Chemical Properties and Facts of 2-(3-Bromopropoxy)tetrahydro-2H-pyran

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The synthesis of analogues of the potent acetylcholinesterase inhibitor, Territrem B, was carried out starting from the naturally occurring jujubogenin glycosides. Dihydrojujubogenin-2-en-1-one (1), a dammarane derivative that possesses a skeleton and pharmacophore partially similar to those of Territrem B, was synthesized via three different paths. The derivative 21, which contains two potential pharmacophores, was also synthesized. The anti-AChE activity of the analogues was measured. The aromatic ring moiety seemed to be less important when compared with the 2-en-1-one pharmacophore. (C) 2000 Elsevier Science Ltd.

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A simple, efficient, and mild method for selective bromination of activated aromatic compounds using potassium bromide in the presence of poly(4-vinylpyridine)-supported bromate in nonaqueous solution is reported. The results obtained revealed excellent to good selectiveity between ortho and para positions of methoxyarenes, anilines, and phenols. Copyright Taylor & Francis, Inc.

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A practical protocol for the one-pot synthesis of various aryl sulfonamides, notably of pyridine-core-substituted 7-azaindolyl sulfonamides, is described. A key step is the well-known bromine-lithium exchange reaction of an aryl bromide with tert-butyllithium (t-BuLi). Differing from the common practice to use 2 or more equiv of organolithium, the exact amount of t-BuLi needed for a sufficient exchange reaction is determined for each aryl bromide in a GC-MS-assisted experiment.

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The halogenated aromatic compounds have been important intermediates for various synthetic methods. Electron-rich aromatic compounds were easily iodinated using tetrabutylammonium peroxydisulfate (1) and iodine in mild conditions with excellent yields. Bromination was achieved using 1 and bromine, and regioselective bromination of highly activated aromatic compounds was also achieved using 1 and lithium bromide in mild conditions with excellent yields. Copyright Taylor & Francis Inc.

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The palladium-catalyzed regioselective alpha-monoarylation of deoxybenzoins and alpha,alpha-diarylation of acetophenones provides general, efficient access to 1,2,2-triarylethanones. After a comprehensive search for suitable experimental conditions to optimize such transformations, both reactions are alternatively conducted by means of either commercially available polymer-anchored catalysts or a very simple homogeneous catalytic system, thus avoiding the use of complex ligands. In addition, the synthesis of deoxybenzoins employing polymer-supported fibrous palladium catalysts is reported for the first time, and the excellent catalyst recycling properties suggest applicability to industrial purposes.

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Moist kaolin catalyses the regioselective and high-yielding chlorination and bromination of C6H5OR (R = C1-C8 alkyl. Bu1, allyl, cyclohexyl, benzyl) to 4-XC6H4OR (X = Cl and Br, respectively) with NaCl02 and Mn(acac)3 in CH2Cl2 in the absence and presence of NaBr, respectively, under mild and neutral conditions.

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Treatment of 8-oxabicyclo[3.2.1]oct-6-en-3-one with a catalytic amount of osmium tetraoxide and excess hydrogen peroxide resulted in the formation of the acetonide exo-6,exo-7-isopropylidenedioxy-8-oxabicyclo[3.2.1]oct-3-one (2), in 96% yield. This acetonide was converted into several aromatic alcohols (4a-k) through a Grignard reaction. The alcohols were treated with aqueous HCl in acetone, and the corresponding alkenes (5a-c,e-g,j,k) were obtained in 26-46% overall yield, from the ketone (2). The herbicidal activity of the alkenes was evaluated at a concentra-tion of 6.6 mug g-1. All compounds showed an inhibitory effect (21-66%) on the Sorghum bicolor radicle growth. The inhibition of the accumulation of fresh and dried weight of the aerial parts of Cucumis sativus, after 14 days, varied from 7.1 to 60.7% and from 0.0 to 41.6%, respectively. Compounds (5a,e-g) caused 100% mortality of C. sativus, after 20 days. Compound (5g) (exo-6,exo-7-isopropylidenedioxy-3-(3-methylphenyl)-8-oxabicy-clo[3.2.1]oct-2- ene) was evaluated against several weeds, and it caused 100% mortality of Desmodium tortuosum and Pennisetum setosum.

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This report describes the first results of a rational hit-finding strategy to design novel small molecule antiinflammatory drugs targeting selectins, a family of three cellular adhesion molecules. Based on recent progress in understanding of molecular interaction between selectins and their natural ligands as well as progress in clinical development of synthetic antagonists like 1 (bimosiamose, TBC1269), this study was initiated to discover small molecule selectin antagonists with improved pharmacological properties. Considering 1 as template structure, a ligand-based approach followed by focused chemical synthesis has been applied to yield novel synthetic small molecules (MWr < 500) with a trihydroxybenzene motif, bearing neither peptidic nor glycosidic components, with nanomolar in vitro activity. Biological evaluation involves two kinds of in vitro assays, a static molecular binding assay, and a dynamic HL-60 cell attachment assay. As compared to controls, the novel compounds showed improved biological in vitro activity both under static and dynamic conditions. We very much hope you enjoy reading the articles and that you will join us to present your own research about 33821-94-2, Safety of 2-(3-Bromopropoxy)tetrahydro-2H-pyran

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Nuclear monobromination of aromatic ethers can be achieved with a NaClO2/NaBr/Mn(acac)3 catalyst/silica gel system in dichloromethane in regioselective and high-yielding manner under mild conditions.

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The bromotropolones (4), (5) and (10) undergo palladium-mediated cross coupling with a wide range of organostannanes to produce alkenyl-, alkyl- and aryl-substituted tropolones.The methodology has been applied to the synthesis of the monoterpenes beta-dolabrin (11), beta-thujaplicin (12), 4-isopropyl-7-methoxytropolone (13) and beta-thujaplicinol (14).Cross coupling of bromotropolones (4), (5) and (10) with various aryltrimethylstannanes or arylboronic acids has permitted the preparation of the bicyclic colchicine analogues (30)-(43) which have been tested for tubulin-binding activity.The X-ray crystal structure of the most active of these systems, compound (38), is reported.

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