8-Iodo-7-phenylmethoxychromen-2-one | 159979-58-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-Iodo-7-phenylmethoxychromen-2-one
• CAS: 159979-58-5
• 化学式: C₁₆H₁₁IO₃
• 分子量: 378.166
• InChiKey: RVQLEGZQXVEYOA-UHFFFAOYSA-N

物化性质

• 沸点：
  504.591±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.689±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-Iodo-7-phenylmethoxychromen-2-one 在 palladium on activated charcoal palladium diacetate 、 dihydroquinidine 0-O-(9'-phenanthryl) ether 、 K2 、 四丁基溴化铵 、 氢气 、 sodium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 96.0h， 生成 7-Hydroxy-8-((1S,2R)-1,2,3-trihydroxy-3-methyl-butyl)-chromen-2-one
  参考文献：
  名称：

  Reisch, Johannes; Voerste, Arnd A. W., Journal of the Chemical Society. Perkin transactions I, 1994, # 21, p. 3251 - 3256

  摘要：

  DOI：
• 作为产物：
  描述：

  7-羟基香豆素 在 ammonium hydroxide 、 碘 、 sodium hydride 、 potassium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.92h， 生成 8-Iodo-7-phenylmethoxychromen-2-one
  参考文献：
  名称：

  Pancreatic anticancer activity of a novel geranylgeranylated coumarin derivative

  摘要：

  A series of hydroxycoumarin derivatives has been synthesized and evaluated against human pancreatic PANC-1 cancer cells under nutrient-deprived conditions. Several compounds exhibited 100% preferential cytotoxicity at low micromolar concentrations under nutrition starvation, and showed no cytotoxicity under nutrient-rich conditions. In this study, a novel geranylgeranylated ether coumarin derivative 9 was found to exhibit the highest cytotoxic activity of 6.25 mu M within 24 h. The preferential anti-tumor activity exhibited by compound 9 against PANC-1 under low oxygen and nutrient environment illustrates its great potential as a promising lead structure for the development of novel agents to combat pancreatic cancer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.005

文献信息

• Reisch, Johannes; Voerste, Arnd A. W., Journal of the Chemical Society. Perkin transactions I, 1994, # 21, p. 3251 - 3256
  作者：Reisch, Johannes、Voerste, Arnd A. W.

  DOI：——

  日期：——
• Pancreatic anticancer activity of a novel geranylgeranylated coumarin derivative
  作者：Tehsina Devji、Claire Reddy、Christina Woo、Suresh Awale、Shigetoshi Kadota、Dora Carrico-Moniz

  DOI：10.1016/j.bmcl.2011.08.005

  日期：2011.10

  A series of hydroxycoumarin derivatives has been synthesized and evaluated against human pancreatic PANC-1 cancer cells under nutrient-deprived conditions. Several compounds exhibited 100% preferential cytotoxicity at low micromolar concentrations under nutrition starvation, and showed no cytotoxicity under nutrient-rich conditions. In this study, a novel geranylgeranylated ether coumarin derivative 9 was found to exhibit the highest cytotoxic activity of 6.25 mu M within 24 h. The preferential anti-tumor activity exhibited by compound 9 against PANC-1 under low oxygen and nutrient environment illustrates its great potential as a promising lead structure for the development of novel agents to combat pancreatic cancer. (C) 2011 Elsevier Ltd. All rights reserved.