(2R,4aR,9aR)-5-methoxy-7-[(E)-2-[4-methoxy-3-(3-methylbut-2-enyl)-1-(4-methylphenyl)sulfonylindol-6-yl]ethenyl]-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-2-ol | 1459215-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2R,4aR,9aR)-5-methoxy-7-[(E)-2-[4-methoxy-3-(3-methylbut-2-enyl)-1-(4-methylphenyl)sulfonylindol-6-yl]ethenyl]-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-2-ol
• CAS: 1459215-21-4
• 化学式: C₄₀H₄₇NO₆S
• 分子量: 669.882
• InChiKey: WQHANWSKRDUOND-QHEKFUKSSA-N

物化性质

• 沸点：
  805.9±75.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  48
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  95.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,4aR,9aR)-5-methoxy-7-[(E)-2-[4-methoxy-3-(3-methylbut-2-enyl)-1-(4-methylphenyl)sulfonylindol-6-yl]ethenyl]-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-2-ol 在 sodium hydride 、 异丙醇 作用下， 以 四氢呋喃 为溶剂， 以38%的产率得到(2R,4aR,9aR)-5-methoxy-7-[(E)-2-[4-methoxy-3-(3-methylbut-2-enyl)-1H-indol-6-yl]ethenyl]-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-2-ol
  参考文献：
  名称：

  Synthesis and structure activity relationships of schweinfurthin indoles

  摘要：

  As part of a program to explore the biological activity of analogues of the natural schweinfurthins, a set of compounds has been prepared where an indole system can be viewed as a substitution for the resorcinol substructure of the schweinfurthin's D-ring. Twelve of these schweinfurthin indoles have been prepared and evaluated in the 60 cell line screen of the National Cancer Institute. While a range of activity has been observed, it is now clear that schweinfurthin indoles can demonstrate the intriguing pattern of activity associated with the natural stilbenes. In the best cases, these indole analogues display both potency and differential activity across the various cell lines comparable to the best resorcinol analogues. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.043
• 作为产物：
  描述：

  4-hydroxy-1H-indole-6-carboxylic acid ethyl ester 在 15-冠醚-5 、 四丁基碘化铵 、 zinc trifluoromethanesulfonate 、 sodium hydride 、 potassium carbonate 、 甲基磺酰氯 、 三乙胺 、 N,N-二异丙基乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.75h， 生成 (2R,4aR,9aR)-5-methoxy-7-[(E)-2-[4-methoxy-3-(3-methylbut-2-enyl)-1-(4-methylphenyl)sulfonylindol-6-yl]ethenyl]-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-2-ol 、 (2R,4aR,9aR)-5-methoxy-7-[(E)-2-[4-methoxy-3-(3-methylbut-2-enyl)-1H-indol-6-yl]ethenyl]-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-2-ol
  参考文献：
  名称：

  Synthesis and structure activity relationships of schweinfurthin indoles

  摘要：

  As part of a program to explore the biological activity of analogues of the natural schweinfurthins, a set of compounds has been prepared where an indole system can be viewed as a substitution for the resorcinol substructure of the schweinfurthin's D-ring. Twelve of these schweinfurthin indoles have been prepared and evaluated in the 60 cell line screen of the National Cancer Institute. While a range of activity has been observed, it is now clear that schweinfurthin indoles can demonstrate the intriguing pattern of activity associated with the natural stilbenes. In the best cases, these indole analogues display both potency and differential activity across the various cell lines comparable to the best resorcinol analogues. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.043

文献信息

• SCHWEINFURTHIN ANALOGUES
  申请人：University of Iowa Research Foundation

  公开号：US20150045404A1

  公开（公告）日：2015-02-12

  The invention provides a compound of formula (I): wherein R 1 -R 5 have any of the values defined in the specification. The compounds are useful for the treatment of cancer and other diseases.

  本发明提供了一个化合物的公式(I)：其中R1-R5具有规范中定义的任何值。这些化合物对于治疗癌症和其他疾病是有用的。