6,7-epoxy-6-methyl-5,8-dioxo-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester | 100374-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6,7-epoxy-6-methyl-5,8-dioxo-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester
• 英文别名: methyl 2-methyl-1,4-naphthoquinone-2,3-epoxide-6-carboxylate；2-Methyl-2,3-epoxy-naphthochinon-(1,4)-carbonsaeure-(6)-methylester
• CAS: 100374-66-1
• 化学式: C₁₃H₁₀O₅
• 分子量: 246.219
• InChiKey: QHNFXEVUGJNMLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.97
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6,7-epoxy-6-methyl-5,8-dioxo-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester 生成 3-Hydroxy-2-methyl-naphthochinon-(1,4)-carbonsaeure-(6)-methylester
  参考文献：
  名称：

  Diquinones—I

  摘要：

  DOI：

  10.1016/s0040-4020(01)97800-7
• 作为产物：
  描述：

  methyl 2-methyl-1,4-naphthoquinone-6-carboxylate 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以72%的产率得到6,7-epoxy-6-methyl-5,8-dioxo-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Epoxides related to dioncoquinone B: Synthesis, activity against multiple myeloma cells, and search for the target protein

  摘要：

  Epoxide 2b is an analog of the synthetic intermediate 2a en route to the polyketide-derived antitumoral naphthoquinone dioncoquinone B (1), isolated from cell cultures of the tropical liana Triphyophyllum peltatum (Dioncophyllaceae). Compound 2b was found to induce strong apoptosis in multiple myeloma cells at a concentration (EC50 = 3.5 mu M), distinctly lower than that of 1 and any related analog, without exerting significant toxicity against normal blood cells. Preliminary studies showed that 2b follows different SAR rules as compared to the naphthoquinones. Among the series of synthesized epoxides, 2b was the most active one and was thus, after biotinylation, subjected to mass spectrometry-based affinity capture experiments aiming at the identification of target proteins. The MS data revealed 2b to address proteins that are associated with stress regulation processes which are critical for multiple myeloma cell survival. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.04.056