[4-methoxymethoxy-3-(3-methylbut-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-6-yl]methanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [4-methoxymethoxy-3-(3-methylbut-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-6-yl]methanol
• 化学式: C₂₃H₂₇NO₅S
• 分子量: 429.537
• InChiKey: HJBFTRWVYOADJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  77.76
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [4-methoxymethoxy-3-(3-methylbut-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-6-yl]methanol 在 甲醇 、 15-冠醚-5 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 14.08h， 生成 C₃₂H₃₉NO₄
  参考文献：
  名称：

  [EN] SCHWEINFURTHIN ANALOGUES
  [FR] ANALOGUES DE SCHWEINFURTHINES

  摘要：

  本发明提供一种化合物，其化学式为(I)：其中R1-R5可以是规范中定义的任何值。这些化合物可用于治疗癌症和其他疾病。

  公开号：

  WO2013148584A1
• 作为产物：
  描述：

  4-acetoxy-1H-indole-6-carboxylic acid ethyl ester 在 Tributyl-pentyl-ammoniumiodid 、 zinc trifluoromethanesulfonate 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 、 mineral oil 为溶剂， 反应 5.84h， 生成 [4-methoxymethoxy-3-(3-methylbut-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-6-yl]methanol
  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。
• US9428493B2
  申请人：——

  公开号：US9428493B2

  公开（公告）日：2016-08-30
• Synthesis of Indole Analogues of the Natural Schweinfurthins
  作者：John G. Kodet、David F. Wiemer

  DOI：10.1021/jo4014244

  日期：2013.9.20

  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.
• [EN] SCHWEINFURTHIN ANALOGUES<br/>[FR] ANALOGUES DE SCHWEINFURTHINES
  申请人：UNIV IOWA RES FOUND

  公开号：WO2013148584A1

  公开（公告）日：2013-10-03

  The invention provides a compound of formula (I): wherein R1-R5 have any of the values defined in the specification. The compounds are useful for the treatment of cancer and other diseases.

  本发明提供一种化合物，其化学式为(I)：其中R1-R5可以是规范中定义的任何值。这些化合物可用于治疗癌症和其他疾病。