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Synthesis of chiral nonracemic 1-(2-pyridinyl)ethylamines: Stereospecific introduction of amino function onto the 2-pyridinylmethyl carbon center

Stereospecific substitutions of optically pure 1-(pyridinyl)ethyl methanesulfonates with various amines are described. The reaction of (R)- or (S)-1-(2-pyridinyl)ethyl methanesulfonate with primary amines, including amino acid esters, gives N-substituted (S)- or (R)-1-(2-pyridinyl)ethylamines (4) with inversion of the configuration. Secondary cyclic amines are also reacted with (R)-2 to give the corresponding substituted amines (5) in excellent yields. Optically pure and meso triamine ligands having two pyridine rings, (S,S)-4f and meso-4f, (S,S)-9e, (S,R)-9e, and (S,S)-9f, have been prepared in stereochemically pure form by this method. Not only the substitution reaction of optically active 2 but also that of 1-(4-pyridinyl)ethyl and 1-(3-pyridinyl)ethyl methanesulfonates 11 and 14 take place stereospecifcally with inversion of the chiral center.

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Reference£º
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS

Disclosed herein are cannabinoid receptor ligands of formula (I) wherein A1, A5, Rx, X4, and z are as defined in the specification. Compositions comprising such compounds, and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

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Reference£º
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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TETRA- AND PENTASUBSTITUTED BENZIMIDAZOLIUM COMPOUNDS USEFUL IN THE TREATMENT OF RESPIRATORY DISEASES

The present invention relates to compounds of formula (I), or the tautomers or pharmacologically acceptable acid addition salts thereof, wherein R1, R2, R3, R4, X, and Z have one of the meanings as defined in the specification, to the use of compounds of formula (I) as a medicament, to pharmaceutical composition comprising at least one com? pound of formula (I), as well as to medicament combinations containing one or more compounds of formula (I).

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Reference£º
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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1,4-Benzofused urea compounds useful in treating cytokine mediated diseases

Disclosed are 1,4-disubstituted benzo-fused urea compounds of formula (I): 1wherein Ar, X, A, L, and Q of formula(I) are defined herein. The compounds inhibit production of cytokines involved in inflammatory processes and are thus useful for treating diseases and pathological conditions involving inflammation such as chronic inflammatory disease. Also disclosed are processes for preparing these compounds and pharmaceutical compositions comprising these compounds.

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Reference£º
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Discovery of (S)-(Tetrahydrofuran-2-yl)methanamine

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MODULATORS OF AMYLOID BETA

The present invention relates to novel compounds of formula I and therapeutically acceptable salts thereof, their pharmaceutical compositions, processes for making them and their use as therapeutic methods for treatment and/or prevention of various diseases. In particular the invention relates to compounds, which inhibit the Ab40 and Ab42 production, increase the Ab37 and Ab38 production and maintain the Notch signaling and will be used for treatment and/or prevention of Ab-related pathologies such as Alzheimer’s disease. Downs syndrome and b-amyloid angiopathy, such as but not limited to cerebral amyloid angiopathy, hereditary cerebral hemorrhage, disorders associated with cognitive impairment, such as but not limited to MCI (“mild cognitive impairment”), Alzheimer’s disease, memory loss, attention deficit symptoms associated with Alzheimer’s disease, neurodegeneration associated with diseases such as Alzheimer’s disease or dementia including dementia of mixed vascular and degenerative origin, pre-senile dementia, senile dementia and dementia associated with Parkinson’s disease, progressive supranuclear palsy or cortical basal degeneration

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Reference£º
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Discovery of (S)-(Tetrahydrofuran-2-yl)methanamine

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Method of inhibiting angiogenesis

Compounds having the formula 1are angiogenesis inhibitors. Also disclosed are compositions containing the compounds, methods of making the compounds, and methods of treatment using the compounds.

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Reference£º
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Discovery of (S)-(Tetrahydrofuran-2-yl)methanamine

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Stereocontrolled synthesis of a complex library via elaboration of angular epoxyquinol scaffolds

We have accomplished the synthesis of a complex chemical library via elaboration of angular epoxyquinol scaffolds with distinct skeletal frameworks. The key strategy involves highly stereo-controlled [4 + 2] Diels-Alder cycloadditions of chiral, nonracemic epoxyquinol dienes to generate the scaffolds. Further scaffold diversification involves hydrogenation, epimerization, dehydration, and condensation of the carbonyl group with alkoxyamine and carbazate building blocks. Further elaboration of the scaffolds also provided new skeletal frameworks using hydroxyl-directed Diels-Alder cycloaddition and reductive N-N bond cleavage. The overall process afforded 244 highly complex and functionalized compounds. Preliminary biological screening of the library uncovered six compounds which showed significant inhibition of Hsp 72 induction.

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Reference£º
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Triplet reactivity and regio/stereoselectivity in the macrocyclization of diastereomeric ketoprofen-quencher conjugates via remote hydrogen abstractions

Intramolecular excited triplet state interactions in diastereomeric compounds composed of a benzophenone chromophore (ketoprofen) and various hydrogen donor moieties (tetrahydrofuran, isopropylbenzene) have been investigated by laser flash photolysis. The rate constants for hydrogen abstraction by excited triplet benzophenone are in the order of 10 4-105 s-1, with the highest reactivity for the tetrahydrofuran residue. A remarkable diastereodifferentiation, expressed in the triplet lifetimes of the carbonyl chromophore (e.g., 1.6 versus 2.7 mus), has been found for these compounds. With an alkylaromatic moiety as donor, related effects have been observed, albeit strongly dependent on the length of the spacer. The reactivity trend for the initial hydrogen transfer step is paralleled by the quantum yields of the overall photoreaction. The biradicals, formed via remote hydrogen abstraction, undergo intramolecular recombination to macrocyclic ring systems. The new photoproducts have been isolated and characterized by NMR spectroscopy. The stereochemistry of the macrocycles, which contain up to four asymmetric carbons, has been unambiguously assigned on the basis of single-crystal structures and/or NOE effects. Interestingly, a highly regio- and stereoselective macrocyclization has been found for the ketoprofen-tetrahydrofuran conjugates, where hydrogen abstraction from the less substituted carbon is exclusive; cisoid ring junction is always preferred over the transoid junction. The photoreaction is less regioselective for compounds with an isopropylbenzene residue. The reactivity and selectivity trends have been rationalized by DFT (B3LYP/6-31G*) calculations.

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Reference£º
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Resolution of certain asymmetric primary amines using lasalocid

Racemic modifications of optically active primary or tertiary amines are treated with lasalocid to form diastereomeric salts. The so-formed diastereomeric salts are separated and, subsequently, can be chemically decomposed to give the desired enantiomers of the amine. The resolving agent, lasalocid, is recovered in this process by precipitation or evaporation from organic solvents.

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Reference£º
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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HETEROCYCLIC CANNABINOID RECEPTOR ANTAGONISTS

The present invention relates to compounds of formula I and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with the modulation of CB1 receptors.

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Reference£º
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem