(+/-)-Araliopsine | 89708-41-8

• 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: (+/-)-Araliopsine
• 英文别名: araliopsine；Araliopsin；2-(2-Hydroxypropan-2-yl)-5-methyl-2,3-dihydrofuro[3,2-c]quinolin-4-one
• CAS: 89708-41-8
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: CHFLECGFLPRCNV-UHFFFAOYSA-N

物化性质

• 沸点：
  391.2±42.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-Araliopsine 在 硫酸 作用下， 反应 0.05h， 生成 2-isopropyl-5-methylfuro<3,2-c>quinolin-4(5H)-one
  参考文献：
  名称：

  Angular Methoxy-Substituted Furo- and Pyranoquinolinones as Blockers of the Voltage-Gated Potassium Channel Kv1.3

  摘要：

  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.

  DOI：

  10.1021/jm001007u
• 作为产物：
  描述：

  5-甲基-4-己烯酸乙酯 在 正丁基锂 、 异丙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 49.42h， 生成 (+/-)-Araliopsine
  参考文献：
  名称：

  Coppola, Gary M., Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 1589 - 1591

  摘要：

  DOI：

文献信息

• Manganese(III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids
  作者：Gregory Bar、Andrew F Parsons、C.Barry Thomas

  DOI：10.1016/s0040-4020(01)00375-1

  日期：2001.5

  mechanism involves an initial intermolecular radical addition reaction followed by radical oxidation and cyclisation steps. Both angular and linear tricyclic alkaloids can be formed and the regioselectivity of the cyclisation is shown to depend on whether alkyl or aryl groups are attached to the alkene.

  三环喹啉生物碱，包括araliopsine 2，可以通过4-羟基-1-甲基-2（1 H）-喹啉5或2,4-喹啉二醇31与乙酸锰（III）在各种富电子烯烃的存在。该反应机理涉及初始的分子间自由基加成反应，然后进行自由基氧化和环化步骤。可以形成有角的和线性的三环生物碱，并且环化的区域选择性显示出取决于烷基或芳基是否连接至烯烃。
• Gaston, John L.; Greer, Robert J.; Grundon, Michael F., Journal of Chemical Research, Miniprint, 1985, # 5, p. 1877 - 1892
  作者：Gaston, John L.、Greer, Robert J.、Grundon, Michael F.

  DOI：——

  日期：——
• A radical approach to araliopsine and related quinoline alkaloids using manganese(III) acetate
  作者：Gregory Bar、Andrew F Parsons、C.Barry Thomas

  DOI：10.1016/s0040-4039(00)01324-1

  日期：2000.9

  Reaction of 4-hydroxy-1-methyl-2(1H)-quinolone 3 with electron-rich alkenes and manganese(III) acetate produces tricyclic quinoline alkaloids, including araliopsine 1, in one-pot reactions. This combined intermolecular addition-cyclisation reaction produces angular and/or linear tricycles and the regioselectivity of the cyclisation is shown to depend on whether alkyl or aryl substituents are attached to the alkene. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Reisch; Iding, Pharmazie, 1993, vol. 48, # 9, p. 696 - 696
  作者：Reisch、Iding

  DOI：——

  日期：——

表征谱图