135214-83-4Relevant articles and documents
GLYCOMIMETIC INHIBITORS OF SIGLEC-8
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Page/Page column title page; 14; 3/3, (2008/06/13)
Compounds, compositions and methods are provided for detecting or modulating in vitro and in vivo processes mediated by Siglec-8 binding. More specifically, Siglec-8 modulators and their use are described, wherein the Siglec-8 modulators that modulate a S
Synthesis of the JK/LM-ring model of prymnesins, potent hemolytic and ichthyotoxic polycyclic ethers isolated from the red tide alga Prymnesium parvum: confirmation of the relative configuration of the K/L-ring juncture
Sasaki, Makoto,Takeda, Naoki,Fuwa, Haruhiko,Watanabe, Ryuichi,Satake, Masayuki,Oshima, Yasukatsu
, p. 5687 - 5691 (2007/10/03)
Synthesis of the JK/LM-ring model of prymnesins, polycyclic ether toxins isolated from the red tide phytoflagellate, Prymnesium parvum, is described. Comparison of the 1H and 13C NMR data of the synthetic model with those reported fo
Identifying specific conformations by using a carbohydrate scaffold: Discovery of subtype-selective LPA-receptor agonists and an antagonist
Tamaruya, Yoko,Suzuki, Masato,Kamura, Goshu,Kanai, Motomu,Hama, Kotaro,Shimizu, Kumiko,Aoki, Junken,Arai, Hiroyuki,Shibasaki, Masakatsu
, p. 2834 - 2837 (2007/10/03)
Stable and potent subtype-selective lysophosphatidic acid (LPA) analogues (agonists and an antagonist) were developed by using carbohydrates as a core structure (see scheme). An array of molecules with the recognition motifs of LPA (a phosphate anion, an oleoyl group, and a hydrogen-bond acceptor) attached to carbohydrate isomers in different three-dimensional arrangements were tested for LPA-receptor activation or inhibition. R = alkyl.
Practical synthesis of chiral ligands for catalytic enantioselective cyanosilylation of ketones
Masumoto, Shuji,Yabu, Kazuo,Kanai, Motomu,Shibasaki, Masakatsu
, p. 2919 - 2922 (2007/10/03)
A practical and more environmentally benign synthetic route of chiral ligands that are useful for catalytic enantioselective cyanosilylation of ketones is described. A key step is the regioselective SN2 reaction to cyclic sulfate 12 with catech
Synthesis and Biological Evaluation of a Potent E-Selectin Antagonist
Thonia, Gebhard,Kinzy, Willy,Bruns, Christian,Patton, John T.,Magnani, John L.,Baenteli, Rolf
, p. 4909 - 4913 (2007/10/03)
An early step of the inflammatory response - the rolling of leukocytes on activated endothelial cells - is mediated by selectin/carbohydrate interactions. The tetrasaccharide sialyl Lewisx (sLex) 1 is a ligand for E-, P-, and L-selectin and, therefore, serves as a lead structure to develop analogues which allow the control of acute and chronic inflammation. Here we describe the efficient synthesis (10 linear steps) of the potent sLex mimetic 2. Compared to sLex, compound 2 showed a 30-fold improved affinity in a static, cell-free E-selectin-ligand binding assay (IC50 = 36 μM). These data were confirmed by a marked inhibition in an in vitro cell-cell rolling assay which simulates in vivo conditions (IC50 ca. 40 μM). The assays are predictive for the in vivo efficacy of test compounds as indicated by a marked inhibitory effect of 2 in a thioglycollate induced peritonitis model of acute inflammation in mice (ED50 ca. 15 mg/kg).
Diastereofacial Selectivity of Diels-Alder Reactions of Carbohydrate-Derived Dienes and Their Carbocyclic Analogs
Giuliano, Robert M.,Jordan, Alfonzo D.,Gauthier, A. Diane,Hoogsteen, Karst
, p. 4979 - 4988 (2007/10/02)
The Diels-Alder reactions of two dienes derived from carbohydrates and their carbocyclic analogs are described.The dienes (2S)-3,4-dihydro-2-methoxy-6-vinyl-2H-pyran (1) and (4R)-3,4-dihydro-4-methoxy-6-vinyl-2H-pyran (2) were synthesized from tri-O-acety