Category: 73590-85-9

Application In Synthesis of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, is researched, Molecular C17H19N3O2S, CAS is 73590-85-9, about Whole-cell oxidation of omeprazole sulfide to enantiopure esomeprazole with Lysinibacillus sp. B71. Author is Babiak, Peter; Kyslikova, Eva; Stepanek, Vaclav; Valesova, Renata; Palyzova, Andrea; Maresova, Helena; Hajicek, Josef; Kyslik, Pavel.

Production of enantiopure esomeprazole by biocatalysis is of great demand by pharmaceutical industry. A Gram-pos. bacterium oxidizing omeprazole sulfide (5-methoxy-2-[((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)thio]-1H-benzoimidazole) to (S)-sulfoxide esomeprazole (S)-5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl) methylsulfinyl]-3H-benzoimidazole was isolated from soil polluted with elemental sulfur. The strain exhibited the highest identity with the genus Lysinibacillus and catalyzed oxidation of 1a into enantiopure esomeprazole with conversion of 77% in a stirred bioreactor, fed-batch culture. No consecutive oxidation of (S)-sulfoxide to sulfone was observed during whole-cell catalysis. The unique characteristics of the catalyst provide a solid basis for further improvement and development of sustainable green bioprocess.

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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole( cas:73590-85-9 ) is researched.Category: ethers-buliding-blocks.Amantea, Michael A.; Narang, Prem K. published the article 《Improved procedure for quantitation of omeprazole and metabolites using reversed-phase high-performance liquid chromatography》 about this compound( cas:73590-85-9 ) in Journal of Chromatography, Biomedical Applications. Keywords: omeprazole metabolite blood plasma HPLC; liquid chromatog omeprazole metabolite blood. Let’s learn more about this compound (cas:73590-85-9).

An HPLC procedure for the determination of omeprazole and its sulfone and sulfide metabolites in human plasma was developed by using a C8 reversed-phase column with a mobile phase of MeOH-MeCN-0.025M phosphate buffer (40:8:52) adjusted to pH 7.4 with 85% H3PO4 and detection at 302 nm. The level of detection was 5, 10, and 7.5 ng/mL for omeprazole, its sulfone, and the sulfide, resp. and the intraday variability ranged 2.6-10.3 and 2.0-3.5% at 10 and 125 ng/mL, resp. The recoveries were 96, 42, and 96% for omeprazole, the sulfone, and the sulfide, resp.

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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(SMILESS: CC1=CN=C(CSC2=NC3=CC(OC)=CC=C3N2)C(C)=C1OC,cas:73590-85-9) is researched.Product Details of 56621-48-8. The article 《A simple and sensitive bioanalytical assay for simultaneous determination of omeprazole and its three major metabolites in human blood plasma using RP-HPLC after a simple liquid-liquid extraction procedure. [Erratum to document cited in CA146:074538]》 in relation to this compound, is published in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences. Let’s take a look at the latest research on this compound (cas:73590-85-9).

On page 317, Table 2 is incorrect; in the first column titled “”Analyte””, the entries “”omeprazole sulfone”” and “”omeprazole”” should be reversed. On page 319, Table 3 is incorrect for the same reason Table 2 is incorrect. On pages 318 and 320, Figs. 3-5 are incorrect; each of the “”OPZ-SFN”” peaks should be labeled “”OPZ”” and the “”OPZ”” peaks should be labeled “”OPZ-SFN.””. On page 320, the legend of Figure 6 is incorrect; “”omeprazole sulfone”” should be replaced with “”omeprazole”” and “”omeprazole”” should be replaced with “”omeprazole sulfone.””.

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HPLC of Formula: 73590-85-9. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, is researched, Molecular C17H19N3O2S, CAS is 73590-85-9, about Mechanism of the asymmetric sulfoxidation in the esomeprazole process: effects of the imidazole backbone for the enantioselection. Author is Seenivasaperumal, Muthu; Federsel, Hans-Jurgen; Szabo, Kalman J..

The asym. sulfoxidation reaction of imidazole-based prochiral sulfides was studied to explore the mechanistic details of the highly efficient esomeprazole process, which is one of the few industrial scale catalytic asym. procedures. The synthetic studies revealed that the smallest subunit governing the selectivity in the esomeprazole process is an imidazole ring. Thus, by using the esomeprazole procedure Me imidazole sulfide could be oxidized as efficiently as its several functionalized derivatives, including pyrmetazol. However, alkylation of the imidazole nitrogen led to a major drop of the enantioselectivity. Our atm. pressure chem. ionization-mass spectrometry (APCI/MS) studies indicate that addition of small amounts of water to the reaction mixture facilitates the formation of mononuclear titanium species, which are the active catalytic intermediates of the selective oxidation reaction. One of the most important features of the esomeprazole procedure is that amine additives increase the enantioselectivity of the oxidation process. The NMR studies of the presumed reaction intermediates show that under catalytic conditions the amines are able to coordinate to titanium and dissociate the coordinated imidazole substrate. The d. functional theory (DFT) modeling studies provided new insights in the mechanism of the asym. induction. It was found that the oxidation requires a lower activation energy if the imidazole sulfide precursor does not coordinate to titanium. Two possible reaction paths were explored for this out of sphere oxidation mechanism. The most important interaction governing the enantioselection is hydrogen bonding between the N-H of the imidazole ring and the chiral tartrate ligand on titanium. Furthermore, the oxidation reaction imposes an important structural constraint to the TS structure involving a linear arrangement of the peroxide oxygens and the sulfur atom. This constraint and the N coordination of imidazole leads to a very strained structure for the inner sphere mechanism of the oxidation, which leads to a much higher activation barrier than the corresponding out of sphere process, and therefore it is unlikely.

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Ether – Wikipedia,
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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(SMILESS: CC1=CN=C(CSC2=NC3=CC(OC)=CC=C3N2)C(C)=C1OC,cas:73590-85-9) is researched.Reference of 1-Methyl-3-(thiophen-2-yl)-1H-pyrazol-5-amine. The article 《Development and validation of a precise single HPLC method for determination of omeprazole and its related compound in pharmaceutical formulation》 in relation to this compound, is published in International Journal of ChemTech Research. Let’s take a look at the latest research on this compound (cas:73590-85-9).

A simple reversed-phase high performance liquid chromatog. was developed and employed for the determination of omeprazole and its related substances in bulk material and com. dosage forms. A gradient elution of filtered sample was performed on Zorbax XDB C8 (150 × 4.6), 5μ column with Glacine buffer (pH-8.8) as a mobile phase-A, Acetonitrile : Methanol (83:17) as a mobile phase-B and UV detection at 302 nm. Mobile phase was delivered at flow of 1.2 mL/min and at maintaining the column temperature at 25°C, quantification was achieved with reference to the external standards The active ingredient – omeprazole was successfully separated from its all related substances, including process impurities and other possible impurities of oxidation and decomposition The excipients did not interfere with the determination of omeprazole and its related compound in com. dosage formulations. The method was rapid, simple, accurate and reproducible. It was not only successfully employed for the assay of omeprazole in bulk material and pharmaceutical dosage forms but also for the determination of its related substances. A statistical design of experiments was used for the robustness evaluation of HPLC anal. method. All results were acceptable and confirmed that the method is suitable for its intended use.

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Electric Literature of C17H19N3O2S. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, is researched, Molecular C17H19N3O2S, CAS is 73590-85-9, about Determination of the dissociation constants of omeprazole and its intermediate by capillary electrophoresis. Author is Podobnik, B.; Jelen-Zmitek, A..

Capillary electrophoresis is the primary method for determining dissociation constants of compounds which have low solubility in H2O, which is often the case for pharmaceuticals. Potentiometric determination in these cases is difficult because of lowered sensitivity. A new method is based on measurement of ionic mobility as a function of the pH of the buffer used.

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Ether – Wikipedia,
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Related Products of 73590-85-9. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, is researched, Molecular C17H19N3O2S, CAS is 73590-85-9, about Development of a validated RP-HPLC method for separation and determination of process-related impurities of omeprazole in bulk drugs. Author is Iuga, Cristina; Bojita, Marius; Leucuta, Sorin E..

A gradient reversed phase liquid chromatog. (RP-LC) method was developed and subsequently validated for the determination of omeprazole and its process-related impurities (noted as: impurity A, B, C, D, G, H). Separation was achieved with a Zorbax Extend C18 column and acetonitrile: water: triethylaminel percent (pH adjusted to 9.5) as eluent, at a flow rate of 0.8 mL/min. UV detection was performed at 280 nm. The described method was linear over a range of 40.6-203 μg/mL for omeprazole, 0.9556-14.334 μg/mL for impurity A, 1.1568-17.352 μg/mL for impurity B, 1.0772-16.158 μg/mL for impurity C, 1.289-19.344 μg/mL for impurity D, and 0.7968-11.952 μg/mL for impurity H. The accuracy of the method was demonstrated at 5 concentration levels in the range of 60-140% of the specification limit and the recovery of impurities was found to be in the range of 90-109%. The method is simple, rapid, selective, accurate, and useful for indicating the stability of omeprazole from dosage forms. The method can be useful in the quality control of bulk manufacturing and pharmaceutical formulations.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Validation of an automated liquid chromatographic method for omeprazole in human plasma using on-line solid-phase extraction.》. Authors are García-Encina, G; Farrán, R; Puig, S; Martínez, L.The article about the compound:5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazolecas:73590-85-9,SMILESS:CC1=CN=C(CSC2=NC3=CC(OC)=CC=C3N2)C(C)=C1OC).Safety of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole. Through the article, more information about this compound (cas:73590-85-9) is conveyed.

An automated system using on-line solid-phase extraction and HPLC with UV detection has been validated in order to determine omeprazole in human plasma. The extraction was carried out using C18 cartridges. After washing, omeprazole was eluted from the cartridge with mobile phase onto an Inertsil ODS-2 column. The developed method was selective and linear for drug concentrations ranging between 5 and 500 ng ml(-1). The recovery of omeprazole ranged from 88.1 to 101.5%, and the limit of quantitation (LOQ) was 5 ng ml(-1). The intraday accuracy ranged from 93.1 to 106.2% and the interday accuracy varied from 95.4 to 105.1%. For the LOQ, good values of precision (8.7 and 17.5% for intraday and interday, respectively) were also obtained. This automated system has been applied to determine omeprazole in human plasma samples from bioequivalence studies.

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Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, is researched, Molecular C17H19N3O2S, CAS is 73590-85-9, about Effect of hypoxia on oxidative and reductive pathways of omeprazole metabolism by the isolated perfused rat liver.Recommanded Product: 73590-85-9.

The effect of hypoxia on the elimination of H168-68 (omeprazole)(I) [73590-58-6] a potent inhibitor of gastric acid secretion, was studied in the isolated perfused rat liver. During normal oxygenation, a 10 mg bolus dose was eliminated rapidly (half-life (T1/2)-β = 8.0 min), while under hypoxic conditions T1/2β was increased to 81.6 min. Upon reoxygenation, T1/2β returned to 9.6 min. During hypoxia, perfusate concentrations of an oxidative metabolite (I-sulfone [88546-55-8]) were reduced by 68%, while those of the reductively-generated I-sulfide [73590-85-9] increased 4-fold. With reoxygenation, both formation and elimination of the sulfone were increased, whereas, which had accumulated during the hypoxic period, was eliminated rapidly. These findings were duplicated in steady-state experiments, in which omeprazole clearance during hypoxia fell by at least 70%, and sulfide concentrations in perfusate rose from undetectable levels to 200 ng/mL (at least a 10-fold increase). Sulfone concentrations did not change with hypoxia, consistent with a reduction in both its formation and elimination rates. Thus, the hepatic elimination of omeprazole is severely retarded by hypoxia, but this effect is promptly reversed by reoxygenation. The increased formation of the reductive metabolite during hypoxia is not of sufficient magnitude to sustain the normal hepatic elimination of omeprazole.

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Lindberg, Per; Nordberg, Peter; Alminger, Tomas; Braendstroem, Arne; Wallmark, Bjoern published an article about the compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole( cas:73590-85-9,SMILESS:CC1=CN=C(CSC2=NC3=CC(OC)=CC=C3N2)C(C)=C1OC ).Recommanded Product: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:73590-85-9) through the article.

The very potent gastric antisecretory agent omeprazole (I) [73590-58-6], presently under clin. evaluation, has been shown to act via inhibition of the gastric H+, K+-ATPase, the enzyme responsible for pumping of protons into the stomach. I needs acid activation to become an active inhibitor. A tetracyclic sulfenamide (II) was isolated from the acid decomposition of I. This sulfenamide, or, alternatively, the corresponding sulfenic acid, an unstable, probable intermediate in the sulfenamide formation, is the active inhibitor formed in vivo from omeprazole.

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