(6-benzyloxy-1H-indol-3-yl)acetic acid methyl ester | 183007-38-7

• 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: (6-benzyloxy-1H-indol-3-yl)acetic acid methyl ester
• 英文别名: methyl 2-(6-phenylmethoxy-1H-indol-3-yl)acetate
• CAS: 183007-38-7
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: VDBITBHKKJWCMW-UHFFFAOYSA-N

物化性质

• 沸点：
  480.8±35.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6-benzyloxy-1H-indol-3-yl)acetic acid methyl ester 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 sodium azide 、 氢气 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-羟基吲哚乙胺
  参考文献：
  名称：

  轻松合成6-羟基吲哚-3-乙酸：nephilatoxin-1〜6芳香亚基的结构

  摘要：

  描述了一种容易合成的6-羟基吲哚-3-乙酸1a，它是NPTX-1〜6的拟议芳香亚基。异腈2的自由基环化成功获得了9的高收率。通过1 H-NMR谱图与真实的4-羟基和6-羟基吲哚-3-乙酸的光谱比较，确认NPTX-1〜6的芳族亚基为4-羟基吲哚-3-乙酸12。

  DOI：

  10.1016/0040-4039(96)01583-3
• 作为产物：
  描述：

  4-碘-3-硝基苯酚 在 吡啶 、 盐酸 、 palladium diacetate 、 偶氮二异丁腈 、 三光气 、 (Tol)3P 、 三正丁基氢锡 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 生成 (6-benzyloxy-1H-indol-3-yl)acetic acid methyl ester
  参考文献：
  名称：

  轻松合成6-羟基吲哚-3-乙酸：nephilatoxin-1〜6芳香亚基的结构

  摘要：

  描述了一种容易合成的6-羟基吲哚-3-乙酸1a，它是NPTX-1〜6的拟议芳香亚基。异腈2的自由基环化成功获得了9的高收率。通过1 H-NMR谱图与真实的4-羟基和6-羟基吲哚-3-乙酸的光谱比较，确认NPTX-1〜6的芳族亚基为4-羟基吲哚-3-乙酸12。

  DOI：

  10.1016/0040-4039(96)01583-3

文献信息

• [EN] LIGANDS FOR THE PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR, AND METHODS OF USE THEREOF<br/>[FR] LIGANDS DU RECEPTEUR ACTIVE DE LA PROLIFERATION DES PEROXISOMES ET SES METHODES D'UTILISATION
  申请人：UNIV GEORGETOWN

  公开号：WO2004024939A2

  公开（公告）日：2004-03-25

  One aspect of the present invention relates to compounds that are active at a peroxisome proliferator-activated receptor (PPAR). In certain embodiments, the compound has a isoxazole or indole core. Another aspect of the present invention relates to a method of treating a mammal afflicted with cancer or non-insulin-dependent (type II) diabetes by administering a therapeutic amount of the compounds of the invention. In certain embodiments, the invention relates to a method of treating prostrate, stomach, or breast cancer. Another aspect of the invention relates to a method of identifying ligands active at a PPAR subtype using X-ray structural information. In certain embodiments, the method of identifying the ligand comprises using molecular modeling approaches including: in silico screening of chemical databases, de novo/rational drug design in which the ligand will be created computationally, and/or in silico screening of virtual combinatorial libraries.
• Design and synthesis of alkoxyindolyl-3-acetic acid analogs as peroxisome proliferator-activated receptor-γ/δ agonists
  作者：Hyo Jin Gim、Hua Li、Eun Lee、Jae-Ha Ryu、Raok Jeon

  DOI：10.1016/j.bmcl.2012.11.033

  日期：2013.1

  A series of carbazole or phenoxazine containing alkoxyindole-3-acetic acid analogs were prepared as PPAR gamma/delta agonists and their transactivation activities for PPAR receptor subtypes (alpha, gamma and delta) were investigated. Structure-activity relationship studies disclosed the effect of the lipophilic tail, attaching position of the alkoxy group and N-benzyl substitution at indole. Compound 1b was the most potent for PPARd and 3b for PPAR gamma. Molecular modeling suggested two different binding modes of our alkoxyindole-3-acetic acid analogs providing the insight into their PPAR activity. (C) 2012 Elsevier Ltd. All rights reserved.
• Facile synthesis of 6-hydroxyindole-3-acetic acid: On the structure of the aromatic subunit of nephilatoxin-1∼6
  作者：Tetsuro Shinada、Miki Miyachi、Yasuhiro Itagaki、Hideo Naoki、Kazuo Yoshihara、Terumi Nakajima

  DOI：10.1016/0040-4039(96)01583-3

  日期：1996.9

  A facile synthesis of 6-hydroxyindole-3-acetic acid 1a, which is the proposed aromatic subunit of NPTX-1∼6, is described. Radical cyclization of isonitrile 2 successfully afforded 9 in high yield. The aromatic subunit of NPTX-1∼6 was confirmed as 4-hydroxyindole-3-acetic acid 12 by comparison of the 1H-NMR spectra with those of authentic 4- and 6-hydroxyindole-3-acetic acids.

  描述了一种容易合成的6-羟基吲哚-3-乙酸1a，它是NPTX-1〜6的拟议芳香亚基。异腈2的自由基环化成功获得了9的高收率。通过1 H-NMR谱图与真实的4-羟基和6-羟基吲哚-3-乙酸的光谱比较，确认NPTX-1〜6的芳族亚基为4-羟基吲哚-3-乙酸12。