methyl 2,3,4-tri-O-acetyl-(2'-(4''-methylphenyl)-3'-hydroxy-1'-(E)-propenyloxy)-β-D-glucopyranosiduronate | 676606-06-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-(2'-(4''-methylphenyl)-3'-hydroxy-1'-(E)-propenyloxy)-β-D-glucopyranosiduronate
• CAS: 676606-06-7
• 化学式: C₂₃H₂₈O₁₁
• 分子量: 480.469
• InChiKey: WTRCOXITKUCVPW-FQNWQULGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  143.89
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-(2'-(4''-methylphenyl)-3'-hydroxy-1'-(E)-propenyloxy)-β-D-glucopyranosiduronate 在 4-二甲氨基吡啶 、 barium dihydroxide 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 38.5h， 生成
  参考文献：
  名称：

  A new linker for glucuronylated anticancer prodrugs

  摘要：

  The synthesis, enzymatic hydrolysis and self decomposition of model glucuronylated prodrugs, incorporating a new linker with different aryl substituents, have been studied. Determination of kinetic parameters (V-max, K-m and t(1/2)) showed the important role of aromatic substitution in enzymatic recognition and linker decomposition. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.026
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-(2'-(4''-methylphenyl)-3'-oxo-1'-(E)-propenyloxy)-β-D-glucopyranosiduronate 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以44%的产率得到methyl 2,3,4-tri-O-acetyl-(2'-(4''-methylphenyl)-3'-hydroxy-1'-(E)-propenyloxy)-β-D-glucopyranosiduronate
  参考文献：
  名称：

  A new linker for glucuronylated anticancer prodrugs

  摘要：

  The synthesis, enzymatic hydrolysis and self decomposition of model glucuronylated prodrugs, incorporating a new linker with different aryl substituents, have been studied. Determination of kinetic parameters (V-max, K-m and t(1/2)) showed the important role of aromatic substitution in enzymatic recognition and linker decomposition. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.026

文献信息

• A new spacer group derived from arylmalonaldehydes for glucuronylated prodrugs
  作者：Sébastien Papot、Damien Combaud、Jean-Pierre Gesson

  DOI：10.1016/s0960-894x(98)00454-5

  日期：1998.9

  A new glucuronylated prodrug of doxorubicin, potentially useful for ADEPT or PMT cancer chemotherapy, has been prepared from 4-methyl phenyl malonaldehyde. The enol ether spacer, linked via a carbamate to the 3'-amino group of doxorubicin is rapidly cleaved after beta-glucuronidase (E coli) catalyzed hydrolysis at pH 7.2 and 37 degrees C. (C) 1998 Elsevier Science Ltd. All rights reserved.