4-methoxybenzyl 2-oxocyclohexanecarboxylate | 111948-89-1

• 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: 4-methoxybenzyl 2-oxocyclohexanecarboxylate
• 英文别名: (4-methoxyphenyl)methyl 2-oxocyclohexane-1-carboxylate
• CAS: 111948-89-1
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: RQWNGWCIIWKMMF-UHFFFAOYSA-N

物化性质

• 沸点：
  395.9±37.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-methoxybenzyl 2-oxocyclohexanecarboxylate 在 三氟乙酸 、 三氟乙酸酐 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 (1S,6R,8R,12R)-8-methyl-7,15-dioxatetracyclo[6.5.2.01,6.06,12]pentadecan-14-one
  参考文献：
  名称：

  Regiochemistry of intramolecular photocycloaddition of 1,3-dioxin-4-ones tethered through the ketal carbon

  摘要：

  1,3-Dioxin-4-one photosubstrates were prepared by condensation of alkenones with ketoesters or formyl Meldrum's Acid. The resulting dioxinones contained enone and alkene chromophores, linked through the ketal carbon of the dioxinone ring. The dioxinones were irradiated and the regiochemistry of the photoproducts was established. Substrates with a two carbon tether gave head to head products, while substrates with a three or four carbon tether gave predominantly head to tail products. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10381-1
• 作为产物：
  描述：

  环己酮 、 anisyl cyanoformate 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 生成 4-methoxybenzyl 2-oxocyclohexanecarboxylate
  参考文献：
  名称：

  一种合成二氧杂环戊烯酮与茴香酸氰基甲酸酯羧化酮烯酸酯的新方法

  摘要：

  我们描述的分子内二氧戊烯酮光环加成反应的普遍性取决于所需官能化的二氧杂环戊烯酮的可用性。我们在此报告了通过酮烯酸酯与茴香基氰基甲酸酯的羧化以及所得酮酯与丙酮的缩合来制备二氧杂环戊酮的一般方法。

  DOI：

  10.1016/s0040-4039(00)95908-2

文献信息

• Identification of Fumarate Hydratase Inhibitors with Nutrient-Dependent Cytotoxicity
  作者：Toshifumi Takeuchi、Paul T. Schumacker、Sergey A. Kozmin

  DOI：10.1021/ja5101257

  日期：2015.1.21

  Development of cell-permeable small molecules that target enzymes involved in energy metabolism remains important yet challenging. We describe here the discovery of a new class of compounds with a nutrient-dependent cytotoxicity profile that arises from pharmacological inhibition of fumarate hydratase (also known as fumarase). This finding was enabled by a high-throughput screen of a diverse chemical library in a panel of human cancer cell lines cultured under different growth conditions, followed by subsequent structure-activity optimization and target identification. While the highest cytotoxicity was observed under low glucose concentrations, the antiproliferative activities and inhibition of oxygen consumption rates in cells were distinctly different from those displayed by typical inhibitors of mitochondrial oxidative phosphorylation. The use of a photoaffinity labeling strategy identified fumarate hydratase as the principal pharmacological target. Final biochemical studies confirmed dose-dependent, competitive inhibition of this enzyme in vitro, which was fully consistent with the initially observed growth inhibitory activity. Our work demonstrates how the phenotypic observations combined with a successful target identification strategy can yield a useful class of pharmacological inhibitors of an enzyme involved in the operation of tricarboxylic acid cycle.