Category: 73590-85-9

Zhou, Guobin; Guan, Yueqing published an article in 2016, the title of the article was An efficient asymmetric approach to the R-enantiomer impurity of esomeprazole.Recommanded Product: 73590-85-9 And the article contains the following content:

The R-enantiomer of esomeprazole (5-methoxy-2-[(4-methoxy-3, 5-dimethyl-2-pyridinylmethyl)sulfinyl]-1H-benzimidazole) was synthesized with high enantioselectivity by asym. oxidation of prochiral sulfide using the oxaziridinium salt. This (R)-enantiomer, useful as a reference for the quality control of esomeprazole was characterized by 1H and 13CNMR, IR and HRMS. The enantiomeric excess was determined by HPLC. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Recommanded Product: 73590-85-9

The Article related to esomeprazole preparation enantioselective, Heterocyclic Compounds (More Than One Hetero Atom): Oxazoles, Isoxazoles and other aspects.Recommanded Product: 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On July 15, 2022, Xu, Qingzhu; Xiao, Xinrui; Zhou, Rui; Zhang, Xu; Yu, Lei published an article.Related Products of 73590-85-9 The title of the article was Concise selenization of polystyrene via the FeCl3-catalyzed reaction with (PhSe)2. And the article contained the following:

Selenization of polystyrene is a key process for preparing the selenium-containing functional materials with industrial application potential. However, traditional methods suffer from tedious reaction steps and the use of inflammable or hazardous reagents. Herein, we report a novel method for polystyrene selenization just by immersing the material in (PhSe)2/FeCl3 solution under mild conditions. This is the first report on the selenization of materials using PhSe+ cation via the electrophilic substitution strategy. The selenized styrene was catalytically active for the oxidation of Ufiprazole to Omeprazole, an important reaction in pharmaceutical industry. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Related Products of 73590-85-9

The Article related to selenization polystyrene iron trichloride catalyst, Chemistry of Synthetic High Polymers: Chemical Transformation Of Polymers and other aspects.Related Products of 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Babiak, Peter; Kyslikova, Eva; Stepanek, Vaclav; Valesova, Renata; Palyzova, Andrea; Maresova, Helena; Hajicek, Josef; Kyslik, Pavel published an article in 2011, the title of the article was Whole-cell oxidation of omeprazole sulfide to enantiopure esomeprazole with Lysinibacillus sp. B71.SDS of cas: 73590-85-9 And the article contains the following content:

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. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).SDS of cas: 73590-85-9

The Article related to lysinibacillus omeprazole sulfide oxidation enantiomer, Fermentation and Bioindustrial Chemistry: Pharmaceuticals (Including Nutrients) and other aspects.SDS of cas: 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On October 31, 2021, Zhang, Yuanyuan; Lv, Kuiying; Deng, Yashan; Li, Huiling; Wang, Zhiyong; Li, Depeng; Gao, Xin; Wang, Fanye published an article.Formula: C17H19N3O2S The title of the article was Asymmetric Bio-oxidation Using Resting Cells of Rhodococcus rhodochrous ATCC 4276 Mutant QZ-3 for Preparation of (S)-Omeprazole in a Chloroform-Water Biphasic System Using Response Surface Methodology. And the article contained the following:

Abstract: (S)-Omeprazole is a very effective anti-ulcer medicine that is difficult to be prepared using whole cells at elevated substrate concentrations In the chloroform-water biphasic system, resting cells of the mutant QZ-3 of Rhodococcus rhodochrous (R. rhodochrous) ATCC 4276 were used to catalyze the bio-oxidation of omeprazole sulfide for preparation of (S)-omeprazole. Using response surface methodol. (RSM), the reaction was optimized to work at a substrate concentration of 180 mM and a cell concentration of 100 g/L. The optimal yield of (S)-omeprazole obtained was 92.9% with enantiomeric excess (ee) (> 99%), and no sulfone byproduct was detected under the optimal working conditions; reaction temperature 37°C, pH 7.3 and reaction time, 43 h. A quadratic polynomial model was established, which predicts the exptl. data with very high accuracy (R2 = 0.9990). The chloroform-water biphasic system may contribute to the significant improvement in substrate tolerance because almost all substrates are partitioned in the organic phase (water solubility of omeprazole sulfide is only about 0.5 mg/mL), resulting in little damage and inhibition to cells by substrates. The mutant QZ-3 of R. rhodochrous ATCC 4276 exhibited high enantioselectivity, activity and substrate and product tolerance. The aerated flask provides enough oxygen for a high concentration of cells. Accordingly, bio-oxidation is thus more promising for efficient preparation of chiral sulfoxides. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Formula: C17H19N3O2S

The Article related to rhodococcus s omeprazole chloroform water biphasic system, Fermentation and Bioindustrial Chemistry: Pharmaceuticals (Including Nutrients) and other aspects.Formula: C17H19N3O2S

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On March 31, 2022, Tang, Hui; Zhang, Yuanyuan; Deng, Yashan; Du, Shanshan; Li, Depeng; Wang, Zhiyong; Li, Huiling; Gao, Xin; Wang, Fanye published an article.Recommanded Product: 73590-85-9 The title of the article was Optimization of Synthesis of (S)-Omeprazole Catalyzed by Soybean Pod Peroxidase in Water-in-Oil Microemulsions Using RSM. And the article contained the following:

Response surface methodol. (RSM) was used to optimize the oxidizing the omeprazole sulfide to (S)-omeprazole catalyzed by environmentally friendly catalyst soybean pod peroxidase (SPP) in cetyltrimethylammonium bromide (CTAB)/isooctane/n-Bu alc./water water-in-oil microemulsions. With the initial concentration of SPP of 3200 U ml-1, the conversion of the omeprazole sulfide, the (S)-omeprazole yield and ee were 93.75%, 91.56% and 96.08%, resp., under the optimal conditions: Wo of 15.85, the concentration of H2O2 of 22.44 mM and reaction temperature of 49.68°C, resp. The proposed mechanism of asym. sulfoxidations catalyzed by SPP involves three concomitant mechanisms as follows: (1) a two-electron reduction of SPP-I, (2) a single-electron transfer to SPP-I and (3) nonenzymic reactions. Based on the proposed mechanism which is reasonable and can express the oxidations, the reaction system includes five enzymic and two nonenzymic reactions. With 5.44% of the average relative error, a kinetic model based on the mechanisms fitting observed data very well was established, and the SPP-catalyzed reactions including both the two-electron reduction and the single-electron transfer mechanisms obey ping-pong mechanism with substrate and product inhibition, while nonenzymic reactions follow a power law. This study has also demonstrated the feasibility of SPP as a substitute with low cost, excellent enantioselectivity and better thermal stability. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Recommanded Product: 73590-85-9

The Article related to soybean peroxidase water in oil microemulsion omeprazole optimization rsm, Fermentation and Bioindustrial Chemistry: Pharmaceuticals (Including Nutrients) and other aspects.Recommanded Product: 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On April 1, 2019, Zhang, Yan; Wu, Yin-Qi; Xu, Na; Zhao, Qian; Yu, Hui-Lei; Xu, Jian-He published an article.Category: imidazoles-derivatives The title of the article was Engineering of cyclohexanone monooxygenase for the enantioselective synthesis of (S)-omeprazole. And the article contained the following:

Enzymic asym. sulfoxidation using mol. oxygen as the oxidant is a promising green chem. approach to chiral sulfoxide production Despite the broad substrate spectrum of cyclohexanone monooxygenases (CHMOs), some unnatural substrates with bulky functional groups, such as the pharmaceutically relevant omeprazole sulfide, cannot be effectively accepted by CHMOs. Herein, we describe a set of variants derived from an Acinetobacter calcoaceticus CHMO (AcCHMO), whose active sites adjacent to the substrate tunnel were altered to shift the substrate specificity from cyclohexanone monooxygenation toward omeprazole sulfide sulfoxidation We performed homologous modeling and mol. docking to identify key residues that might affect the substrate specificity. Two libraries of residues lining the active center of AcCHMO were then constructed and screened by an effective halo-based selection method using the solubility difference between the substrate (omeprazole sulfide) and product (esomeprazole). Functional evaluation of the resultant variants showed that the substrate specificity of AcCHMO was markedly altered from the small natural substrate (cyclohexanone) toward the desired bulky substrate (omeprazole sulfide) despite the extremely poor activity detected even for the best variant, M2 (0.61 U/gprot). The crystal structure of M2 complexed with a FAD prosthetic group was determined, which provided insight into the altered substrate specificity. To improve the activity of enzyme M2 toward pharmaceutical precursor omeprazole sulfide, we performed both local and global protein engineering among the two CASTing libraries surrounding FAD+ and NADP+ prosthetic groups and an error-prone PCR library of the full-length AcCHMO. As a result, variant M6 was obtained, giving a 50-fold higher activity compared to M2. This structure-guided protein engineering of AcCHMO provided a promising candidate for converting omeprazole sulfide into (S)-omeprazole using a green biocatalytic method. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Category: imidazoles-derivatives

The Article related to cyclohexanone monooxygenase engineering enantioselective synthesis s omeprazole, Fermentation and Bioindustrial Chemistry: Pharmaceuticals (Including Nutrients) and other aspects.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Esfandyari, Maryam; Heravi, Majid; Oskooie, Hossein; Fotouhi, Lida; Tajbakhsh, Mahmood; Bamoharram, Fatemeh published an article in 2017, the title of the article was H3PW12O40: an efficient and green catalyst for the facile and selective oxidation of sulfides to sulfoxides, applied to the last step of the synthesis of omeprazole.Application In Synthesis of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole And the article contains the following content:

Omeprazole, (6-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl)-1H-benzimidazole) is a well-established prescribed drug, exhibits proton pump inhibitor activity. In this work, a novel, facile, economical and selective oxidation approach using H3PW12O40 as Keggin type heteropolyacids along with H2O2 in the last step of the conventional synthesis of this compound as well as its derivatives under environmental-benign conditions, is reported. This protocol can be well adopted for pilot plant scale giving a high pure pharmacopeia grade material. Our synthetic route involves the use of various heteropolyacids as heterogeneous catalysts. Due to the obtained results, it was concluded that Keggin type heteropolyacid , is an effective catalyst for this purpose. The optimized condition for the last step of this synthesis was applied to the synthesis of lansoprazole, pantoprazole, and rabeprazole. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Application In Synthesis of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

The Article related to heteropolyacid omeprazole sulfoxide oxidation green catalyst proton pump inhibitor, Catalysis, Reaction Kinetics, and Inorganic Reaction Mechanisms: Catalytic Reactions and other aspects.Application In Synthesis of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On November 15, 2013, Dai, Wen; Li, Jun; Chen, Bo; Li, Guosong; Lv, Ying; Wang, Lianyue; Gao, Shuang published an article.Related Products of 73590-85-9 The title of the article was Asymmetric Oxidation Catalysis by a Porphyrin-Inspired Manganese Complex: Highly Enantioselective Sulfoxidation with a Wide Substrate Scope. And the article contained the following:

The first genuinely promising porphyrin-inspired manganese-catalyzed asym. sulfoxidation method using hydrogen peroxide has been successfully developed, allowing for rapidly oxidation (0.5-1.0 h) of a wide variety of sulfides in high yields with excellent enantioselectivities (up to >99% ee). E.g., in presence of Mn(OTf)2, AcOH, and the porphyrin-inspired ligand (I), asym. oxidation of 3-ClC6H4SMe by hydrogen peroxide gave 82% sulfoxide (II, 97% ee). The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Related Products of 73590-85-9

The Article related to manganese ligand catalyst asym oxidation sulfide, enantioselective synthesis sulfoxide, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Sulfoxides and Sulfones and other aspects.Related Products of 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Fu, Zi-Hao; Tian, Hao-Dong; Ni, Shao-Fei; Wright, James S.; Li, Ming; Wen, Li-Rong; Zhang, Lin-Bao published an article in 2022, the title of the article was Scalable selective electrochemical oxidation of sulfides to sulfoxides.Safety of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole And the article contains the following content:

An electrochem. protocol for the selective oxidation of sulfides RSR1 (R = Ph, 2-bromophenyl, pyridin-2-yl, etc.; R1 = Me, 3-hydroxypropyl, cyclohexyl, etc.) and e.g., dibenzothiophene to sulfoxides RS(O)R1 and dibenzothiophene sulfoxide has been developed in NaCl that plays a dual role: (1) as an electrolyte for the electrochem. transformations and (2) as a redox mediator to avoid oxidation of sensitive functional groups. Instead of a traditional oxidant, this methodol. utilized traceless electrons as an ideal oxidant using anodic oxidation to access sulfoxides in good to excellent yields at ambient temperature This metal-free electrochem. protocol is simple, environmentally friendly, and compatible with various sensitive functional groups using mixed acetone/water as the green solvent. Moreover, the cost-effective graphite felt electrodes can be reused up to ten times without loss of electrochem. activity. The methodol. could be easily conducted on a gram or even a decagram scale. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Safety of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

The Article related to sulfoxide preparation green chem, sulfide scalable electrochem oxidation, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Sulfoxides and Sulfones and other aspects.Safety of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On November 25, 2015, Guo, Qirun; Hu, Yonghong; Yang, Wenge; Zhang, Tuan; Wu, Keyi; Yang, Shouhai; Shi, Ying published an article.Category: imidazoles-derivatives The title of the article was Thermodynamic models for determination of the solubility of omeprazole sulfide in (ethanol + ethyl acetate) binary solvent mixtures. And the article contained the following:

The solubility of omeprazole sulfide in (ethanol + Et acetate) binary solvent mixtures was measured within the temperature range from 277.65 to 333.15 K. The exptl. data were fitted using CNIBS/R-K equation and the Jouyban-Acree equation, resp. All the two equations were proven to give good representations of the exptl. values. Computational results showed that the CNIBS/R-K equation was superior to the other equation. The thermodn. properties of the solution process, including the Gibbs free energy, enthalpy and entropy, were calculated by the van’t Hoff anal. The values of both the enthalpy change and the standard molar Gibbs free energy change of solution were pos., which indicated that the process was endothermic. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Category: imidazoles-derivatives

The Article related to omeprazole sulfide ethanol ethyl acetate solvent mixture thermodn solubility, Phase Equilibriums, Chemical Equilibriums, and Solutions: Nonelectrolytic Solutions and other aspects.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem