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The invention concerns compounds represented by general formula (I) wherein: Z represents a sulfur or oxygen atom; the groups R1 and R2, identical or different, represent each a alkyl group or an alkenyl group; X represents a CO, a CO2, an SO, or an SO2 and the group R represents an alkyl, aryl, alkenyl, or aralkyl group, provided that when Z represents an oxygen atom, X an SO2 and R a group (a), R1 and R2 do not both represent the methyl group. The invention also concerns methods for preparing said compounds, pharmaceutical compositions containing them and their use as promoter of gamma-aminobutyric acid and as medicine particularly designed for treating nervous disorders.

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Tetrahydrofuran – Wikipedia,
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All four stereoisomers of 2-alkyl-3,4-iminobutanic acid, a novel class of beta-amino acids bearing a chemically versatile aziridine ring, were synthesized starting with aspartic acid. The synthetic strategy involves the introduction of an alkyl group at the beta-position of fully protected optically active aspartic acid followed by the construction of an aziridine ring making use of the alpha-carboxylate and alpha-amino groups. The alpha-carboxylate was reduced to the corresponding alcohol, which was then subjected to cyclization to form an aziridine ring with the N-protected amino group. Removal of the protection groups yielded the target compounds.

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Tetrahydrofuran – Wikipedia,
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Academic researchers, R&D teams, teachers, students, policy makers and the media all rely on us to share knowledge that is reliable, accurate and cutting-edge. Safety of (S)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate

A compound represented by formula (1):Q1-Q2-To-N(R1) -Q3-N(R2)-T1-Q4 [wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6- membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 represents the following group: (wherein Q5 is an alkylene group having 1 to 8 carbon atoms, or the like); and T0 and T1 are carbonyl groups or the like], a salt thereof, a solvate thereof, or an N-oxide thereof.The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger’s disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after artificial valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.

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Tetrahydrofuran – Wikipedia,
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A general method has been developed for assigning the structures of nodularin, a potent hepatotoxin, tumor promoter, and protein phosphatase inhibitor, and minor components isolated from a cultured and a bloom sample of the cyanobacterium Nodularia spumigena. It consists of (1) FABMS analysis (determination of molecular weight and molecular formula), (2) 1H NMR spectroscopy on the parent compound and chiral GC analysis of an acid hydrolyzate (identification and stereochemistry of amino acid components), (3) ozonolysis followed by NaBH4 reduction (conversion to a linear peptide), and (4) FABMS/CID/MS analyses of the linear peptide and the parent compound (sequence analysis). The method has been employed in assigning structures to three new nodularins (2-4) and can be applied to other cyclic peptides containing alpha,beta-dehydroamino acid unit(s), especially the related microcystins, cyclic heptapeptide hepatotoxins. Two nodularins, [DMAdda3]nodularin (2) and [(6Z)Adda3]nodularin (3), were obtained from a bloom sample collected from Lake Ellesmere (New Zealand), and [D-Asp1]nodularin (4) was isolated from cultured cells (strain L-575). The LD50s of 2 and 4 were 150 and 75 mug/kg (ip, mice), respectively, but 3 did not show apparent toxicity at 2.0 mg/kg.

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Tetrahydrofuran – Wikipedia,
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Discovery of (S)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate

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Chiral N-protected beta-amino alcohols are easily obtained by NaBH4 reduction of mixed anhydrides of N-protected alpha-amino acids in an organic/aqueous medium. The alcohols obtained from side chain or main chain reduction of N-protected aspartic acid are converted in good yields into lactones.

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In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 87219-29-2, name is (S)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate, introducing its new discovery. Formula: C12H13NO4

1,4-Addition of benzylamine to 2(5H)-furanone followed by dialkylation of the 3-position with allylbromide gave (±)-4-benzyl-3,3-diallyl-2(3H)-furanone (8), which served as the intermediate for the synthesis of various N-substituted 4-amino-3,3-dipropyl-2(3H)-furanones (±)-9a-1. The compounds were evaluated for their capacity to potentiate or inhibit GABA-evoked currents in Xenopus laevis oocytes expressing recombinant alpha1beta2gamma2 GABAA receptors. The benzyl, ethyl, and allyl carbamates ((R)-9a (100 muM), (±)-9b (100 muM), (±)-9c (200 muM)) stimulated GABA currents by 279 ± 47%, 426 ± 8%. and 765 ± 61%, respectively, while the phenylcarboxamide (±)-9f (200 muM) stimulated currents by 420 ± 33%. Concentration-response studies showed that compound 9c was approximately twice as potent in stimulating GABA currents as alpha-EMTBL (2), the most potent 3,3-dialkylbutyrolactone known to date. On the other hand, the N-sulfonyl analogues were much less active or even inhibited GABA-evoked currents. In vitro radioligand displacement studies on rat brain membranes showed that these compounds did not bind to the benzodiazepine or GABA recognition sites of the GABAA receptor. However, these compounds generally weakly displaced [35S]-TBPS (approximately 50% displacement at 100 muM), though potencies did not correlate with GABA current potentiation. Results obtained with alpha1beta1 and mutant alpha1beta2N265S receptors, which compared to alpha1beta2 receptors are both much less sensitive to current stimulation produced by the anticonvulsant loreclezole, suggest that at least some of these aminobutyrolactones, (e.g., 9a, 9c), and interestingly also alpha-EMTBL, share stimulatory properties with loreclezole.

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

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A substrate-stereocontrolled synthesis of the ABC tricyclic system of daphnicyclidin A is developed. The key reactions include an efficient tandem N-allylation-SN2? reaction to assemble 2,3,4-cis trisubstituent pyrrolidine ring C and two intramolecular Horner-Wadsworth-Emmons reactions to construct cycloheptanone ring A and piperidine ring B.

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Tetrahydrofuran – Wikipedia,
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L-Aspartic acid has been converted to derivatives which undergo alkylation reactions with stereoselectivities that are enantiomerically complimentary.

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Tetrahydrofuran – Wikipedia,
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A four step synthesis of 4(S)-oxazolidineacetic acid, 2-oxo benzyl ester (D-Oxac-OBn) from L-Asp-OH in 45% overall yield is reported. The formation of by-products is completely avoided, by microwave irradiation and by the use of caesium carbonate as base. Moreover the synthesis and IR and 1H NMR conformational analysis of the tetramers Boc-L-Val-D-Oxac-L-Ala-OBn and Boc-L-Val-D-Oxac-Aib-L-Ala-OBn in solution is reported.

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The azido lactone 8 was prepared in a highly stereoselective manner by introduction of an azide function to the lactone 6 derived from L-aspartic acid, and then was converted into (2S,3S)-3-amino-2-azido-4-hydroxybutanoic acid 4. Four-component condensation of the amino acid 4, p-nitrobenzyl isocyanide and formaldehyde or 2,2-diethoxyacetaldehyde furnished the corresponding 3,4-cis-azetidinone 16 or 26 in excellent yield. 3-Methoxy-2-isooxacephalosporin was prepared by the intramolecular acylation of imidazolide 23 derived from compound 16. 3-Unsubstituted 2-isocephem and 2-isooxacephem analogues were prepared from the azetidinone 26.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem