- Synthesis of sphingosine analogues: Stereoselective synthesis of 3- deoxysphingosine and cis-isomers
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Both enantiomers of 3-deoxysphingosine as well as their cis-isomers were synthesized stereoselectively from L- and D-serine.
- Kawate, Tomohiko,Fukuta, Natsuko,Nishida, Atsushi,Nakagawa, Masako
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- Bifunctional Tripeptide with a Phosphonic Acid as a Br?nsted Acid for Michael Addition: Mechanistic Insights
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Enamine catalysis is a widespread activation mode in the field of organocatalysis and is often encountered in bifunctional organocatalysts. We previously described H-Pro-Pro-pAla-OMe as a bifunctional catalyst for Michael addition between aldehydes and ar
- Cortes-Clerget, Margery,Jover, Jesús,Dussart, Jade,Kolodziej, Emilie,Monteil, Maelle,Migianu-Griffoni, Evelyne,Gager, Olivier,Deschamp, Julia,Lecouvey, Marc
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supporting information
p. 6654 - 6662
(2017/05/15)
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- NOVEL QUINOLINE-SUBSTITUTED COMPOUND
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An object to be achieved by the present invention is to provide a novel compound having EGFR inhibitory effects and cell growth inhibitory effects, as well as a medication useful for the prevention and/or treatment of cancer based on the EGFR inhibitory effects. The present invention provides a compound represented by Formula (I) below, or a salt thereof.
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- Expeditious synthesis of enantiopure, orthogonally protected bis-α-amino acids (OPBAAs) and their use in a study of Nod1 stimulation
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A convenient approach towards the synthesis of orthogonally protected chiral bis-a-amino acids (OPBAAs) is described. The key transformations include: (1) a highly stereoselective conjugation (alkylation) of the Sch?llkopf bislactim ethers and oxazolidinyl alkyl halides to build a backbone skeleton; and (2) our orthogonal protection strategy. A series of enantiopure OPBAAs bearing a variety of alkyl chain as a spacer; two stereogenic centers; and three protecting groups were prepared as examples. These versatile molecules were applied to the synthesis of biologically interesting di- or tri-peptide analogues, including chiral iE-meso-DAP and A-iE-meso-DAP, for the study of Nod1 activation in the innate immune response.
- Chen, Po-Ting,Lin, Cheng-Kun,Tsai, Chih-Ju,Huang, Duen-Yi,Nien, Fu-Yao,Lin, Wan-Wan,Cheng, Wei-Chieh
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p. 474 - 482
(2015/01/30)
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- FACTOR XIa INHIBITORS
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The present invention provides a compound of Formula (I) and pharmaceutical compositions comprising one or more said compounds, and methods for using said compounds for treating or preventing thromboses, embolisms, hypercoagulability or fibrotic changes. The compounds are selective Factor XIa inhibitors or dual inhibitors of Factor XIa and plasma kallikrein.
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- Chemo-enzymatic synthesis of the azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin
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The enzymatic resolution of the N-phenylacetyl derivative of racemic homoserine lactone with penicillin G acylase immobilized on Eupergit C gave (R)-(+)-α-amino-γ-butyrolactone and (S)-(-)-α-N- phenylacetamido-γ-butyrolactone in high enantiomeric purity (ee >99%) and 46-47% yields for each enantiomer. The enantiomers were converted into azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin using Wittig olefination, catalytic ring-closing metathesis (RCM), and stereoselective dihydroxylation with OsO4 in 29% overall yield over 11 high yielding steps. Enzyme inhibition studies showed that 1,4-dideoxyallonojirimycin is a better β-glucosidase inhibitor (IC50 32.4 μM toward β-glucosidase from almonds) and a better β-galactosidase inhibitor (IC50 5.9 mM for β-galactosidase from Aspergillus oryzae) than 1,4-dideoxymannojirimycin (IC50 2.86 mM and 12.5 mM for β-glucosidase and β-galactosidase, respectively).
- Venkataiah, Mallam,Reddipalli, Gowrisankar,Jasti, Lakshmi Swarnalatha,Fadnavis, Nitin W.
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p. 1855 - 1860
(2012/01/13)
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- An asymmetric dihydroxylation route to (-)-bulgecinine
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The stereoselective synthesis of (-)-bulgecinine is reported from L-aspartic acid using Sharpless asymmetric dihydroxylation and intramolecular cyclization via nucleophilic displacement of a-tosylate as key steps.
- Show, Krishanu,Upadhyay, Puspesh K.,Kumar, Pradeep
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experimental part
p. 1234 - 1238
(2011/10/19)
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- PYRROLIDINONE GLUCOKINASE ACTIVATORS
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Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of metabolic diseases and disorders such as, for example, type II diabetes mellitus.
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Page/Page column 73
(2009/10/30)
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- Efficient entry to polysubstituted pyrrolizidines, indolizidines and quinolizidines via a sequential reaction process
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A sequential SN2-Michael addition-Michael addition reaction process between ω-iodo-α,β-alkynoates and δ- or γ-amino α,β-unsaturated esters is developed, which affords polysubstituted pyrrolizidines, indolizidines or quinolizidines in good yield
- Ma, Dawei,Zhu, Wei
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p. 1181 - 1184
(2007/10/03)
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- IMPROVED PROCEDURE FOR THE PREPARATION OF (4S)- OR (4R)-2,2-DIMETHYL-4-(2-HYDROXETHYL)OXAZOLIDINE-3-CARBOXYLIC ACID ALKYL ESTERS
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The present invention is directed to a process for the preparation of (4S)- or (4R)-2,2-dimethyl-4-(2-hydroxethyl)oxazolidine-3-carboxylic acid alkyl esters. The invention is further directed to an intermediate product from which those alkyl esters may be obtained.
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Page/Page column 8; 16
(2010/11/23)
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- Highly efficient approach to orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine
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(Chemical Equation Presented) A concise stereoselective approach to both orthogonally protected (25,4A)- and (2S,4S)-4-hydroxyornithine, key constituents of the biphenomycin-and clavalanine-type antibiotics, respectively, has been developed. The approach is based on bis(oxazoline) copper(II)-complex-catalyzed diastereoselective Henry reactions of nitromethane with the homoserine-derived aldehyde 6. The synthesis of this versatile chiral building block has been markedly improved.
- Paintner, Franz F.,Allmendinger, Lars,Bauschke, Gerd,Klemann, Patricia
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p. 1423 - 1426
(2007/10/03)
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- Stereoselective synthesis of α- and β-L-C-fucosyl aldehydes and their utility in the assembly of C-fucosides of biological relevance
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An efficient synthesis of O-benzylated derivatives of the title sugar aldehydes via thiazole addition to tri-O-benzyl-L-fuconolactone followed by highly stereoselective deoxygenation of the resulting thiazolylketose and thiazole to formyl transformation i
- Dondoni, Alessandro,Catozzi, Nicola,Marra, Alberto
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p. 5023 - 5036
(2007/10/03)
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- Ortho-substituted benzofused macrocyclic lactams as zinc metalloprotease inhibitors
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The design and preparation of ortho-substituted benzofused macrocyclic lactams are described. The benzofused macrocyclic lactams were designed as neutral endopeptidase 24.11 (NEP) inhibitors. Docking studies were carried out in a model of thermolysin (TLN) using the MACROMODEL and QXP modeling programs to select suitable ring sizes. These studies predicted that the 11- , 12-, and 13-membered ring macrocyclic lactams would be active in both enzymes TLN and NEP. Good predictability of experimental results, within this series, of binding to thermolysin and to a lesser extent to NEP was observed. A visual comparison, docked at the active site of TLN, is presented for thiorphan, a 10-membered ring macrocycle and an 11-membered ring benzofused macrocyclic lactam. Potent inhibition of both NEP and thermolysin was obtained. The 11-membered ring macrocycle 25a is the most potent inhibitor from this series of compounds (TLN IC50 = 68 nM; NEP IC50 = 0.9 nM). The effects of prodrug 44b administered at 10 mg/kg po on plasma atrial natriuretic peptide (ANP) levels in conscious rats was greater than 200% over a 4 h period.
- Ksander, Gary M.,De Jesus, Reynalda,Yuan, Andrew,Ghai,Trapani,McMartin, Colin,Bohacek, Regine
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p. 495 - 505
(2007/10/03)
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- Aldehyde derivatives and their use as calpain inhibitors
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Aldehyde derivatives with a specific calpain inhibiting activity and a platelet-aggregation inhibiting effect with formula (I) or formula (II): wherein R1 represents an aromatic hydrocarbon group, a heterocyclic group, or a group of-X-R3 in which X represents O,-S(O)m-(m = 0, 1, or 2), and R3 represents an aromatic hydrocarbon group, a heterocyclic group, or an alkyl group; Z represents R?-Y-or R?O-CH(R?)-in which Y represents a 3-to 7-membered nitrogen-containing saturated heterocyclic group, or a single cyclic saturated hydrocarbon group, R? represents an alkyl group, an alkenyl group, an alkynyl group, an acyl group, a sulfonyl group, an alkoxycarbonyl group, a carbamoyl group, or a thiocarbamoyl group, R? represents hydrogen, an alkyl group, or an aromatic hydrocarbon group, and R? represents an acyl group, a carbamoyl group, a thiocarbamoyl group, or an alkyl group; and n is an integer of 1 to 5. wherein R?, R?, R?, and R1? are defined in the specification.
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