- Phosphine-Catalyzed Synthesis of Chiral N-Heterocycles through (Asymmetric) P(III)/P(V) Redox Cycling
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Phosphine-catalyzed tandem Michael addition/intramolecular Wittig reactions have been developed for the synthesis of chiral 2,5-dihydro-1H-pyrrole and tetrahydropyridine derivatives. These processes have been rendered catalytic in phosphine, thanks to the in situ reduction of phosphine oxide by phenylsilane. Furthermore, catalytic and asymmetric P(III)/P(V) processes were implemented using enantiopure chiral phosphines.
- Lorton, Charlotte,Saleh, Nidal,Voituriez, Arnaud
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supporting information
p. 3340 - 3344
(2021/06/26)
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- Oxidative Deprotection of p-Methoxybenzyl Ethers via Metal-Free Photoredox Catalysis
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An efficient and greener deprotection method for p-methoxybenzyl (PMB) ethers using a metal-free visible light photoredox catalyst and air and ammonium persulfate as the terminal oxidants is presented. Various functional groups and protecting groups were tolerated in the developed method to achieve good to excellent yields in short reaction times. Significantly, the developed method was compatible with PMB ethers derived from primary, secondary, and tertiary alcohols and a gram-scale reaction. Mechanistic studies support a proposed reaction mechanism that involves single electron oxidation of the PMB ether.
- Ahn, Deok Kyun,Kang, Young Woo,Woo, Sang Kook
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p. 3612 - 3623
(2019/03/11)
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- For the treatment of tumor macrocyclic derivatives (by machine translation)
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The invention discloses a method for modulating protein kinase activity, and is used for the treatment or prevention of protein kinase related disorders. Specifically, the invention relates to a method for the treatment of tumor of the macrocyclic derivatives, which belongs to the regulating Anaplastic lymphoma kinase (ALK) active compound, and provides the preparation method of the compound, and the compound used for the treatment or prevention of diseases associated with the ALK pharmaceutical use. (by machine translation)
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Paragraph 0177-0178
(2017/07/20)
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- Ligand-controlled α- And β-arylation of acyclic N-boc amines
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The palladium-catalyzed ligand-controlled arylation of α-zincated acyclic amines, obtained by directed α-lithiation and transmetalation, is described. Whereas PtBu3 gave rise to α-arylated Boc-protected amines, more flexible N-phenylazole-based phosphine ligands induced major β-arylation through migrative cross-coupling. All manner of control: The arylation of α-zincated acyclic Boc-protected amines was selectively performed at the α- or β-position in a ligand-controlled manner. α-Arylation occurs by direct reductive elimination of the α-palladated intermediate whereas β-arylation involves palladium migration along the alkyl chain. Boc=tert-butoxycarbonyl.
- Millet, Anthony,Dailler, David,Larini, Paolo,Baudoin, Olivier
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supporting information
p. 2678 - 2682
(2014/03/21)
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- INTEGRIN ANTAGONIST CONJUGATES FOR TARGETED DELIVERY TO CELLS EXPRESSING ALPHA-V-BETA-3
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The invention relates to compounds of formula (I): wherein R1, R2, and n are defined in the detailed description and claims. In particular, the present invention relates to the compounds of formula (I) for use in the manufacture and delivery of conjugated moieties such as small molecules, peptides, nucleic acids, fluorescent moieties, and polymers which are linked to alpha-V-beta-3 integrin antagonists to target cells expressing alpha-V-beta-3.
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Page/Page column 46
(2013/08/15)
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- Zinc triflate: A mild and efficient catalyst for deprotection of tetrahydropyranyl ethers
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Treatment of tetrahydropyranyl (THP) ethers with zinc triflate in methanol provides a simple and efficient process for deprotection of these ethers and the parent alcohols are obtained in excellent yields.
- Srinivasulu,Satyanarayana,Ravi Kumar
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p. 2419 - 2422
(2014/03/21)
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- Simple and efficient method for deprotection of tetrahydropyranyl ethers by using Silica supported sodium hydrogen sulphate
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Tetrahydropyranyl (THP) ethers have been efficiently and simply deprotected by using Silica supported sodium hydrogen sulphate (NaHSO4-SiO 2) in methanol at room temperature to regenerate the parent alcohols in high yields. Tetrahydropyranyl (THP) ethers have been efficiently and simply deprotected by using silica supported sodium hydrogen sulphate (NaHSO 4-SiO2) in methanol at room temperature to regenerate the parent alcohols in high yields.
- Kumar, K. Ravi,Satyanarayana,Reddy, B. Srinivasa
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experimental part
p. 1189 - 1191
(2012/07/27)
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- Oxidative photoredox catalysis: Mild and selective deprotection of PMB ethers mediated by visible light
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Herein we report an advancement in the application of visible light photoredox catalysts in the oxidation of electron-rich arenes resulting in the selective deprotection of para-methoxybenzyl (PMB) ethers. This method is highlighted by excellent functional group tolerance, protecting group orthogonality, mild reaction conditions and avoidance of stoichiometric redox byproducts.
- Tucker, Joseph W.,Narayanam, Jagan M. R.,Shah, Pinkey S.,Stephenson, Corey R. J.
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p. 5040 - 5042
(2011/06/10)
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- Hydrogenation of N-acylcarbamates and N-acylsulfonamides catalyzed by a bifunctional [Cp*Ru(PN)] complex
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Awakening of the Cp one: the bifunctional complex 1 facilitates the interaction with substrates bearing less electrophilic carbon atoms than ketones, epoxides, and imides. The title reaction was applicable to the reduction of Evans' asymmetric alkylation products to the chiral alcohols along with gtood recovery of the chiral oxazolidinone auxiliary. EWG=electron- withdrawing group.
- Ito, Masato,Koo, Lee Wei,Himizu, Akio,Kobayashi, Chika,Sakaguchi, Ayaka,Ikariya, Takao
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scheme or table
p. 1324 - 1327
(2009/06/30)
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- Preliminary biological evaluations of new thalidomide analogues for multiple sclerosis application
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The present work deals with the synthesis of a new series of thalidomide derivatives for therapeutic applications. These compounds were evaluated in vitro on a human endothelial cell line EA.hy926 for their antiproliferative potential and in vivo on an experimental animal multiple sclerosis model called EAE as angiogenesis inhibitors. The preliminary results obtained on EAE assays seem to validate that anti-angiogenesis compounds could be promising tools for the treatment of MS.
- Contino-Pépin, Christiane,Parat, Audrey,Périno, Sandrine,Lenoir, Christine,Vidal, Michel,Galons, Hervé,Karlik, Stephen,Pucci, Bernard
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scheme or table
p. 878 - 881
(2009/09/06)
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- COMPSITIONS, SYNTHESIS, AND METHODS OF USING QUINOLINE BASED ATYPICAL ANTIPSYCHOTIC AGENTS
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The present invention provides novel quinolinone derivatives which can be advantageously used for treating schizophrenia and related psychoses such as acute manic, bipolar disorder, autistic disorder, and depression.
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Page/Page column 29-30
(2009/01/20)
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- QUINAZOLINE DERIVATIVES AS A MULTIPLEX INHIBITOR AND METHOD FOR THE PREPARATION THEREOF
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The present invention relates to a novel quinazoline derivative and a pharmaceutically acceptable salt thereof as a multiplex inhibitor, a method for the preparation thereof, and a pharmaceutical composition and a therapeutic composition comprising same as an active ingredient. The inventive quinazoline derivative as a multiplex inhibitor can selectively and effectively inhibit diseases caused by the overactivity of a tyrosine kinase.
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Page/Page column 42; 104
(2008/06/13)
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- NOVEL AZALIDE AND AZALACTAM DERIVATIVES AND PROCESS FOR THE PRODUCTION OF THE SAME
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A compound represented by the following general formula (1) or a pharmaceutically acceptable salt thereof, which is useful for a prophylactic and/or therapeutic treatment of a microbial infectious disease. [R1 is hydrogen atom, or a linear C1-6 alkylcarbonyl group; R2 is hydrogen atom, or a C1-6 alkylcarbonyl group; R3 is hydrogen atom, a C1-6 alkyl group, a C1-6 alkylcarbonyl group, a C1-6 alkenyl group, a C2-6 alkenylcarbonyl group, a C2-6 alkynyl group, or an Ar-B- group (Ar represents an aryl group, or a heterocyclic group, and B is a C1-6 alkyl group, a C1-6 alkylcarbonyl group, a C2-6 alkenyl group, a C2-6 alkenylcarbonyl group, or a C2-6 alkynyl group); R5, R6, R7, and R8 represent hydrogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, or an Ar-B'- group (B' is a C1-6 alkyl group, a C2-6 alkenyl group, or a C2-6 alkynyl group); X is oxygen atom, or an -NR4- group (R4 is hydrogen atom, a C1-6 alkyl group, or a C1-6 alkyl group which may be substituted with an Ar group); and R4' is hydrogen atom, or a group represented by the aforementioned formula (a) (R3" and R4" represent hydrogen atom, or a linear or branched C1-6 alkylcarbonyl group)]
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Page/Page column 30
(2010/11/08)
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- 1-Amino 1H-imidazoquinolines
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1-Amino 1H-imidazoquinoline compounds, pharmaceutical compositions containing the compounds, intermediates, and methods of making and methods of use of these compounds as immunomodulators, for modulating cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.
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- Efficient chemoselective deprotection of silyl ethers using catalytic 1-chloroethyl chloroformate in methanol
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Fast and chemoselective desilylation of silyl-protected alcohols was achieved using a catalytic amount of 1-chloroethyl chloroformate in methanol. With a minimal amount of 1-chloroethyl chloroformate as the source for anhydrous HCl, extremely efficient cleavage of silyl ethers of primary and secondary alcohols was accomplished, and chemoselective deprotection of one silyl ether in the presence of another silyl or other acid-labile group was possible through controlling the amount of the chloroformate and reaction time.
- Yeom, Chang-Eun,Kim, Young Jong,Lee, So Young,Shin, Yong Je,Kim, B. Moon
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p. 12227 - 12237
(2007/10/03)
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- Branched peptide linkers
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Conjugates containing a targeting ligand, such as an antibody, a therapeutically active drug and a branched peptide linker. The branched peptide linker contains two or more amino acid moieties that provide an enzyme cleavage site. The number of drugs capable of being bonded to the branched linkers varies by a factor of two for each generation of branching.
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- Pyrrolobenzodiazepines
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Compounds of the formulae Ia and Ib: wherein: A is CH2, or a single bond; R2 is selected from: R, OH, OR, CO2H, CO2R, COH, COR, SO2R, CN; R6, R7 and R9 are independently selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn; and R8 is selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn, where R is as defined above, or the compound is a dimer with each monomer being the same or different and being of formula Ia or Ib, where the R8 groups of the monomers form together a bridge having the formula —X—R′—X— linking the monomers, where R′ is an alkylene chain containing from 3 to 12 carbon atoms, which chain may be interrupted by one or more hetero-atoms and/or aromatic rings and may contain one or more carbon-carbon double or triple bonds, and each X is independently selected from O, S, or N; except that in a compound of formula Ia when A is a single bond, then R2 is not CH═CH(CONH2) or CH═CH(CONMe2). Other related compounds are also disclosed.
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- Palladium-catalyzed formation and stereoselective isomerization of 5- vinyloxazolines. Application to the formal synthesis of (S,S)-4-amino-3- hydroxy-5-phenylpentanoic acid
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Vinyloxazolidinones have been found to undergo Pd(0)-catalyzed ionization followed by loss of carbon dioxide and subsequent cyclization to form vinyloxazolines. The reaction occurred under mild conditions, and enhancement of diastereomeric ratios with chiral substrates was obtained. 4- Benzyl-5-vinyloxazoline prepared by this method has been utilized in the stereoselective synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA).
- Cook,Shanker
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p. 3405 - 3408
(2007/10/03)
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- N-t-butoxycarbonyl protection of primary and secondary amines in the hydroboration reaction: Synthesis of amino alcohols
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The use of the BOC group as a protecting group in the hydroboration of aminoalkenes is described. The isolated yields of amino alcohols via the hydroboration-oxidation sequence are excellent.
- Kabalka,Li,Pace
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p. 2135 - 2143
(2007/10/02)
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- Acylated amine compounds which are useful fungicigal agents
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A compound selected from the group consisting of a compound of the formula STR1 wherein R1 is selected from the group consisting of Ar-O- and aryl, polyaryl and condensed polyaryl unsubstituted or substituted and heterocycle unsubstituted or substituted, Ar is aryl of 6 to 14 carbon atoms unsubstituted or substituted, heteroaryl unsubstituted or substituted and heterocyclic unsubstituted or substituted, W is selected from the group comsisting of --(CH2)n1 --or --(CH2)n2 --NY--(CH2)n3, n1, n2 and n3 are individually integers from 2 to 6, Y is selected from the group consisting of hydrogen, alkyl of 1 to 12 carbon atoms, aryl of 6 to 12 carbon atoms and aralkyl of 7 to 14 carbon atoms unsubstituted or substituted, --COOAlk and --COR2, Alk is alkyl of 1 to 12 carbon atoms, R2 is selected from the group consisting of alkyl of 1 to 12 carbon atoms, alkenyl and alkynyl of 2 to 12 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms unsubstituted or substituted and heterocyclic unsubstituted or substituted, Z is selected from the group consisting of hydrogen, STR2 R2 is alkyl of 1 to 12 carbon atoms or aralkyl of 7 to 18 carbon atoms, Alk' is alkyl of 1 to 12 carbon atoms, ArAlk is aralkyl of 7 to 18 carbon atoms, R2 ' is R2, R3 and R3 ' are selected from the group consisting of aryl substituted or unsubstituted, heteroaryl substituted or unsubstituted, heterocyclic unsubstituted or substituted and R1 with the proviso that Z is not hydrogen when W is --(CH2)3 --and R1 is 2,4-dichlorophenoxy and their non-toxic, pharmaceutically acceptable acid addition salts having fungicidal activity.
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- Cyclic amidinyl and cyclic guanidinyl thio carbapenems
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Compounds of the formula: STR1 and the pharmaceutically acceptable salts thereof wherein X is STR2 wherein each R is hydrogen or alkyl of 1 to 6 carbon atoms are disclosed. The compounds are useful as antibiotics.
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- MILD AND SELECTIVE RING-CLEAVAGE OF CYCLIC CARBAMATES TO AMINO ALCOHOLS
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N-tert-Butoxycarbonylated 2-oxazolidinones and tetrahydro-2-oxazinones are smoothly cleaved to acyclic N-Boc-amino alcohols on treatment with catalytic amounts of cesium carbonate at room temperature.The versatility of the procedure is demonstrated in a facile cleavage of highly functionalized heterocycles without epimerization and β-elimination.
- Ishizuka, Tadao,Kunieda, Takehisa
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p. 4185 - 4188
(2007/10/02)
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