- A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H
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N-Protected amino acids can be easily converted into chiral α-amino aldehydes in a one-pot reaction by activation with CDI followed by reduction with DIBAL-H. This method delivers Boc-, Cbz- and Fmoc-protected amino aldehydes from proteinogenic amino acids in very good isolated yields and complete stereointegrity.
- Ivkovic, Jakov,Lembacher-Fadum, Christian,Breinbauer, Rolf
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p. 10456 - 10460
(2015/11/10)
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- Resolution and absolute configuration of some a-aminoacetals: En route to enantiopure N-protected a-aminoaldehydes
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The first successful resolution of rac-a-aminoacetals via diastereoisomeric salt formation with optically pure N-protected aminoacids is reported. The absolute configuration assignment of a-aminoacetal enantiomers is performed by an entirely non-racemizing chemical correlation method involving N-protection and a new efficient hydrolysis step followed by a reduction of the resulting N-protected a-aminoaldehyde intermediates. A racemization method of optically enriched a-aminoacetals is exemplified to allow valorisation of both enantiomers. Springer-Verlag 2011.
- Albalat-Serradeil, Muriel,Primazot, Geraldine,Wilhelm, Didier,Vallejos, Jean-Claude,Vanthuyne, Nicolas,Roussel, Christian
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p. 687 - 696
(2012/09/22)
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- IMPROVED AMINOHYDROXYLATION OF ALKENES
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The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.
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Page/Page column 51
(2012/01/06)
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- Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction
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Ethyl-(7), benzyl-(8), tert-butyl-(9), and fluorenylmethyl-4- chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.
- Harris, Lawrence,Mee, Simon P. H.,Furneaux, Richard H.,Gainsford, Graeme J.,Luxenburger, Andreas
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p. 358 - 372
(2011/04/17)
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- Resolution of N-Protected amino alcohols by porcine pancreatic lipase
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The resolution of 2-amino alcohols protected by urethane-type groups either via porcine pancreatic lipase (PPL) hydrolysis of the corresponding racemic acetates or via PPL catalyzed transesterification of racemic alcohols was studied. In both cases, Boc protecting group led to better chemical yields and enantiopurities than Z and Fmoc protecting groups. Furthermore, a simple and efficient method for the synthesis of the medicinally interesting optically pure (R)-2- aminohexadecanol was developed.
- Magrioti, Victoria,Fotakopoulou, Irene,Athinaios, Nicolaos,Anastasopoulou, Panoula,Constantinou-Kokotou, Violetta,Kokotos, George
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scheme or table
p. 159 - 162
(2010/08/19)
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- Carbamate derivatives of felbamate as potential anticonvulsant agents
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Several monocarbamate compounds derived from felbamate were synthesized and 11 target compounds (1, 4, and 6-14) were initially evaluated in mice MES and PTZ models in our laboratory. Carbamate compounds with varying substituents on the oxygen (1-4) gave anticonvulsant activity with a wide range of ED 50 in MES test from 300 mg/kg (4) and compounds with different groups on the nitrogen (5-14) also were quite active in the range of 15 mg/kg (14) to 170.5 mg/kg (6). This suggested that the spatial limitation in the MES model seemed flexible especially on the nitrogen end. All tested compounds showed some activity against mice scPTZ test, but none had the ED50 value 50 mg/kg. Ten selected compounds (1 and 6-14) for subsequent pharmacological evaluation in NIH all gave positive mice MES activity except 8 and 9, which were unexpectedly active in rats after further evaluations. Among the compounds, 1, 8, and 9 advanced to the quantitative study and 1 and 9 provided the highest PI values, 15 and 21, respectively, in the rat oral MES test.
- Kung, Ching-Hsin,Kwon, Chul-Hoon
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experimental part
p. 498 - 513
(2011/03/19)
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- Structure-based design of novel human Pin1 inhibitors (I)
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Pin1 is a member of the cis-trans peptidyl-prolyl isomerase family with potential anti-cancer therapeutic value. Here we report structure-based de novo design and optimization of novel Pin1 inhibitors. Without a viable lead from internal screenings, we de
- Guo, Chuangxing,Hou, Xinjun,Dong, Liming,Dagostino, Eleanor,Greasley, Samantha,Ferre, RoseAnn,Marakovits, Joseph,Johnson, M. Catherine,Matthews, David,Mroczkowski, Barbara,Parge, Hans,VanArsdale, Todd,Popoff, Ian,Piraino, Joseph,Margosiak, Stephen,Thomson, James,Los, Gerrit,Murray, Brion W.
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scheme or table
p. 5613 - 5616
(2010/04/30)
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- Phosphate/sulfate ester compounds and pharmaceutical composition for inhibiting protein interacting NIMA (PIN1)
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Phosphate/sulfate ester compounds that modulate and/or inhibit the activity of protein interacting NIMA (PIN1), and to pharmaceutical compositions containing such compounds are described. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating disorders characterized by hypertension, inappropriate cell proliferation, infectious diseases, and neurodegenerative brain disorders, by administering effective amounts of such compounds.
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Page/Page column 31
(2010/02/14)
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- NOVEL LYSOPHOSPHATIDIC ACID RECEPTOR SELECTIVE ANTAGONISTS
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The present invention is directed to compositions comprising lysophosphatidic acid analogs and methods of using such analogs as agonist or antagonists of LPA receptor activity. In addition the invention is directed to LPA receptor agonists that vary in the degree of selectivity at individual LPA receptors (i.e. LPA1, LPA2 and LPA3). More particularly the present invention is directed to LPA analogs wherein the glycerol is replaced with ethanolamine and a variety of substitutions have been linked at the second carbon atom.
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Page/Page column 75
(2008/06/13)
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- PHOSPHATE/SULFATE ESTER COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS FOR INHIBITING PROTEIN INTERACTING NIMA (PIN1)
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Phosphate/sulfate ester compounds that modulate and/or inhibit the activity of protein interacting NIMA (PIN1), and to pharmaceutical compositions containing such compounds are described. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating disorders characterized by hypertension, inappropriate cell proliferation, infectious diseases, and neurodegenerative brain disorders, by administering effective amounts of such compounds.
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- HYDROXYMORPHOLINONE DERIVATIVE AND MEDICINAL USE THEREOF
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A compound represented by the following formula (I) wherein R1 and R2 are each a lower alkyl group optionally having substituents, which has a calpain inhibitory activity, or a salt thereof is provided.
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- Novel 6-Hydroxy-3-morpholinones as cornea permeable calpain inhibitors
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A novel series of 6-hydroxy-3-morpholinones, in which the functional aldehyde and the hydroxy group of P2 site form a cyclic hemiacetal, was identified as calpain inhibitors. The placement of isobutyl group at the 2-position of the 3-morpholino
- Nakamura, Masayuki,Miyashita, Hiroyuki,Yamaguchi, Masazumi,Shirasaki, Yoshihisa,Nakamura, Yoshikuni,Inoue, Jun
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p. 5449 - 5460
(2007/10/03)
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- New synthetic technology for efficient construction of α-hydroxy-β-amino amides via the passerini reaction
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The Passerini reaction of N-protected amino aldehydes, isonitriles, and TFA using pyridine-type bases proceeds under mild conditions and directly affords α-hydroxy-β-amino amide derivatives in moderate to high yields. These adducts are readily hydrolyzed to αhydroxy-β-amino carboxylic acids. Application of these key intermediates to concise syntheses of P1-α-ketoamide protease inhibitors is illustrated.
- Semple, J. Edward,Owens, Timothy D.,Nguyen, Khanh,Levy, Odile E.
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p. 2769 - 2772
(2007/10/03)
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- Phenylalkylaminoalcohol carbamates and process for preparing the same
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O-carbamoyl-(D/L )-phenylalaninol represented by structural formula I is pharmaceutically useful to treat diseases of the central nervous system, which is prepared by a characteristic process comprising the steps of: treating phenylalaninol with benzyl ch
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- Stereoselective synthesis of 2-amino-1-hydroxy-3-phenylpropylphosphonic acid
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A highly stereoselective synthesis of 2-amino-1-hydroxy-3-phenylpropylphosphonic acid was achieved by simple addition of diethyl phosphite to enantiomeric N-blocked phenylalaninals. These compounds exhibit significant herbicidal activity.
- Zygmunt, Jan,Gancarz, Roman,Lejczak, Barbara,Wieczorek, Piotr,Kafarski, Pawel
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p. 2989 - 2992
(2007/10/03)
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- A facile synthesis of chiral N-protected β-amino alcohols
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Chiral N-protected β-amino alcohols are easily obtained by NaBH4 reduction of mixed anhydrides of N-protected α-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.
- Rodriguez,Llinares,Doulut,Heitz,Martinez
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p. 923 - 926
(2007/10/02)
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- Facile Reduction of Intermediates from Carboxylic Acids and 6-Nitro-1-(2-nitrophenylsulfonyloxy)benzotriazole with Sodium Borohydride to Alcohols
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Reduction of activated intermediates derived from 6-nitro-1-(2-nitrophenylsulfonyloxy)-benzotriazole and carboxylic acids with sodium borohydride readily afforded the corresponding alcohols in 71-93percent yields.Keywords: 6-nitro-1-(2-nitrophenylsulfonyloxy)benzotriazole; 1-acyloxy-6-nitrobenzotriazole; 3-acyl-6-nitrobenzotriazole 1-oxide; sodium borohydride reduction; alcohol synthesis
- Okawara, Tadashi,Ikeda, Norihiro,Yamasaki, Tetsuo,Furukawa, Mitsuru
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p. 3628 - 3631
(2007/10/02)
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