Category: 280752-78-5

On June 15, 2007, Juhasz, Laszlo; Docsa, Tibor; Brunyaszki, Attila; Gergely, Pal; Antus, Sandor published an article.Electric Literature of 280752-78-5 The title of the article was Synthesis and glycogen phosphorylase inhibitor activity of 2,3-dihydrobenzo[1,4]dioxin derivatives. And the article contained the following:

Novel 5-benzyl and 5-benzylidene-thiazolidine-2,4-diones carrying 2,3-dihydrobenzo[1,4]dioxin pharmacophore were synthesized and their glycogen phosphorylase inhibitor activity was also studied. Compound I possesses a high glycogen phosphorylase inhibitory activity with a Ki = 10-12 μM. The experimental process involved the reaction of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol(cas: 280752-78-5).Electric Literature of 280752-78-5

The Article related to glycogen phosphorylase inhibitor antidiabetic dihydrobenzodioxin thiazolidinedione preparation sar, Pharmacology: Structure-Activity and other aspects.Electric Literature of 280752-78-5

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On May 13, 2004, Linn, David Martin; Wong, Erik Ho Fong published a patent.Safety of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol The title of the patent was Preparation of azabicyclic α7 nicotinic acetylcholine agonists for the treatment of glaucoma and retinal neuropathy. And the patent contained the following:

The invention provides a use or method of treating glaucoma, diabetic retinopathy, or age-related macular degeneration by the administration of azabicycles (azabicyclo-N(R1)C(:X)W (I); X = O, S; R1 = H, alkyl, cycloalkyl, haloalkyl, substituted Ph, substituted naphthyl; W = substituted Ph, (un)substituted 5- or 6-membered heterocyclyl, etc.; addnl. details are given in the claims) that are α7 nAChR agonists (no data) to a mammal in need thereof. Although the methods of preparation are not claimed, many example preparations of intermediates are included. For example, intermediate exo-(4S)-3-amino-1-azabicyclo[2.2.1]heptane bis(p-toluenesulfonate) was prepared in 8 steps (68, 62, 76, 100, 77, 94, 46, 84 % yields, resp.) starting with reaction of benzoyl chloride with 2-nitroethanol to give 2-(benzoyloxy)-1-nitroethane, reaction of Et E-4-bromo-2-butenoate with benzylamine to give Et E-4-(benzylamino)-2-butenoate, reaction of these 2 products to give trans-4-nitro-1-(phenylmethyl)-3-pyrrolidineacetic acid Et ester, reduction to trans-4-amino-1-(phenylmethyl)-3-pyrrolidineacetic acid Et ester, N-protection, reduction to trans-3-(tert-butoxycarbonylamino)-4-(2-hydroxyethyl)-1-(phenylmethyl)pyrrolidine, chromatog. resolution, cyclization of the (+)-enantiomer to give exo-(4S)-3-(tert-butoxycarbonylamino)-1-azabicyclo[2.2.1]heptane and finally deprotection. In another example, N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-4-bromo-1H-pyrazole-1-carboxamide hydrochloride was prepared (25 %) by treating 4-bromopyrazole with phosgene followed by (R)-(+)-3-aminoquinuclidine dihydrochloride and excess Et3N, followed by NaOH. The experimental process involved the reaction of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol(cas: 280752-78-5).Safety of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

The Article related to azabicycle preparation nicotinic acetylcholine agonist glaucoma retinal neuropathy, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Safety of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

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On July 20, 2018, Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu published an article.HPLC of Formula: 280752-78-5 The title of the article was Enantioselective Access to Chiral 2-Substituted 2,3-Dihydrobenzo[1,4]dioxane Derivatives through Rh-Catalyzed Asymmetric Hydrogenation. And the article contained the following:

Rh-catalyzed asym. hydrogenation of various benzo[b][1,4]dioxine derivatives, e.g. I, was successfully developed to prepare chiral 2-substituted 2,3-dihydrobenzo[1,4]dioxane derivatives using ZhaoPhos and N-methylation of ZhaoPhos ligands with high yields and excellent enantioselectivities (up to 99% yield, >99% enantiomeric excess (ee), turnover number (TON) = 24,000). Moreover, this asym. hydrogenation methodol., as the key step with up to 10 000 TON, was successfully applied to develop highly efficient synthetic routes for the construction of some important biol. active mols., such as MKC-242, WB4101, BSF-190555 and (R)-doxazosin·HCl. The experimental process involved the reaction of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol(cas: 280752-78-5).HPLC of Formula: 280752-78-5

The Article related to rhodium catalyst hydrogenation benzodioxin asym preparation, Heterocyclic Compounds (More Than One Hetero Atom): Dioxanes and other aspects.HPLC of Formula: 280752-78-5

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On May 22, 2003, Walker, Daniel P.; Jacobsen, Jon E.; Acker, Brad A.; Groppi, Vincent E.; Piotrowski, David W. published a patent.Application of 280752-78-5 The title of the patent was Preparation of N-(azabicyclyl)arylamides for therapeutic use as nicotinic acetylcholine receptor agonists. And the patent contained the following:

N-(azabicyclyl)arylamides, such as RNR1C(:X)W [R = azabicyclyl; R1 = H, alkyl, cycloalkyl, haloalkyl, aryl; W = heteroaryl; X = O, S], were prepared for therapeutic use as nicotinic acetylcholine receptor agonists. These amides are useful for the treatment of central nervous system disorders, such as cognitive and attention deficit symptoms of Alzheimer’s, neurodegeneration associated with diseases such as Alzheimer’s disease, pre-senile dementia (mild cognitive impairment), senile dementia, schizophrenia, psychosis, attention deficit disorder, attention deficit hyperactivity disorder, mood and affective disorders, amyotrophic lateral sclerosis, borderline personality disorder, traumatic brain injury, behavioral and cognitive problems associated with brain tumors, AIDS dementia complex, dementia associated with Down’s syndrome, dementia associated with Lewy Bodies, Huntington’s disease, depression, general anxiety disorder, age-related macular degeneration, Parkinson’s disease, tardive dyskinesia, Pick’s disease, post traumatic stress disorder, dysregulation of food intake including bulimia and anorexia nervosa, withdrawal symptoms associated with smoking cessation and dependent drug cessation, Gilles de la Tourette’s Syndrome, glaucoma, neurodegeneration associated with glaucoma, or symptoms associated with pain. Thus, amide I was prepared in 71% yield by an amidation reaction of 1,4-benzodioxane-6-carboxylic acid with 3-(R)-aminoquinuclidine dihydrochloride using DIEA and HATU in MeCN at -10°. The prepared amides were assayed for human α7-5HT3 receptor binding activity. The experimental process involved the reaction of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol(cas: 280752-78-5).Application of 280752-78-5

The Article related to azabicyclic heteroaryl amide preparation nicotinic acetylcholine receptor agonist, Alkaloids: Alkaloids Containing One Nitrogen Atom At A Bridgehead and other aspects.Application of 280752-78-5

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On June 24, 2004, Corbett, Jeffrey Wayne; Groppi, Vincent Edward, Jr. published a patent.Name: (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol The title of the patent was A preparation of azabicycloalkane derivatives, useful as α7 nicotinic acetylcholine receptor (α7 nAChR) agonists. And the patent contained the following:

The invention relates to azabicycloalkane derivatives of formula azabicyclo-N(R1)-C(:X)-W [wherein: R1 is H, (cyclo)alkyl, or haloalkyl, etc.; X is O or S; W is a substituted benzene], useful as α7 nAChR agonists. Pharmacokinetics of the prepared compounds were evaluated (no biol. data). Blood-brain barrier penetration was investigated (no biol. data). For instance, chiral azabicycloheptane derivative I was prepared via addition of Me 3-bromopropargylate to N-Boc-pyrrole, reduction of the obtained azabicyclo[2.2.1]heptadiene II, hydrolysis of the obtained azabicycloheptane derivative III (R2 = OMe), reaction of the carboxylic acid III (R2 = OH) with diphenylphosphoryl azide and benzyl alc., resolution of the obtained exo-derivative IV, and hydrogenation. The experimental process involved the reaction of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol(cas: 280752-78-5).Name: (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

The Article related to azabicycloalkane preparation alpha7 nachr agonist nicotinic acetylcholine receptor antialzheimer, pyrrole bromo propargylate addition reduction resolution, Alicyclic Compounds: Bicyclic Compounds, Including Azulenes, Heptalenes, and Pentalenes and other aspects.Name: (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

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On August 5, 2004, Groppi, Vincent Edward, Jr.; Rogers, Bruce Nelsen; Rudmann, Daniel Gregory published a patent.Name: (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol The title of the patent was Treatment of diseases with alpha-7 NACh receptor full agonists. And the patent contained the following:

The present invention relates to compositions and methods to treat diseases or conditions with alpha-7 nicotinic acetylcholine receptor (AChR) full agonists by decreasing levels of tumor necrosis factor-alpha and/or by stimulating vascular angiogenesis. The experimental process involved the reaction of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol(cas: 280752-78-5).Name: (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

The Article related to nicotinic acetylcholine receptor agonist quinuclidinylheteroarylamide cancer diabetes angiogenesis therapy, Pharmacology: Effects Of Nervous System- and Behavior-Affecting Drugs and Neuromuscular Agents and other aspects.Name: (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

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On June 24, 2004, Groppi, Vincent Edward, Jr.; Jacobsen, Eric Jon; Myers, Jason Kenneth; Piotrowski, David Walter; Rogers, Bruce Nelsen; Walker, Daniel Patrick; Wishka, Donn Gregory published a patent.Product Details of 280752-78-5 The title of the patent was Preparation of N-(quinuclidinyl)heteroarylamides as nicotinic acetylcholine receptor agonists for use in combination therapy for the treatment of ADHD. And the patent contained the following:

Title N-(1-azabicyclo[2.2.2]octyl)heteroarylamides I and analogs [wherein X = o, S; R1 = H, (halo)alkyl, cycloalkyl, substituted Ph, naphthyl; R2 = independently halo, cycloalkyl, aryl, (un)substituted alkyl; m = 0-1; n = 0-1; with the proviso that m + n = 1; W = (un)substituted Ph, heterocyclyl, heteroaryl; or pharmaceutically acceptable salts, racemic mixtures, or pure enantiomers thereof] were prepared as α7 nicotinic acetylcholine receptor (nAChR) full agonists (no data). For example, reaction of phosgene with 4-bromopyrazole in EtOAc, followed by coupling with (+)-3-aminoquinuclidine•2HCl provided II•HCl (25%). The invention provides for compositions of I with psychostimulants and/or monoamine reuptake inhibitors for the treatment of attention deficit hyperactivity disorder (ADHD). The experimental process involved the reaction of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol(cas: 280752-78-5).Product Details of 280752-78-5

The Article related to quinuclidinyl heteroarylamide preparation nicotinic acetylcholine receptor agonist adhd treatment, azabicyclooctyl heteroarylamide preparation composition nachr agonist adhd treatment and other aspects.Product Details of 280752-78-5

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On December 1, 2018, Guo, Bin; Guo, Shimeng; Huang, Jing; Li, Jingya; Li, Jia; Chen, Qian; Zhou, Xianli; Xie, Xin; Yang, Yushe published an article.Product Details of 280752-78-5 The title of the article was Design and optimization of 2,3-dihydrobenzo[b][1,4]dioxine propanoic acids as novel GPR40 agonists with improved pharmacokinetic and safety profiles. And the article contained the following:

GPR40 has become a new potential therapeutic target for the treatment of diabetes due to its role in mediating the enhancement of glucose-stimulated insulin secretion in pancreatic β cells with a low risk of hypoglycemia. As an effort to extend the chem. space and identify structurally distinct GPR40 agonists with improved liver safety, a novel series of fused-ring Ph propanoic acid analogs were designed. Comprehensive structure-activity relationship studies around novel scaffolds were conducted and led to several analogs exhibited potent GPR40 agonistic activities and high selectivity against other fatty acid receptors. Further evaluation of pharmacokinetic (PK) profiles and in vivo efficacy identified compound I with excellent PK properties and significant glucose-lowering efficacy during an oral glucose tolerance test. In addition, compound I displayed lower hepatobiliary transporter inhibition and favorable druggability. All results indicate that compound I is a promising candidate for further development. The experimental process involved the reaction of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol(cas: 280752-78-5).Product Details of 280752-78-5

The Article related to dihydrobenzodioxine propanoic acid preparation gpr40 agonist antidiabetic pharmacokinetic profile, 2,3-dihydrobenzo[b][1,4]dioxine, gpr40 agonist, insulin secretion, type 2 diabetes mellitus and other aspects.Product Details of 280752-78-5

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On October 12, 2000, Link, James; Liu, Gang; Pei, Zhonghua; Von Geldern, Thomas W.; Winn, Martin; Xin, Zhili; Wang, Sheldon; Boyd, Steven A.; Zhu, Gui-Dong; Freeman, Jennifer C.; Gunawardana, Indrani W.; Staeger, Michael A.; Jae, Hwan-soo; Lynch, John K. published a patent.Category: alcohols-buliding-blocks The title of the patent was Preparation of 2- or 4-(phenylthio)cinnamides as cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds. And the patent contained the following:

The title compounds (I) [wherein R1-R5 = independently H, halo, (halo)alkyl, alkoxy, cyano, NO2, CHO, and least one of R1 or R3 is an (un)substituted cis- or trans-cinnamide; Ar = (un)substituted (hetero)aryl] were prepared as cell adhesion inhibitors for the treatment of inflammatory and immune diseases. Examples include syntheses for 443 invention compounds and data for 3 bioassays. For instance, a mixture of 2-[(2,4-dichlorophenyl)thio]benzaldehyde (preparation given), malonic acid, piperidine in anhydrous pyridine was heated at 110° for 2 h and then treated with aqueous HCl to give trans-2-[(2,4-dichlorophenyl)thio]cinnamic acid (91%). Conversion to the acid chloride followed by amidation with 6-amino-1-hexanol gave (E)-II (90%). In an integrin LFA-1/ICAM-1 biochem. interaction assay, I demonstrated inhibition at 4 μM. In cell-based adhesion assays which measure the ability of test compounds to block adherence of JY-8 cells (a human EBV-transformed B cell line expressing LFA-1 on its surface) to immobilized ICAM-1 or ICAM-3, I exhibited blocking activity at 4 μM and 0.6 μM, resp. The experimental process involved the reaction of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol(cas: 280752-78-5).Category: alcohols-buliding-blocks

The Article related to phenylthio cinnamide preparation cell adhesion inhibitor, aminocarbonylethenylphenyl phenyl sulfide preparation antiinflammatory, sulfide aminocarbonylethenylphenyl phenyl preparation immunosuppressant and other aspects.Category: alcohols-buliding-blocks

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On July 6, 2000, Link, James; Liu, Gang; Pei, Zhonghua; Von Geldern, Tom; Winn, Martin; Xin, Zhili; Boyd, Steven A.; Jae, Hwan-Soo; Lynch, John K.; Zhu, Gui-Dong; Freeman, Jennifer C.; Gunawardana, Indrani W.; Staeger, Michael A. published a patent.Quality Control of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol The title of the patent was Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds. And the patent contained the following:

The present invention relates to novel cinnamide compounds that are useful for treating inflammatory and immune diseases, to pharmaceutical compositions containing these compounds, and to methods of inhibiting inflammation or suppressing immune response in a mammal. Among the approx. 400 trans-arylthiocinnamamide title compounds, prepared by standard methods, were 6-benzodioxanyl 2-trifluoromethyl-4-[(E)-2-[3-(R)-(ethoxycarbonyl)piperidinocarbonyl]ethenyl]phenyl sulfide (I), 2-ethoxyphenyl 2-trifluoromethyl-4-[(E)-2-[2-carboxy-4-(methoxycarbonyl)-1-piperazinylcarbonyl]ethenyl]phenyl sulfide (II) and 2-isopropylphenyl 2-nitro-4-[(E)-2-[3-(2-oxo-1-pyrrolidinyl)-1-propylaminocarbonyl]ethenyl]phenyl sulfide (III). The abilities of the title compounds to antagonize the interaction between ICAM-1 and LFA-1 were quantified using both biochem. and cell-based adhesion assays. E.g., compounds I-III exhibited 98% inhibition @ 4μM. The experimental process involved the reaction of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol(cas: 280752-78-5).Quality Control of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

The Article related to antiinflammatory arylthiocinnamamide preparation, immune suppressive arylthiocinnamamide preparation, cell adhesion inhibitor arylthiocinnamamide preparation, cinnamamide arylthio hetaryl preparation and other aspects.Quality Control of (6-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

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