2-(1-methoxynaphthalen-2-yl)-4-methylfuran-3-carboxylic acid | 1159013-13-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-methoxynaphthalen-2-yl)-4-methylfuran-3-carboxylic acid
• CAS: 1159013-13-4
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: ALTYQZBHJIVUTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-(1-methoxynaphthalen-2-yl)-4-methylfuran-3-carboxylic acid 在 氯化亚砜 作用下， 反应 12.0h， 以32%的产率得到methyl 2-(1-methoxynaphthalen-2-yl)-4-methylfuran-3-carboxylate
  参考文献：
  名称：

  Antitumor Agents. 266. Design, Synthesis, and Biological Evaluation of Novel 2-(Furan-2-yl)naphthalen-1-ol Derivatives as Potent and Selective Antibreast Cancer Agents

  摘要：

  In a continuing study, we explored how the individual rings in neo-tanshinlactone (1) influence its potent and selective in vitro antibreast cancer activity. Accordingly, we discovered a novel class of antibreast cancer agents, 2-(furan-2-yl)naphthalen-1-ol derivatives, based on an active C-ring opened model compound S. Further optimization led to 18 and 21, which showed decreased cytotoxic potency but better selectivity than neo-tanshinlactone analogue 2. Interestingly, 20 showed broad cytotoxicity against human cancer cell lines.

  DOI：

  10.1021/jm9001567
• 作为产物：
  描述：

  4-ethyl neo-tanshinlactone 、 碘甲烷 在 potassium hydroxide 、 18-冠醚-6 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 27.5h， 以46%的产率得到2-(1-methoxynaphthalen-2-yl)-4-methylfuran-3-carboxylic acid
  参考文献：
  名称：

  Antitumor Agents. 266. Design, Synthesis, and Biological Evaluation of Novel 2-(Furan-2-yl)naphthalen-1-ol Derivatives as Potent and Selective Antibreast Cancer Agents

  摘要：

  In a continuing study, we explored how the individual rings in neo-tanshinlactone (1) influence its potent and selective in vitro antibreast cancer activity. Accordingly, we discovered a novel class of antibreast cancer agents, 2-(furan-2-yl)naphthalen-1-ol derivatives, based on an active C-ring opened model compound S. Further optimization led to 18 and 21, which showed decreased cytotoxic potency but better selectivity than neo-tanshinlactone analogue 2. Interestingly, 20 showed broad cytotoxicity against human cancer cell lines.

  DOI：

  10.1021/jm9001567

文献信息

• Antitumor Agents. 266. Design, Synthesis, and Biological Evaluation of Novel 2-(Furan-2-yl)naphthalen-1-ol Derivatives as Potent and Selective Antibreast Cancer Agents
  作者：Yizhou Dong、Qian Shi、Yi-Nan Liu、Xiang Wang、Kenneth F. Bastow、Kuo-Hsiung Lee

  DOI：10.1021/jm9001567

  日期：2009.6.11

  In a continuing study, we explored how the individual rings in neo-tanshinlactone (1) influence its potent and selective in vitro antibreast cancer activity. Accordingly, we discovered a novel class of antibreast cancer agents, 2-(furan-2-yl)naphthalen-1-ol derivatives, based on an active C-ring opened model compound S. Further optimization led to 18 and 21, which showed decreased cytotoxic potency but better selectivity than neo-tanshinlactone analogue 2. Interestingly, 20 showed broad cytotoxicity against human cancer cell lines.