5-(benzyloxy)-2-(carboxymethyl)-4-methoxybenzoic acid | 96112-44-6

• 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: 5-(benzyloxy)-2-(carboxymethyl)-4-methoxybenzoic acid
• 英文别名: 4-Benzyloxy-2-carboxy-5-methoxy-phenylessigsaeure
• CAS: 96112-44-6
• 化学式: C₁₇H₁₆O₆
• 分子量: 316.31
• InChiKey: JQQLLHOQFYJJAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-(benzyloxy)-2-(carboxymethyl)-4-methoxybenzoic acid 在 lithium aluminium tetrahydride 作用下， 生成 4-Benzyloxy-2-hydroxymethyl-5-methoxy-phenaethylalkohol
  参考文献：
  名称：

  Prasad,D.; Chaudhury,D.N., Journal of the Indian Chemical Society, 1962, vol. 39, # 10, p. 672 - 676

  摘要：

  DOI：
• 作为产物：
  描述：

  高香草酸 在 盐酸 、 potassium permanganate 、 水 、 potassium carbonate 、 溶剂黄146 、 potassium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 29.5h， 生成 5-(benzyloxy)-2-(carboxymethyl)-4-methoxybenzoic acid
  参考文献：
  名称：

  Identification, Synthesis, and Biological Evaluation of Metabolites of the Experimental Cancer Treatment Drugs Indotecan (LMP400) and Indimitecan (LMP776) and Investigation of Isomerically Hydroxylated Indenoisoquinoline Analogues as Topoisomerase I Poisons

  摘要：

  Hydroxylated analogues of the anticancer topoisomerase I (Top1) inhibitors indotecan (LMP400) and indimitecan (LMP776) have been prepared because (1) a variety of potent Top1 poisons are known that contain strategically placed hydroxyl groups, which provides a clear rationale for incorporating them in the present case, and (2) the hydroxylated compounds could conceivably serve as synthetic standards for the identification of metabolites. Indeed, incubating LMP400 and LMP776 with human liver microsomes resulted in two major metabolites of each drug, which had HPLC retention times and mass fragmentation patterns identical to those of the synthetic standards. The hydroxylated indotecan and indimitecan metabolites and analogues were tested as Top1 poisons and for antiproliferative activity in a variety of human cancer cell cultures and in general were found to be very potent. Differences in activity resulting from the placement of the hydroxyl group are explained by molecular modeling analyses.

  DOI：

  10.1021/jm300519w