5-(β-D-galactopyranosyl)-4-methyl-2-(benzylamino)thiazole | 1071473-66-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(β-D-galactopyranosyl)-4-methyl-2-(benzylamino)thiazole
• CAS: 1071473-66-9
• 化学式: C₁₇H₂₂N₂O₅S
• 分子量: 366.438
• InChiKey: ARDPJJOICGKGBO-GZBLMMOJSA-N

物化性质

• 熔点：
  83-84 °C(Solvent: Ethanol)
• 沸点：
  634.5±65.0 °C(predicted)
• 密度：
  1.463±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为产物：
  描述：

  5-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4-methyl-2-(benzylamino)thiazole 在 甲醇 、 sodium methylate 作用下， 以69%的产率得到5-(β-D-galactopyranosyl)-4-methyl-2-(benzylamino)thiazole
  参考文献：
  名称：

  Synthesis of stable and selective inhibitors of human galectins-1 and -3

  摘要：

  The syntheses of glycolytically stable galactosides and lactosides have been made toward the selective inhibition of human galectins-1 and -3. Transition metal-catalyzed cross-coupling reactions were used to create carbon-carbon bond formation (Sonogashira, Suzuki, Heck, Glaser). Additionally, Hantzsch condensation was used to create novel 2-aminothiazoles which reacted with a panel of acylating and sulfonylating reagents. Moreover, dimeric galactosides and lactosides bearing triazoles, regiospeci.cally prepared using copper-catalyzed Huisgen azide-alkyne [1,3]-dipolar cycloaddition, provided efficient galectins-1 and -3 inhibitors. Best monovalent inhibitor among the tested series was (E)-methyl 2-phenyl-4-(beta-D-galactopyranosyl)-but-2-enoate 15 with inhibitory potency of 313 mu M against galectin-1 and best dimers were bis-lactoside 68 and 75 having both inhibitory properties of 160 mu M against Galectin-3. (c) 2008 Elsevier Ltd. All rights reserved..

  DOI：

  10.1016/j.bmc.2008.06.044