ranging between 11 and 390 nM, whereas they were inactive against both CA I (KIs >50 μM) and II (KIs ranging between 39.1 nM and 50 μM). Since CA I and II are off-targets of antitumor carbonic anhydrase inhibitors (CAIs), the obtained results represent an encouraging achievement for the development of new anticancer candidates without the common side effects of non-selective CAIs. Moreover, the lack of an explicit zinc binding function on these inhibitors opens the way towards the exploration of novel mechanisms of inhibition that could explain the high selectivity of these compounds for the inhibition of the transmembrane, tumor-associated isoforms over the cytosolic ones.

Design, synthesis and preliminary bioactivity studies of 1,2-dihydrobenzo[d]isothiazol-3-one-1,1-dioxide hydroxamic acid derivatives as novel histone deacetylase inhibitors

Histone deacetylase (HDAC) is a clinically validated target for antitumor therapy. In order to increase HDAC inhibition and efficiency, we developed a novel series of saccharin hydroxamic acids as potent HDAC inhibitors. Among them, compounds 11e, 11m, 11

DERIVATIVES OF 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOLS AS PHOSPHODIESTERASE INHIBITORS

Compounds, pyridine N-oxides, and pharmaceutically acceptable salts of formula (I) are useful as inhibitors of the phosphodiesterase 4 (PDE4) enzyme and for preventing and/ or treating diseases of the respiratory tract characterized by airway obstruction, such as asthma or COPD.

DERIVATIVES OF 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOLS AS PHOSPHODIESTERASE INHIBITORS

The invention relates to inhibitors of the phosphodiesterase 4 (PDE4) enzyme. More particularly, the invention relates to compounds that are derivatives of 1-phenyl-2-pyridinyl alkyl alcohols, methods of preparing such compounds, compositions containing them and therapeutic use thereof.