3-hydroxy-5-methoxy-1-allyl-1H-indole-2-carboxylic acid ethyl ester | 1315335-86-4

• 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: 3-hydroxy-5-methoxy-1-allyl-1H-indole-2-carboxylic acid ethyl ester
• 英文别名: ethyl 1-allyl-3-hydroxy-5-methoxy-1H-indole-2-carboxylate；Ethyl 3-hydroxy-5-methoxy-1-prop-2-enylindole-2-carboxylate；ethyl 3-hydroxy-5-methoxy-1-prop-2-enylindole-2-carboxylate
• CAS: 1315335-86-4
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: LXZBHNJCZPKMHD-UHFFFAOYSA-N

物化性质

• 沸点：
  416.7±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  60.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙烯酰碘 、 3-hydroxy-5-methoxy-1-allyl-1H-indole-2-carboxylic acid ethyl ester 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 7.0h， 以50%的产率得到1,2-diallyl-5-methoxy-3-oxoindoline-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of a new fluorescent small molecule probe and its use for in vivo lipid imaging

  摘要：

  一种新的小分子探针用于体内脂质成像，LipidGreen（化合物5）被开发出来。LipidGreen能够在3T3L1细胞系中染色脂肪滴，并在斑马鱼中染色脂肪沉积，最高浓度可达100 μM而没有明显的毒性。LipidGreen作为脂肪调节药物筛选平台的功能也在活体斑马鱼中得到了验证。

  DOI：

  10.1039/c1cc11253h
• 作为产物：
  描述：

  3,5-dimethoxy-1H-indole-2-carboxylic acid ethyl ester 在 三溴化硼 、 sodium hydride 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.75h， 生成 3-hydroxy-5-methoxy-1-allyl-1H-indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  An efficient synthesis of LipidGreen and its derivatives via microwave assisted reaction and their live lipid imaging in zebrafish

  摘要：

  We have developed an efficient synthesis of LipidGreen. The conversion is achieved by selective methylation with trimethylsilyldiazomethane, selective deprotection by BBr3 and an improved microwave-assisted C-allylation procedure. Using this route, we have synthesized novel LipidGreen derivatives, and evaluated their live imaging abilities in zebrafish. In this series, Compound 7 is the most active, which is at least 10 fold more potent than LipidGreen. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.090

文献信息

• An efficient synthesis of LipidGreen and its derivatives via microwave assisted reaction and their live lipid imaging in zebrafish
  作者：Haushabhau S. Pagire、Hang-Suk Chun、Myung Ae Bae、Jin Hee Ahn

  DOI：10.1016/j.tet.2013.01.090

  日期：2013.4

  We have developed an efficient synthesis of LipidGreen. The conversion is achieved by selective methylation with trimethylsilyldiazomethane, selective deprotection by BBr3 and an improved microwave-assisted C-allylation procedure. Using this route, we have synthesized novel LipidGreen derivatives, and evaluated their live imaging abilities in zebrafish. In this series, Compound 7 is the most active, which is at least 10 fold more potent than LipidGreen. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of a new fluorescent small molecule probe and its use for in vivo lipid imaging
  作者：Jae Hong Lee、Ju-Hoon So、Jong Hyun Jeon、Eun Bok Choi、Yu-Ri Lee、Young-Tae Chang、Cheol-Hee Kim、Myung Ae Bae、Jin Hee Ahn

  DOI：10.1039/c1cc11253h

  日期：——

  A new small molecule probe for in vivolipid imaging, LipidGreen (compound 5), was developed. LipidGreen stained lipid droplets in 3T3L1 cell lines and fat deposits in zebrafish without apparent toxicity up to 100 μM. The utility of LipidGreen as a drug screening platform for fat regulation was also demonstrated in live zebrafish.

  一种新的小分子探针用于体内脂质成像，LipidGreen（化合物5）被开发出来。LipidGreen能够在3T3L1细胞系中染色脂肪滴，并在斑马鱼中染色脂肪沉积，最高浓度可达100 μM而没有明显的毒性。LipidGreen作为脂肪调节药物筛选平台的功能也在活体斑马鱼中得到了验证。