Seenivasaperumal, Muthu et al. published their research in Advanced Synthesis & Catalysis in 2009 |CAS: 73590-85-9

The Article related to mechanism asym sulfoxidation esomeprazole process effect imidazole backbone enantioselection, Physical Organic Chemistry: Stereochemistry and Stereochemical Relationships, Including Conformational Inversions and Rotational Isomerization and other aspects.Quality Control of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

On April 30, 2009, Seenivasaperumal, Muthu; Federsel, Hans-Jurgen; Szabo, Kalman J. published an article.Quality Control of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole The title of the article was Mechanism of the asymmetric sulfoxidation in the esomeprazole process: effects of the imidazole backbone for the enantioselection. And the article contained the following:

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

The Article related to mechanism asym sulfoxidation esomeprazole process effect imidazole backbone enantioselection, Physical Organic Chemistry: Stereochemistry and Stereochemical Relationships, Including Conformational Inversions and Rotational Isomerization and other aspects.Quality Control of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Shen, Chao et al. published their research in Catalysis Communications in 2017 |CAS: 73590-85-9

The Article related to reusable slica support chitosan vanadium complex catalyst preparation, aryl alkyl sulfide chitosan vanadium complex catalyst sulfoxidation, sulfoxide aryl alkyl enantioselective preparation and other aspects.Related Products of 73590-85-9

On March 10, 2017, Shen, Chao; Qiao, Jun; Zhao, Linwei; Zheng, Kai; Jin, Jianzhong; Zhang, Pengfei published an article.Related Products of 73590-85-9 The title of the article was An efficient silica supported Chitosan@vanadium catalyst for asymmetric sulfoxidation and its application in the synthesis of esomeprazole. And the article contained the following:

A new type of silica supported chitosan@vanadium complex was used as a highly active heterogeneous catalyst for asym. oxidation of aryl alkyl sulfides. With the economic aqueous H2O2 (30%) as the oxidant, the oxidation products were obtained in high yields (up to 95%) with good enantioselectivities (up to 68% ee). It was noted that the marketed drug Nexium (first proton-pump inhibitor, esomeprazole) was synthesized easily by the newly developed asym. sulfoxidation reaction. In addition, the highly active catalyst was reused five times without losing its catalytic activity. 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 reusable slica support chitosan vanadium complex catalyst preparation, aryl alkyl sulfide chitosan vanadium complex catalyst sulfoxidation, sulfoxide aryl alkyl enantioselective preparation and other aspects.Related Products of 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Boix, C. et al. published their research in Science of the Total Environment in 2014 |CAS: 73590-85-9

The Article related to omeprazole metabolite wastewater surface water urine analysis sample pollution, metabolites, omeprazole, time-of-flight mass spectrometry, triple quadrupole mass spectrometry, urine, water samples and other aspects.Recommanded Product: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

On January 15, 2014, Boix, C.; Ibanez, M.; Zamora, T.; Sancho, J. V.; Niessen, W. M. A.; Hernandez, F. published an article.Recommanded Product: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole The title of the article was Identification of new omeprazole metabolites in wastewaters and surface waters. And the article contained the following:

Omeprazole is 1 of the world-wide most consumed pharmaceuticals for treatment of gastric diseases. As opposed to other frequently used pharmaceuticals, omeprazole is scarcely detected in urban wastewaters and environmental waters. This was corroborated in a previous research, where parent omeprazole was not detected while 4 transformation products (TPs), mainly resulting from hydrolysis, were found in effluent wastewaters and surface waters. However, the low abundance of omeprazole TPs in the H2O samples together with the fact that omeprazole suffers an extensive metabolism, with a wide range of excretion rates (between 0.01 and 30)̂, suggests that human urinary metabolites should be studied in the H2O environment. The results obtained in excretion tests after administration of a 40 mg omeprazole dose in 3 healthy volunteers are reported. Anal. by liquid chromatog. coupled to hybrid quadrupole time-of-flight mass spectrometry (LC-QTOF MS) reported low concentrations of omeprazole in urine. Up to 20-four omeprazole metabolites (OMs) were detected and tentatively elucidated. The most relevant OM was an omeprazole isomer, which obviously presented the same exact mass (m/z 346.1225), but also shared a major common fragment at m/z 198.0589. Subsequent analyses of surface H2O and effluent wastewater samples by both LC-QTOF MS and LC-MS/MS with triple quadrupole revealed that this metabolite (named as OM10) was the compound most frequently detected in H2O samples, followed by OM14a and OM14b. Up to the knowledge, OM10 had not been used before as urinary biomarker of omeprazole in waters. On the contrary, parent omeprazole was never detected in any of the H2O samples. After this research, it seems clear that monitoring the presence of omeprazole in the aquatic environment should be focused on the OMs suggested in this article instead of the parent compound 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: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

The Article related to omeprazole metabolite wastewater surface water urine analysis sample pollution, metabolites, omeprazole, time-of-flight mass spectrometry, triple quadrupole mass spectrometry, urine, water samples and other aspects.Recommanded Product: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Nevado, Juan Jose Berzas et al. published their research in Journal of Pharmaceutical and Biomedical Analysis in 2014 |CAS: 73590-85-9

The Article related to omeprazole metabolite capillary electrophoresis electrospray ionization mass spectrometry, capillary electrophoresis-mass spectrometry, human urine, metabolites, omeprazole, pharmacokinetics and other aspects.COA of Formula: C17H19N3O2S

On April 15, 2014, Nevado, Juan Jose Berzas; Penalvo, Gregorio Castaneda; Dorado, Rosa Maria Rodriguez; Robledo, Virginia Rodriguez published an article.COA of Formula: C17H19N3O2S The title of the article was Simultaneous determination of omeprazole and their main metabolites in human urine samples by capillary electrophoresis using electrospray ionization-mass spectrometry detection. And the article contained the following:

The authors report a novel method for the simultaneous determination of omeprazole and their main metabolites (omeprazole sulfide, omeprazole sulfone and 5-hydroxy omeprazole) in human urine samples. For this purpose, two new capillary electrophoresis (CE) methods were developed for the simultaneous determination of target compounds, using initially diode-array for optical detection and electrospray ionization-mass spectrometry (ESI-MS) for metabolites identification and identity confirmation. A new metabolite (5-hydroxysulfide omeprazole) was identified by electrospray ionization multi-stage mass spectrometry (ESI-MS2) fragment which was then used to support the proposed chem. structure. Pharmacokinetic results using CE method were compared with those obtained when a HPLC method was used. Equivalent pharmacokinetics profiles resulted when any anal. methods were carried out. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).COA of Formula: C17H19N3O2S

The Article related to omeprazole metabolite capillary electrophoresis electrospray ionization mass spectrometry, capillary electrophoresis-mass spectrometry, human urine, metabolites, omeprazole, pharmacokinetics and other aspects.COA of Formula: C17H19N3O2S

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Shen, Chao et al. published their research in Catalysis Communications in 2017 |CAS: 73590-85-9

The Article related to reusable slica support chitosan vanadium complex catalyst preparation, aryl alkyl sulfide chitosan vanadium complex catalyst sulfoxidation, sulfoxide aryl alkyl enantioselective preparation and other aspects.Related Products of 73590-85-9

On March 10, 2017, Shen, Chao; Qiao, Jun; Zhao, Linwei; Zheng, Kai; Jin, Jianzhong; Zhang, Pengfei published an article.Related Products of 73590-85-9 The title of the article was An efficient silica supported Chitosan@vanadium catalyst for asymmetric sulfoxidation and its application in the synthesis of esomeprazole. And the article contained the following:

A new type of silica supported chitosan@vanadium complex was used as a highly active heterogeneous catalyst for asym. oxidation of aryl alkyl sulfides. With the economic aqueous H2O2 (30%) as the oxidant, the oxidation products were obtained in high yields (up to 95%) with good enantioselectivities (up to 68% ee). It was noted that the marketed drug Nexium (first proton-pump inhibitor, esomeprazole) was synthesized easily by the newly developed asym. sulfoxidation reaction. In addition, the highly active catalyst was reused five times without losing its catalytic activity. 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 reusable slica support chitosan vanadium complex catalyst preparation, aryl alkyl sulfide chitosan vanadium complex catalyst sulfoxidation, sulfoxide aryl alkyl enantioselective preparation and other aspects.Related Products of 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Nevado, Juan Jose Berzas et al. published their research in Journal of Pharmaceutical and Biomedical Analysis in 2014 |CAS: 73590-85-9

The Article related to omeprazole metabolite capillary electrophoresis electrospray ionization mass spectrometry, capillary electrophoresis-mass spectrometry, human urine, metabolites, omeprazole, pharmacokinetics and other aspects.COA of Formula: C17H19N3O2S

On April 15, 2014, Nevado, Juan Jose Berzas; Penalvo, Gregorio Castaneda; Dorado, Rosa Maria Rodriguez; Robledo, Virginia Rodriguez published an article.COA of Formula: C17H19N3O2S The title of the article was Simultaneous determination of omeprazole and their main metabolites in human urine samples by capillary electrophoresis using electrospray ionization-mass spectrometry detection. And the article contained the following:

The authors report a novel method for the simultaneous determination of omeprazole and their main metabolites (omeprazole sulfide, omeprazole sulfone and 5-hydroxy omeprazole) in human urine samples. For this purpose, two new capillary electrophoresis (CE) methods were developed for the simultaneous determination of target compounds, using initially diode-array for optical detection and electrospray ionization-mass spectrometry (ESI-MS) for metabolites identification and identity confirmation. A new metabolite (5-hydroxysulfide omeprazole) was identified by electrospray ionization multi-stage mass spectrometry (ESI-MS2) fragment which was then used to support the proposed chem. structure. Pharmacokinetic results using CE method were compared with those obtained when a HPLC method was used. Equivalent pharmacokinetics profiles resulted when any anal. methods were carried out. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).COA of Formula: C17H19N3O2S

The Article related to omeprazole metabolite capillary electrophoresis electrospray ionization mass spectrometry, capillary electrophoresis-mass spectrometry, human urine, metabolites, omeprazole, pharmacokinetics and other aspects.COA of Formula: C17H19N3O2S

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Boix, C. et al. published their research in Science of the Total Environment in 2014 |CAS: 73590-85-9

The Article related to omeprazole metabolite wastewater surface water urine analysis sample pollution, metabolites, omeprazole, time-of-flight mass spectrometry, triple quadrupole mass spectrometry, urine, water samples and other aspects.Recommanded Product: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

On January 15, 2014, Boix, C.; Ibanez, M.; Zamora, T.; Sancho, J. V.; Niessen, W. M. A.; Hernandez, F. published an article.Recommanded Product: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole The title of the article was Identification of new omeprazole metabolites in wastewaters and surface waters. And the article contained the following:

Omeprazole is 1 of the world-wide most consumed pharmaceuticals for treatment of gastric diseases. As opposed to other frequently used pharmaceuticals, omeprazole is scarcely detected in urban wastewaters and environmental waters. This was corroborated in a previous research, where parent omeprazole was not detected while 4 transformation products (TPs), mainly resulting from hydrolysis, were found in effluent wastewaters and surface waters. However, the low abundance of omeprazole TPs in the H2O samples together with the fact that omeprazole suffers an extensive metabolism, with a wide range of excretion rates (between 0.01 and 30)̂, suggests that human urinary metabolites should be studied in the H2O environment. The results obtained in excretion tests after administration of a 40 mg omeprazole dose in 3 healthy volunteers are reported. Anal. by liquid chromatog. coupled to hybrid quadrupole time-of-flight mass spectrometry (LC-QTOF MS) reported low concentrations of omeprazole in urine. Up to 20-four omeprazole metabolites (OMs) were detected and tentatively elucidated. The most relevant OM was an omeprazole isomer, which obviously presented the same exact mass (m/z 346.1225), but also shared a major common fragment at m/z 198.0589. Subsequent analyses of surface H2O and effluent wastewater samples by both LC-QTOF MS and LC-MS/MS with triple quadrupole revealed that this metabolite (named as OM10) was the compound most frequently detected in H2O samples, followed by OM14a and OM14b. Up to the knowledge, OM10 had not been used before as urinary biomarker of omeprazole in waters. On the contrary, parent omeprazole was never detected in any of the H2O samples. After this research, it seems clear that monitoring the presence of omeprazole in the aquatic environment should be focused on the OMs suggested in this article instead of the parent compound 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: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

The Article related to omeprazole metabolite wastewater surface water urine analysis sample pollution, metabolites, omeprazole, time-of-flight mass spectrometry, triple quadrupole mass spectrometry, urine, water samples and other aspects.Recommanded Product: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Ding, Fangwei et al. published their research in European Journal of Organic Chemistry in 2017 |CAS: 73590-85-9

The Article related to sulfide green preparation, sulfoxide deoxygenation phenylsilane tris pentafluorophenyl borane catalyst, amine green preparation, deoxygenation amine oxide phenylsilane tris pentafluorophenyl borane catalyst and other aspects.Synthetic Route of 73590-85-9

Ding, Fangwei; Jiang, Yanqiu; Gan, Shaoyan; Bao, Robert Li-Yuan; Lin, Kaifeng; Shi, Lei published an article in 2017, the title of the article was B(C6F5)3-Catalyzed Deoxygenation of Sulfoxides and Amine N-Oxides with Hydrosilanes.Synthetic Route of 73590-85-9 And the article contains the following content:

An efficient strategy for the deoxygenation of sulfoxides and amine N-oxides by using B(C6F5)3 and hydrosilanes was developed. This method provided the corresponding aromatic and aliphatic sulfides/amines in good to high yields and showed good functional-group tolerance under mild conditions. This protocol should be very useful in the future because of its ease of operation, the environmentally friendly reaction conditions and wide scope. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Synthetic Route of 73590-85-9

The Article related to sulfide green preparation, sulfoxide deoxygenation phenylsilane tris pentafluorophenyl borane catalyst, amine green preparation, deoxygenation amine oxide phenylsilane tris pentafluorophenyl borane catalyst and other aspects.Synthetic Route of 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Jang, Hyun-Hee et al. published their research in Biotechnology Letters in 2017 |CAS: 73590-85-9

The Article related to regioselective carbon hydrogen hydroxylation omeprazole sulfide bacillus megaterium cyp102a1, 5-hydroxyomeprazole sulphide, cyp102a1 mutant, human metabolite, hydroxylation, omeprazole sulfide, regioselectivity and other aspects.Synthetic Route of 73590-85-9

On January 31, 2017, Jang, Hyun-Hee; Ryu, Sang-Hoon; Le, Thien-Kim; Doan, Tiep Thi My; Nguyen, Thi Huong Ha; Park, Ki Deok; Yim, Da-Eun; Kim, Dong-Hyun; Kang, Choong-Kyung; Ahn, Taeho; Kang, Hyung-Sik; Yun, Chul-Ho published an article.Synthetic Route of 73590-85-9 The title of the article was Regioselective C-H hydroxylation of omeprazole sulfide by Bacillus megaterium CYP102A1 to produce a human metabolite. And the article contained the following:

Objectives: To find a simple enzymic strategy for the efficient synthesis of the expensive 5′-hydroxyomeprazole sulfide, a recently identified minor human metabolite, from omeprazole sulfide, which is an inexpensive substrate. Results: The practical synthetic strategy for the 5′-OH omeprazole sulfide was accomplished with a set of highly active CYP102A1 mutants, which were obtained by blue colony screening from CYP102A1 libraries with a high conversion yield. The mutant and even the wild-type enzyme of CYP102A1 catalyzed the high regioselective (98 %) C-H hydroxylation of omeprazole sulfide to 5′-OH omeprazole sulfide with a high conversion yield (85-90 %). Conclusions: A highly efficient synthesis of 5′-OH omeprazole sulfide was developed using CYP102A1 from Bacillus megaterium as a biocatalyst. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Synthetic Route of 73590-85-9

The Article related to regioselective carbon hydrogen hydroxylation omeprazole sulfide bacillus megaterium cyp102a1, 5-hydroxyomeprazole sulphide, cyp102a1 mutant, human metabolite, hydroxylation, omeprazole sulfide, regioselectivity and other aspects.Synthetic Route of 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Talsi, Evgenii P. et al. published their research in Catalysis Today in 2017 |CAS: 73590-85-9

The Article related to titanium salan complex catalyst preparation, pyridylmethylthiobenzimidazole titanium salan complex catalyst sulfoxidation, pyridylmethyl benzimidazolyl sulfoxide preparation chemoselective enantioselective green chem and other aspects.Category: imidazoles-derivatives

On January 1, 2017, Talsi, Evgenii P.; Bryliakov, Konstantin P. published an article.Category: imidazoles-derivatives The title of the article was Ti-Salan catalyzed asymmetric sulfoxidation of pyridylmethylthiobenzimidazoles to optically pure proton pump inhibitors. And the article contained the following:

The asym. sulfoxidation of two pyridylmethylthiobenzimidazoles to anti-ulcer drugs of the PPI family (S)-omeprazole and (R)-lansoprazole with hydrogen peroxide, mediated by a series of chiral titanium(IV) salan complexes was reported. High sulfoxide yields (up to >95%) and enantioselectivities (up to 94% ee) were achieved. The introduction of electron-withdrawing substituents leaded to less active and less enantioselective catalysts. Like for the previously reported Ti-salalen catalyzed sulfoxidations, the temperature dependence of the sulfoxidation enantioselectivity in the presence of Ti-salan complexes was nonmonotonic, demonstrating isoinversion behavior with decreasing temperature The oxidation was likely rate-limited by the formation of the active (presumably peroxotitanium(IV)) species, followed by a faster oxygen transfer to the substrate. 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 titanium salan complex catalyst preparation, pyridylmethylthiobenzimidazole titanium salan complex catalyst sulfoxidation, pyridylmethyl benzimidazolyl sulfoxide preparation chemoselective enantioselective green chem and other aspects.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem