ethyl 6-methoxyindole-3-carboxylate | 88612-61-7

• 物质功能分类: 有机原料 - 杂环化合物
• 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: ethyl 6-methoxyindole-3-carboxylate
• 英文别名: Ethyl-6-methoxyindol-3-carboxylat；6-methoxy-indole-3-carboxylic acid ethyl ester；Ethyl 6-methoxy-1H-indole-3-carboxylate
• CAS: 88612-61-7
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: CSIPRHXURLYZMP-UHFFFAOYSA-N

物化性质

• 熔点：
  142.0-142.5 °C(Solv: water, 50% (7732-18-5); ethanol (64-17-5))
• 沸点：
  380.2±22.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  ethyl 6-methoxyindole-3-carboxylate 在 一水合肼 、 乙酰氯 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 5-(6-methoxy-1H-indol-3-yl)-N-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles as potent cytotoxic agents

  摘要：

  A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles 6a-v were prepared and studied for their anticancer activity against selected human cancer cell lines. The reaction of indolylhydrazides 3a-h with a variety of aryl isothiocyanates 4 afforded the key intermediate thiosemicarbazides 5a-v, which upon treatment with acetyl chloride produced the 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles 6a-v in good yields. Most of the synthesized compounds showed selective cytotoxicity towards human breast cancer cell line (MDA-MB-231). Of the synthesized 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles, compound 6f is the most potent towards tested cancer cell lines (IC50 = 0.15-1.18 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.047
• 作为产物：
  描述：

  ethyl (Z)-3-azido-2-(4-methoxyphenyl)prop-2-enoate 生成 ethyl 6-methoxyindole-3-carboxylate
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• A Practical Synthesis of Indole-Based Heterocycles Using an Amidoaluminum-Mediated Strategy
  作者：M. Hossain、Robert Todd

  DOI：10.1055/s-0028-1088071

  日期：2009.6

  A large number of biologically active compounds consist of an indole scaffolding. Because of this, chemists are continually searching for more efficient means through which to successfully synthesize the required alkaloids. In our recent effort to synthesize indole-based p38 inhibitors and gramines, we found that a series of indole-based indole-3-carboxamides could be efficiently synthesized from various indole-3-carboxylates using an amidoaluminum-mediated strategy. The treatment of ethyl indole-3-carboxylates bearing a range of substitution patterns on the indole ring with various amidoaluminum complexes, led to the corresponding 1H-indole-3-carboxamides in yields up to 75%. Reduction by diisobutylaluminum hydride afforded the corresponding gramines in 63-85% yield. This is the first reported example of amidoaluminum complexes of type Al2(CH3)4(NR2)2 promoting facile amidation of relatively inert indole esters. This particularly promising approach has resulted in the first strategy for generating medicinally important alkaloids of this type.

  大量生物活性化合物含有吲哚骨架。因此，化学家们不断寻找更有效的方法来成功合成所需的生物碱。在我们最近努力合成基于吲哚的p38抑制剂和尼亚辛时，我们发现一系列基于吲哚的吲哚-3-羧酰胺可以通过酰胺铝介导的策略从各种吲哚-3-羧酸盐高效合成。用各种酰胺铝复合物处理带有不同取代模式的吲哚环的乙基吲哚-3-羧酸盐，得到了相应的1H-吲哚-3-羧酰胺，收率高达75%。通过二异丁基铝氢还原得到了相应的尼亚辛，收率为63-85%。这是首次报道的类型为Al2(CH3)4(NR2)2的酰胺铝复合物促进相对惰性的吲哚酯的易于酰胺化的例子。这种特别有希望的方法已经产生了一种生成这种类型的具有药用重要性的生物碱的首创策略。
• Palladium-Catalyzed Synthesis of 3-Indolecarboxylic Acid Derivatives
  作者：Björn Söderberg、Serge Banini、Michael Turner、Aaron Minter、Amanda Arrington

  DOI：10.1055/s-2008-1032208

  日期：2008.3

  Indoles having an ester functionality in the 3-position were prepared from 2-(2-nitrophenyl)propenoic acid derivatives via a palladium-catalyzed reductive N-heteroannulation using carbon monoxide as the ultimate reducing agent. The starting materials were prepared either by a Stille coupling of 2-halo-1-nitrobenzenes with ethyl 2-(tributylstannyl)-2-propenoate or by vicarious nucleophilic substitution

  在 3 位具有酯官能团的吲哚是由 2-(2-硝基苯基) 丙烯酸衍生物通过钯催化的还原性 N-杂环化制备的，使用一氧化碳作为最终还原剂。通过 2-卤代-1-硝基苯与 2-(三丁基甲锡烷基)-2-丙烯酸乙酯的 Stille 偶联或通过硝基苯的替代亲核取代然后与醛进行 Knoevenagel 型缩合来制备起始材料。还使用相同类型的方法描述了合成 3-腈和 3-砜取代的吲哚的例子。
• KASAHARA, AKIRA;IZUMI, TAEKO;MURAKAMI, SATOSHI;YANAI, HIROSHI;TAKATORI, M+, BULL. CHEM. SOC. JAP., 1986, 59, N 3, 927-928
  作者：KASAHARA, AKIRA、IZUMI, TAEKO、MURAKAMI, SATOSHI、YANAI, HIROSHI、TAKATORI, M+

  DOI：——

  日期：——
• ——
  作者：TSUNEHMOTO DAJEHJ、 OXORI TAKEHO、 NAGASIMA NAOESI

  DOI：——

  日期：——
• ECTONUCLEOTIDE PYROPHOSPHATASE-PHOSPHODIESTERASE-1 INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  申请人：[en]LEGOCHEM BIOSCIENCES, INC.

  公开号：WO2023242631A1

  公开（公告）日：2023-12-21

  The present disclosure relates compounds for inhibiting ectonucleotide pyrophosphatase/phosphodiesterase-1 (ENPP-1), or a pharmaceutically acceptable salts thereof.