- Enantioselective Copper-Catalyzed Radical Ring-Opening Cyanation of Cyclopropanols and Cyclopropanone Acetals
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A novel approach for enantioselective cyanation of cyclopropanols and their derivatives through copper-catalyzed radical relay processes has been developed. Various cyclopropanols and cyclopropanone acetals are compatible to the catalytic conditions, providing β-carbonyl nitriles with excellent enantioselectivity. These products can be readily converted to chiral γ-amino acids derivatives and drugs such as (R)-baclofen. Preliminary mechanistic studies have supported a ring-opening process for cyclopropanoxy radicals followed by copper-catalyzed enantioselective cyanation of benzylic radicals to form the C?CN bonds in an enantioselective manner. (Figure presented.).
- Chen, Pinghong,Guo, Yin-Long,Liu, Guosheng,Wang, Lei,Wu, Lianqian
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supporting information
p. 2189 - 2194
(2020/04/17)
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- Nano-K2CO3: Preparation, characterization and evaluation of reactive activities
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A novel base, nano-K2CO3, was easily prepared by ultrafine wet milling. The surface properties and the reactive activities of nano-K2CO3 were characterized. It was found that such a base showed higher basicity than normal K2CO3 and could replace sodium (or potassium) alkoxide to carry out monoalkylation and oximation of active methylene compounds. The nano-K2CO3 could be regenarated and reused 10 times without loss of its reactive activity.
- Li, Jun-Zhang,Fan, Shi-Ming,Sun, Xuan-Fei,Liu, Shouxin
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p. 1865 - 1869
(2016/01/20)
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- Synthesis and evaluation of 2-phenyl-1,4-butanediamine-based CCR5 antagonists for the treatment of HIV-1
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We describe the synthesis and potency of a novel series of N-substituted 2-phenyl- and 2-methyl-2-phenyl-1,4-diaminobutane- based CCR5 antagonists. Compounds 7a and 12f were found to be potent in anti-HIV assays and bioavailable in the low-dose rat PK model.
- Tallant, Matthew D.,Duan, Maosheng,Freeman, George A.,Ferris, Robert G.,Edelstein, Mark P.,Kazmierski, Wieslaw M.,Wheelan, Pat J.
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scheme or table
p. 1394 - 1398
(2011/04/16)
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- THERAPEUTIC COMPOUNDS
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The present invention relates to compounds of Formula (I) and (Ia) useful in the treatment of CCR5-related diseases and disorders, for example, the prevention or treatment of an HIV infection, and in the treatment of the resulting acquired immune deficien
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Page/Page column 17
(2011/02/24)
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- DERIVATIVES OF 2-PYRIDIN-2-YL-PYRAZOL-3(2H)-ONE, PREPARATION AND THERAPEUTIC USE THEREOF AS HIF ACTIVATORS
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The present invention relates to novel substituted dihydropyrazolone derivatives, to their preparation and to their therapeutic use as activators of the transcription factor HIF.
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Page/Page column 26
(2011/12/13)
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- Synthesis of 3,3-and 4,4-alkyl-phenyl-substituted pyrrolidin-2-one derivatives
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Syntheses of 3,3-and 4,4-alkyl-phenyl-substituted pyrrolidin-2-one derivatives are described. The final compounds were obtained by the reductive cyclization of relevant cyanoalkanoate esters using NaBH4 and CoCl2.6H2O. The obtained pyrroIidin-2-one derivatives are pharmacophoric fragments for the synthesis of various biologically active compounds.
- Kulig,Ignasik,Malawska
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experimental part
p. 1629 - 1636
(2010/07/06)
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- Tetrahydro isoquinoline derivatives, preparation methods and medicinal uses thereof
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A kind of tetrahydro isoquinoline derivatives (I), their preparation methods, medicine compositions and medicinal uses thereof, especially their uses as kappa-opioid receptor excitant in pain relieving, which belongs to the medicine chemistry. The substituents R1, R2, R3, R4 of general formula (I) are defined as the description.
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Page/Page column 6
(2009/12/02)
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- TETRAHYDRO ISOQUINOLINE DERIVATIVES, PREPARATION METHODS AND MEDICINAL USES THEREOF
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A kind of tetrahydro isoquinoline derivatives (I), their preparation methods, medicine compositions and medicinal uses thereof, especially their uses as κ-opioid receptor excitant in pain relieving, which belongs to the medicine chemistry. The substituents R1, R2, R3, R4 of general formula (I) are defined as the description.
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Page/Page column 8
(2009/04/23)
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- A convenient synthesis of 3-arylbutanolides and 3-arylbutenolides
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A series of 3-aryl-substituted butenolides and butanolides has been prepared in a common short synthetic sequence from the corresponding aryl aldehydes. The 3-arylbutanolides are prepared by cyclisation of 3-aryl-3- cyano-1-propanols, obtained by selectiv
- Gu, Jian-Xin,Holland, Herbert L.
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p. 3305 - 3315
(2007/10/03)
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- Inhibition of cyclic adenosine-3',5'-monophosphate phosphodiesterase from vascular smooth muscle by rolipram analogues
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Rolipram [(R,S)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidone] has been shown to inhibit selectively the cAMP phopshodiesterase (PDE) of vascular smooth muscle. In order to further explore the structural requirements for selective PDE inhibition, we synthesized a series of rolipram derivatives differently substituted either at the pyrrolidinone or at the aromatic ring. Among these compounds, rolipram was the most active compound. Semirigid analogues were prepared and used for an evaluation of the active conformation of rolipram. Structural comparison with two other potent and chemically different smooth muscle cAMP-PDE inhibitors, trequinsin and Ro 20-1724, allows us to propose a first topological model of the smooth muscle cAMP-PDE pharmacophore.
- Marivet,Bourguignon,Lugnier,Mann,Stoclet,Wermuth
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p. 1450 - 1457
(2007/10/02)
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- Studies on the Autoxidation of 1-Phenylbuta-1,3-diene and 2-Phenylbuta-1,3-diene
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Hydrogenation of the polymeric peroxides formed during the autoxidation of 1-phenylbuta-1,3-diene (1) and 2-phenylbuta-1,3-diene (10) at 50 deg C in an autoclave yielded 1-phenylbutane-3,4-diol (5) and 2-phenylbutane-1,4-diol(12), respectively.The LiAlH4 reduction of 1-phenylbuta-1,3-diene oxidate (50 deg C) yielded cinnamyl alcohols (4) as a major product.The oxygen-containing polymeric products formed along with Diels-Alder dimers during the oxidation of the title substances at 140 deg C showed no degradation after subjecting to hydrogenation and are therefore considered as polyethers.
- Blau, K.,Voerkel,V.,Willecke, L.
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- PREPARATION AND SOME REACTIONS OF 4- AND 5-ARYL-4,5-DIHYDROPYRIDAZIN-3(2H)-ONES
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Efficient preparations of 4- and 5-phenyl-4,5-dihydropyridazin-3(2H)-ones have been developed, the main reactions of these compounds have been studied, and the synthetic routes have been used to give analogues with substituents in the phenyl rings.In the best synthesis of the 4-phenyldihyropyridazinone (72 percent overall yield) the product was obtained from phenylacetic acid by three simple stages.This approach was applied in preparations of the 2- and 4-hydroxyphenyl compounds and, in conjunction with a recent method for amine protection, the 4-aminophenyl analogue.A four stage synthesis starting from benzaldehyde gave the 5-phenyldihydropyridazinone in 47 percent overall yield; hydroxybenzaldehydes were similarly converted into 5-(allyloxyphenyl)dihydropyridazinones.Oxidation to phenylpyridazinones occured more readily with the 4- and 5-phenyldihydropyridazinones than with the 6-phenyl isomer.The 4- and 5-dihydropyridazinones were smoothly reduced to tetrahydropyridazinones by hydrogenation over platinum but were uneffected by palladium in the presence of hydrazine or cyclohexene.
- Breukelman, Stephen P.,Meakins, G. Denis
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p. 1627 - 1636
(2007/10/02)
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- Organic compounds
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The present invention concerns new heterocyclic compounds of the formula: SPC1 Wherein R1 and R2 are inter alia alkyl, chlorine or methoxy, R3 is hydroxy, alkylcarboxy or monoalkylcarbamoyloxy, and A is protected or unprotected carbonyl. The compounds possess analgesic and central nervous system depressant properties.
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