2-(p-anisoylamino)-5-(β-D-galactopyranosyl)-4-methylthiazole | 1071473-74-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(p-anisoylamino)-5-(β-D-galactopyranosyl)-4-methylthiazole
• 英文别名: 4-methoxy-N-[4-methyl-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1,3-thiazol-2-yl]benzamide
• CAS: 1071473-74-9
• 化学式: C₁₈H₂₂N₂O₇S
• 分子量: 410.448
• InChiKey: HSSUAWJLRUNCMR-GZBLMMOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  170
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-(p-anisoylamino)-5-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4-methylthiazole 在 甲醇 、 sodium methylate 作用下， 以62%的产率得到2-(p-anisoylamino)-5-(β-D-galactopyranosyl)-4-methylthiazole
  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

文献信息

• Synthesis of stable and selective inhibitors of human galectins-1 and -3
  作者：Denis Giguère、Marc-André Bonin、Philipe Cloutier、Ramesh Patnam、Christian St-Pierre、Sachiko Sato、René Roy

  DOI：10.1016/j.bmc.2008.06.044

  日期：2008.8

  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..