1-乙基-1H-吲哚-3-羧酸乙酯 | 885524-96-9

• 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
• 中文名称: 1-乙基-1H-吲哚-3-羧酸乙酯
• 英文名称: 1-Ethyl-1H-indole-3-carboxylic acid ethyl ester
• 英文别名: 1-ethylindole-3-carboxylic acid ethyl ester；ethyl 1-ethylindole-3-carboxylate
• CAS: 885524-96-9
• 化学式: C₁₃H₁₅NO₂
• mdl: MFCD11617126
• 分子量: 217.268
• InChiKey: DKTASPVYNKDYMO-UHFFFAOYSA-N

物化性质

• 沸点：
  345.5±15.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-乙基-1H-吲哚-3-羧酸乙酯 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 水 、 cesium acetate 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 9-ethyl-3-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)-4-phenyl-2,9-dihydro-1H-pyrido[3,4-b]indol-1-one
  参考文献：
  名称：

  抑制AKT/mTOR信号通路的β-咔啉类天然产物的设计、合成及其抗癌活性

  摘要：

  非小细胞肺癌（NSCLC）是最常见的肺癌类型，并且仍然是癌症死亡的主要原因。 NSCLC 的治疗已取得很大进展，然而，只有有限的患者可以从当前的治疗中受益。因此，需要付出更多努力来探索非小细胞肺癌治疗的新分子模式。事实证明，伪天然产物（PNP）是抗肿瘤药物发现的关键来源。在此，我们描述了一种 CH 激活方案，用于利用 PNP 理性设计策略方便地构建重点库。该方案的特点是 -OAc-indole-2-carboxamide 和炔基醌之间发生铑催化的 CH 活化/[4+2] 成环反应，从而能够轻松获得各种喹啉取代的咔啉衍生物（31 个示例）。针对 NSCLC 细胞系 A549 评估抗癌活性，产生有效的抗增殖-咔啉衍生物 ()，IC 值为 0.8 ± 0.1 µM。进一步研究发现，该化合物可以降低Caspase 3的表达，增加自噬蛋白Cyclin B1的表达，从而显着诱导自噬和细胞凋亡。机制研究表明，它可能通过

  DOI：

  10.1016/j.bioorg.2024.107648
• 作为产物：
  描述：

  乙酸乙酯 、 1-ethyl-1H-indole-3-carboxylic acid methyl ester 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 1-乙基-1H-吲哚-3-羧酸乙酯
  参考文献：
  名称：

  Simple, fast and efficient synthesis of β-keto esters from the esters of heteroaryl compounds, its antimicrobial study and cytotoxicity towards various cancer cell lines

  摘要：

  A series of beta-keto esters were synthesized from heteroaryl esters and ethyl acetate using LiHMDS as base at -50 to -30 degrees C. The increase in yields of cross condensed product were observed and the percentage of self condensed product was reduced drastically by applying the suitable base (LiHMDS), solvent and the minimum amount of ethyl acetate. All these beta-keto esters were characterized using H-1 NMR, C-13 NMR and mass spectral data. A plausible mechanism is also depicted to prove the formation of trans-esterified products. All the synthesized compounds were subjected to test for their cytotoxicity towards various cancer cell lines and also tested for their antimicrobial activity towards various bacterial and fungal strains and some of them were found to have promising activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.008

文献信息

• MODULATORS OF ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTORS AND THERAPEUTIC USES THEREOF
  申请人：Ghiron Chiara

  公开号：US20100029606A1

  公开（公告）日：2010-02-04

  The present invention provides compounds of formula (I) and compositions thereof, methods of making them, and methods of using them to modulate alpha7 nicotinic acetylcholine receptors and/or to treat any of a variety of disorders, diseases, and conditions. Provided compounds can affect, among other things, neurological, psychiatric and/or inflammatory system.

  本发明提供了式(I)的化合物及其组合物，制备它们的方法，以及使用它们调节α7尼古丁乙酰胆碱受体和/或治疗各种疾病、疾病和病症的方法。提供的化合物可以影响神经、精神和/或炎症系统等方面。
• Modulators of α7 nicotinic acetylcholine receptors and therapeutic uses thereof
  申请人：Wyeth

  公开号：US08163729B2

  公开（公告）日：2012-04-24

  The present invention provides compounds of formula (I) and compositions thereof, methods of making them, and methods of using them to modulate alpha7 nicotinic acetylcholine receptors and/or to treat any of a variety of disorders, diseases, and conditions. Provided compounds can affect, among other things, neurological, psychiatric and/or inflammatory system.

  本发明提供了式(I)的化合物及其组合物、制备方法和使用它们调节α7尼古丁乙酰胆碱受体和/或治疗各种疾病、疾病和病症的方法。提供的化合物可以影响神经、精神和/或炎症系统等方面。
• US8163729B2
  申请人：——

  公开号：US8163729B2

  公开（公告）日：2012-04-24
• Simple, fast and efficient synthesis of β-keto esters from the esters of heteroaryl compounds, its antimicrobial study and cytotoxicity towards various cancer cell lines
  作者：R. Venkat Ragavan、V. Vijayakumar、K. Rajesh、B. Palakshi Reddy、S. Karthikeyan、N. Suchetha Kumari

  DOI：10.1016/j.bmcl.2012.04.008

  日期：2012.6

  A series of beta-keto esters were synthesized from heteroaryl esters and ethyl acetate using LiHMDS as base at -50 to -30 degrees C. The increase in yields of cross condensed product were observed and the percentage of self condensed product was reduced drastically by applying the suitable base (LiHMDS), solvent and the minimum amount of ethyl acetate. All these beta-keto esters were characterized using H-1 NMR, C-13 NMR and mass spectral data. A plausible mechanism is also depicted to prove the formation of trans-esterified products. All the synthesized compounds were subjected to test for their cytotoxicity towards various cancer cell lines and also tested for their antimicrobial activity towards various bacterial and fungal strains and some of them were found to have promising activity. (C) 2012 Elsevier Ltd. All rights reserved.