(2R,4aR,9aR)-5-methoxy-7-[(E)-2-[4-(methoxymethoxy)-2-(3-methylbut-2-enyl)-1-(4-methylphenyl)sulfonylindol-6-yl]ethenyl]-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-2-ol | 1453472-33-7

• 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-(methoxymethoxy)-2-(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: 1453472-33-7
• 化学式: C₄₁H₄₉NO₇S
• 分子量: 699.909
• InChiKey: WKTBSFSSUUJJRG-LCKRTDJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  50
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,4aR,9aR)-5-methoxy-7-[(E)-2-[4-(methoxymethoxy)-2-(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 15-冠醚-5 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 mineral oil 为溶剂， 反应 14.0h， 生成 6-[2-(7-hydroxy-4-methoxy-8,8,10a-trimethyl-(5R,8aR,10aR)-5,7,8,8a,9,10a-hexahydro-6H-xanthen-2-yl)-vinyl]-2-(3-methylbut-2-enyl)-1H-indol-4-ol
  参考文献：
  名称：

  Synthesis of Indole Analogues of the Natural Schweinfurthins

  摘要：

  An interest in the schweinfurthins, natural stilbenes with significant antiproliferative activity, has prompted efforts to prepare a set of indole analogues. To approach the desired compounds through a Horner-Wadsworth-Emmons condensation, new indole derivatives bearing a phosphonomethyl substituent in the B-ring were required. The parent indole system with the necessary substitution pattern was obtained through Stobbe condensation and cyclization. A prenyl substituent was incorporated at the C3 position of a 4,6-disubstituted indole through a highly regioselective electrophilic aromatic substitution reaction, while metalation and alkylation provided the C2-prenylated indole. After introduction of the phosphonate group through classical reactions, the new indole phosphonates were found to undergo the desired condensation with nonracemic aldehydes representing the schweinfurthin left half. This approach provides facile access to new heteroaromatic analogues of the natural schweinfurthins and should be applicable to many other natural stilbenes as well.

  DOI：

  10.1021/jo4014244
• 作为产物：
  描述：

  [4-methoxymethoxy-2-(3-methylbut-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-6-yl]methanol 在 15-冠醚-5 、 sodium hydride 、 甲基磺酰氯 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 7.08h， 生成 (2R,4aR,9aR)-5-methoxy-7-[(E)-2-[4-(methoxymethoxy)-2-(3-methylbut-2-enyl)-1-(4-methylphenyl)sulfonylindol-6-yl]ethenyl]-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-2-ol
  参考文献：
  名称：

  Synthesis of Indole Analogues of the Natural Schweinfurthins

  摘要：

  An interest in the schweinfurthins, natural stilbenes with significant antiproliferative activity, has prompted efforts to prepare a set of indole analogues. To approach the desired compounds through a Horner-Wadsworth-Emmons condensation, new indole derivatives bearing a phosphonomethyl substituent in the B-ring were required. The parent indole system with the necessary substitution pattern was obtained through Stobbe condensation and cyclization. A prenyl substituent was incorporated at the C3 position of a 4,6-disubstituted indole through a highly regioselective electrophilic aromatic substitution reaction, while metalation and alkylation provided the C2-prenylated indole. After introduction of the phosphonate group through classical reactions, the new indole phosphonates were found to undergo the desired condensation with nonracemic aldehydes representing the schweinfurthin left half. This approach provides facile access to new heteroaromatic analogues of the natural schweinfurthins and should be applicable to many other natural stilbenes as well.

  DOI：

  10.1021/jo4014244

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。