- Enantioselective α-Amination of Acyclic 1,3-Dicarbonyls Catalyzed by N-Heterocyclic Carbene
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Herein, we describe a method for the catalytic enantioselective α-amination of α-substituted acyclic 1,3-ketoamides and 1,3-amidoesters that affords the products possessing N-substituted quaternary stereocenters with a chiral N-heterocyclic carbene (NHC). The reaction is based on the utilization of an intrinsic Br?nsted base characteristic of NHC that enables the catalytic formation of a chiral ion pair comprising the enolate and the azolium ion. A series of challenging open-chain α-substituted 1,3-dicarbonyls are aminated via this method with ee's of ≤99%.
- Santra, Surojit,Maji, Ujjwal,Guin, Joyram
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supporting information
p. 468 - 473
(2020/02/04)
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- Synthesis method of eight-membered ring lactone compounds
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The invention provides a synthesis method of eight-membered ring lactone compounds and belongs to the technical field of medicinal chemistry. The synthesis method comprises steps as follows: firstly, alcohol is dissolved into anhydrous methylene chloride and mixed with acyl chloride for a reaction, and malonic acid compounds are obtained; the malonic acid compounds are dissolved into anhydrous methylene chloride and then is subjected to an olefin cross coupling reaction with allyl acetate, and acetoxyl malonic acid compounds are obtained; finally, under the catalysis of palladium acetate and triphenylphosphine, the acetoxyl malonic acid compounds with the concentration of 0.1 M-0.3 M are subjected to an intramolecular reaction with anhydrous N,N-dimethyl formamide taken as a solvent, and the eight-membered ring lactone compounds are obtained. The synthesis method is simple to operate, a substrate and a catalyst are required to be mixed simply, and the eight-membered ring compounds can be obtained. The synthesis method can be applied to preparation of different products such as products with ester, sulfonyl and methyl in different positions of an eight-membered ring.
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Paragraph 0012
(2017/01/02)
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- Compound for promoting apoptosis of cancer cells, pharmaceutical composition containing the same and uses thereof
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The present invention provides a compound of a formula (I) and a salt thereof, wherein m is an integer of 2 to 7, and R is independently at least one selected from the group consisting of hydrogen and C1-C20 alkyl. The compound promotes apoptosis in cancer cells and inhibits growth of the cancer cells. The present invention also provides a pharmaceutical composition which comprises the compound of the formula (I), a salt thereof and a pharmaceutically acceptable carrier. The present invention further provides uses of the compound of the formula (I) or the salt thereof in preparation of medicine for treating cancer.
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Paragraph 0054; 0055; 0056
(2016/10/09)
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- HIV INTEGRASE INHIBITORS
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The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.
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- trans-directing ability of amide groups in cyclopropanation: Application to the asymmetric cyclopropanation of alkenes with diazo reagents bearing two carboxy groups
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(Chemical Equation Presented) Highly stereoselective: A highly enantioselective (up to 97 % ee) and diastereoselective (>30:1 d.r.) Rh II-catalyzed cyclopropanation of alkenes using a diazo reagent bearing two carboxy groups is described. This new methodology exploits the powerful trans-directing ability of amides to improve enantiocontrol. Mono- and disubstituted olefins are cyclopropanated in good yields. nttl=N-1,8-naphthoyl- tert-leucine.
- Marcoux, David,Charette, Andre B.
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supporting information; experimental part
p. 10155 - 10158
(2009/05/30)
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- Process for the preparation of roquinimex
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The present invention is an improved process to prepare roquinimex (IV) which comprises: (1) contacting N-methyl-N-phenyl-α-carbomethoxyamide (V) with from about one to about two equivalents of base and (2) contacting the mixture of step (1) with N-methylisatoic anhydride (I).
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- Design and synthesis of calcium and magnesium ionophores based on double-armed diazacrown ether compounds and their application to an ion-sensing component for an ion-selective electrode
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The double-armed diazacrown ethers, which have a base diazacrown ether ring with two diamide-type side chains, were designed and synthesized on the basis of the proposed molecular model for the novel neutral Ca2+ and Mg2+ ionophores. The potentiometric ion-selective electrodes were prepared with over 20 kinds of systematically synthesized diazacrown ether derivatives. The relationship between the molecular structures of the ionophores and the ion selectivities was fully discussed. The electrodes based on the 21- and 18-membered diazacrown ether derivatives possessing a glycolic diamide and malonic diamide in their side chains (K23E1 and K22B5) exhibited excellent Ca2+ and Mg2+ selectivities, respectively. The ion-selectivity features of the novel Ca2+ and Mg2+ ionophores supply important structural information about the design of host molecules for alkaline earth metal cations.
- Suzuki, Koji,Watanabe, Kazuhiko,Matsumoto, Yukihiro,Kobayashi, Mitsuru,Sato, Sayaka,Siswanta, Dwi,Hisamoto, Hideaki
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p. 324 - 334
(2007/10/02)
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- Metabolism of the Insecticide Phoxim in Plants and Cell Suspension Cultures of Soybean
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The metabolism of phoxim (Z-α-imino>phenylacetonitrile), Volaton, was investigated using heterotrophic cell suspension cultures of soybean (Glycine max L.) and isolated organs (roots, stems, cotyledons, and leaves) of aseptically grown soybean plants.In both systems phoxim was first hydrolyzed to the corresponding oxime, which was then reduced to a primary nitrile amine.The primary amino group was N-malonylated as the terminal step of the catabolic sequence.The structure of this terminal metabolite was elucidated by spectroscopic (UV, IR, NMR, and MS) methods and chemical synthesis.In the plant no organ-specific differences in phoxim metabolism were observed.In the cell culture system phoxim was quantitatively converted to the N-malonate within 18-20 h, whereas in plant organs such extensive conversion could not be observed even within incubation times of about 5 days.The N-malonate was found to be excreted from the cultured cells into the medium; this effect could not be shown for the plant tissues.Keywords: Organothiophosphate metabolism; soybean plants and cell suspension cultures; conjugation reactions; N-malonylation; O-glucoside formation
- Hoehl, Hans-Ulrich,Barz, Wolfgang
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p. 1052 - 1056
(2007/10/02)
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- Single electron transfer induced elemental steps in the transformation of iodomalonic esters and related CH-acids under solid-liquid PTC conditions. Preparation of electrophilic cyclopropanes
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Single electron transfer induced elemental steps have been shown to occur during the transformation of iodomalonic esters and related CH-acids to cyclopropane derivatives under solid-liquid phase transfer catalytic conditions. The iodo derivatives are formed from iodine and CH-acids "in situ", in the same pot in which the transformations to cyclopropane derivatives take place. A number of electrophilic cyclopropanes with a wide range of substituents have been synthetised by this route.
- Toke, Laszlo,Hell, Zoltan,Szabo, Gabor T.,Toth, Gabor,Bihari, Maria,Rockenbauer, Antal
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p. 5133 - 5146
(2007/10/02)
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- THE SYNTHESIS OFβ-LACTONES AND β-LACTAMS FROM MALONATES AND MALONAMIDES
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The rhodium diacetate induced insertion reactions of some simple esters and amides of diazomalonic acid result in the formation of β-lactones and β-lactams.
- Box, Vernon G. S.,Marinovic, Nash,Yiannikouros, George P.
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p. 245 - 251
(2007/10/02)
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- Heterocyclic aminoalkyl esters of mycophenolic acid, derivatives thereof and pharmaceutical compositions
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Heterocyclic aminoalkyl esters of mycophenolic acid, and the derivatives and pharmaceutically acceptable salts thereof, are useful as immunosuppressive agents, anti-inflammatory agents, anti-tumor agents, anti-viral agents, and anti-psoriatic agents.
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- Studies on antianaphylactic agents. 7. Synthesis of antiallergic 5-oxo-5H-[1]benzopyrano[2,3-b]pyridines
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5-Oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acids 23 and their tetrazole analogues 24 were synthesized from 4-oxo-4H-1-benzopyran-3-carbonitriles or 2-amino-4-oxo-4H-1-benzopyran-3-carboxaldehydes. When administered intravenously, they exhibited antiallergic activity in a reaginic PCA test in rats. In the carboxylic acid series, the activity was influenced by the substituents at the 2-position and increased substantially in the following order: Me, OMe 2 OH, H NHOMe. On the other hand, in the tetrazole series, 2-unsubsitituted derivatives showed the highest activity. Regardless of the kinds of substituents at positions 2 and 3, compounds bearing an alkyl group, especially an isopropyl group at the 7-position, were superior in activity to the corresponding unsubstituted compounds. Among these alkyl derivatives, 3-carboxylic acid derivatives, i.e., 23c (7-ethyl), 23g (2-amino-7-isopropyl), 23r [2-(methoxyamino)-7-isopropyl], and a 3-tetrazole derivative 24c (7-isopropyl), were 41-184 times as potent as disodium cromoglycate. They also exhibited remarkable activity when administered orally; clinical studies on 23g (AA-673) are in progress.
- Nohara,Ishiguro,Ukawa,Sugihara,Maki,Sanno
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p. 559 - 586
(2007/10/02)
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- Ring-expansion of Some Sulfur-containing Heterocyclic Compounds with Dimethyl Acetylenedicarboxylate
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A number of S-heterocyclic, 7-, 8- and 9-membered ring compounds belonging to the benzothiepin, benzothiocin, and benzothionin systems have been prepared through cycloaddition of dimethyl acetylenedicarboxylate to enamines, β-ketoester anions and one β-diketone anion.In the addition to the 5-membered ring compound, 3-hydroxy-2-methoxycarbonylbenzothiophene, a fluorescent by-product has been identified as an α-pyrone besides the main product, a benzothiepin.
- Lamm, Bo,Aurell, Carl-Johan
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p. 435 - 442
(2007/10/02)
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