3-hydroxykhaplofoline | 143704-17-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-hydroxykhaplofoline
• 英文别名: 3-hydroxy-2,2-dimethyl-4,10-dihydro-3H-pyrano[2,3-b]quinolin-5-one
• CAS: 143704-17-0
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: PFODDKQREAWOLH-UHFFFAOYSA-N

物化性质

• 沸点：
  398.8±42.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxykhaplofoline 、 碘甲烷 反应 7.0h， 以90%的产率得到(+/-)-ribalinine
  参考文献：
  名称：

  Subramanian, M.; Mohan, P. S.; Shanmugam, P., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1992, vol. 47, # 7, p. 1016 - 1020

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N'-二(苯基)丙二酰胺 在 sodium hydroxide 、 PPA 、 sodium hydrogen telluride 、 碘 、 silver(I) acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 74.0h， 生成 3-hydroxykhaplofoline
  参考文献：
  名称：

  Subramanian, M.; Mohan, P. S.; Shanmugam, P., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1992, vol. 47, # 7, p. 1016 - 1020

  摘要：

  DOI：

文献信息

• Angular Methoxy-Substituted Furo- and Pyranoquinolinones as Blockers of the Voltage-Gated Potassium Channel Kv1.3
  作者：Inga Butenschön、Kerstin Möller、Wolfram Hänsel

  DOI：10.1021/jm001007u

  日期：2001.4.1

  The voltage-gated potassium channel Kv1.3 constitutes an attractive target for immunosuppression because of its role in T-lymphocyte activation and its functionally restricted expression to lymphocytes. Blockade of Kv1.3 channels by margatoxin has previously been shown to prevent T-cell activation and attenuate immune responses in vivo. In the present study, several furo-and pyranoquinoline derivatives were synthesized add screened for their blocking activities of Kv1.3 channels, stably expressed in mice-fibroblasts L929. In addition the activities of the compounds on Ky currents of the neuroblastoma cell line N1E-115 were determined. The most potent compounds, the angular furoquinolinone 8-methoxy-2-(1 ' -methylethyl)-5-methyl-4,5-dihydrofuro [3,2-c] quinolin-4-one (8c) and the angular pyranoquinolinone 9-methoxy-2,2,6-trimethyl-2,6-dihydro-5H-pyrano [3,2-c] quinolin-5-one (9a), inhibited Kv1.3 channels with half-blocking concentrations of 5 and 10 muM, respectively, and displayed 8-fold (8c) and 2-fold (9a) selectivity over Ky currents of N1E-115 cells. Thus, compounds 8c and 9a might function as a template for the development of novel immunosuppressants.