L-(2'S,3'S)-1,6-di-O-benzyl-bis-O-2,3;4,5-(2',3'-dimethoxybutane-2',3'-diyl)-chiro-inositol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: L-(2'S,3'S)-1,6-di-O-benzyl-bis-O-2,3;4,5-(2',3'-dimethoxybutane-2',3'-diyl)-chiro-inositol
• 英文别名: (1S,2S,4S,5S,7R,8R,9R,10R,12S,13S)-4,5,12,13-tetramethoxy-4,5,12,13-tetramethyl-8,9-bis(phenylmethoxy)-3,6,11,14-tetraoxatricyclo[8.4.0.02,7]tetradecane
• 化学式: C₃₂H₄₄O₁₀
• 分子量: 588.695
• InChiKey: URDVKIFSXXHTHP-NTWSACJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  L-(2'S,3'S)-1,6-di-O-benzyl-bis-O-2,3;4,5-(2',3'-dimethoxybutane-2',3'-diyl)-chiro-inositol 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 0.33h， 生成 L-1,6-di-O-benzyl-chiro-inositol
  参考文献：
  名称：

  Synthesis and Biological Activity of d- and l-chiro-Inositol 2,3,4,5-Tetrakisphosphate:  Design of a Novel and Potent Inhibitor of Ins(3,4,5,6)P₄ 1-Kinase/Ins(1,3,4)P₃ 5/6-Kinase

  摘要：

  The synthesis of a novel and potent Ins(3,4,5,6)P-4 1-kinase/Ins(1,3,4)P-3 5/6 kinase inhibitor and its enantiomer is described. D-chiro-Inositol 2,3,4,5-tetrakisphosphate [D-chiro-Ins(2,3,4,5)P-4, 3, Figure 1] and L-chiro-inositol 2,3,4,5-tetrakisphosphate [L-chiro-Ins(2,3,4,5)P-4, ent-3] were synthesized from D-1,6-di-O-benzyl-chiro-inositol and L-1,6-di-O-benzyl-chiro-inositol, respectively. We examined inhibition of the multifunctional Ins(3,4,5,6)P-4 1-kinase/Ins(1,3,4)P-3 5/6kinase from bovine aorta by 3 and ent-3. Compound 3 was a potent inhibitor with an IC50 of 1.5 muM, and ent-3 was more than 20-fold less active. The results are compared to those for other inhibitory inositol polyphosphates with structure-activity relationship discussion. Compound 3 is a useful lead for development of further inhibitors of this important enzyme, and ent-3 should find applications in the newly emerging Ins(1,4,5,6)P-4 signaling pathway.

  DOI：

  10.1021/jm000553k
• 作为产物：
  描述：

  L-chiro-inositol 在 三氟化硼乙醚 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 L-(2'S,3'S)-1,6-di-O-benzyl-bis-O-2,3;4,5-(2',3'-dimethoxybutane-2',3'-diyl)-chiro-inositol
  参考文献：
  名称：

  Synthesis and Biological Activity of d- and l-chiro-Inositol 2,3,4,5-Tetrakisphosphate:  Design of a Novel and Potent Inhibitor of Ins(3,4,5,6)P₄ 1-Kinase/Ins(1,3,4)P₃ 5/6-Kinase

  摘要：

  The synthesis of a novel and potent Ins(3,4,5,6)P-4 1-kinase/Ins(1,3,4)P-3 5/6 kinase inhibitor and its enantiomer is described. D-chiro-Inositol 2,3,4,5-tetrakisphosphate [D-chiro-Ins(2,3,4,5)P-4, 3, Figure 1] and L-chiro-inositol 2,3,4,5-tetrakisphosphate [L-chiro-Ins(2,3,4,5)P-4, ent-3] were synthesized from D-1,6-di-O-benzyl-chiro-inositol and L-1,6-di-O-benzyl-chiro-inositol, respectively. We examined inhibition of the multifunctional Ins(3,4,5,6)P-4 1-kinase/Ins(1,3,4)P-3 5/6kinase from bovine aorta by 3 and ent-3. Compound 3 was a potent inhibitor with an IC50 of 1.5 muM, and ent-3 was more than 20-fold less active. The results are compared to those for other inhibitory inositol polyphosphates with structure-activity relationship discussion. Compound 3 is a useful lead for development of further inhibitors of this important enzyme, and ent-3 should find applications in the newly emerging Ins(1,4,5,6)P-4 signaling pathway.

  DOI：

  10.1021/jm000553k