4-hydroxy-1H-indole-6-carboxylic acid ethyl ester | 1167056-64-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-hydroxy-1H-indole-6-carboxylic acid ethyl ester
• 英文别名: ethyl 4-hydroxy-1H-indole-6-carboxylate
• CAS: 1167056-64-5
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: WKJZWTBZQAKTBO-UHFFFAOYSA-N

物化性质

• 沸点：
  437.3±25.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-1H-indole-6-carboxylic acid ethyl ester 在 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 7.0h， 生成 6-(Diethoxyphosphorylmethyl)-4-methoxy-3-(3-methylbut-2-enyl)-1-(4-methylphenyl)sulfonylindole
  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-acetoxy-1H-indole-6-carboxylic acid ethyl ester 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以82%的产率得到4-hydroxy-1H-indole-6-carboxylic acid ethyl ester
  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

• [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。
• 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.
• Synthesis and structure activity relationships of schweinfurthin indoles
  作者：John G. Kodet、John A. Beutler、David F. Wiemer

  DOI：10.1016/j.bmc.2014.02.043

  日期：2014.4

  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.