ethyl 5-bromo-1-methyl-1H-indole-3-carboxylate | 1373147-89-7

• 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: ethyl 5-bromo-1-methyl-1H-indole-3-carboxylate
• 英文别名: 5-bromo-1-methyl-1H-indole-3-carboxylic acid ethyl ester；ethyl 5-bromo-1-methylindole-3-carboxylate
• CAS: 1373147-89-7
• 化学式: C₁₂H₁₂BrNO₂
• 分子量: 282.137
• InChiKey: AMGUQPRHBALGGA-UHFFFAOYSA-N

物化性质

• 沸点：
  384.2±22.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-methyl-N'-(1-(3,4,5-trimethoxyphenyl)ethylidene)benzenesulfonohydrazide 、 ethyl 5-bromo-1-methyl-1H-indole-3-carboxylate 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 、 lithium tert-butoxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以89%的产率得到ethyl 1-methyl-5-(1-(3,4,5-trimetoxyphenyl)vinyl)-1H-indole-3-carboxylate
  参考文献：
  名称：

  Design and Synthesis of Tubulin and Histone Deacetylase Inhibitor Based on iso-Combretastatin A-4

  摘要：

  Designing multitarget drugs have raised considerable interest due to their advantages in the treatment of complex diseases such as cancer. Their design constitutes a challenge in antitumor drug discovery. The present study reports a dual inhibition of tubulin polymerization and HDAC activity. On the basis of 1,1-diarylethylenes (isoCA-4) and belinostat, a series of hybrid molecules was successfully designed and synthesized. In particular compounds, 5f and 5h were proven to be potent inhibitors of both tubulin polymerization and HDAC8 leading to excellent antiproliferative activity.

  DOI：

  10.1021/acs.jmedchem.8b00050
• 作为产物：
  描述：

  5-溴吲哚 在 二甲基氯化铝 、 sodium hydride 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 3.5h， 生成 ethyl 5-bromo-1-methyl-1H-indole-3-carboxylate
  参考文献：
  名称：

  Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles

  摘要：

  Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by de-protonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.12.028

文献信息

• AMIDE DERIVATIVE AND USE THEREOF
  申请人：Ushio Hiroyuki

  公开号：US20130211075A1

  公开（公告）日：2013-08-15

  The present invention relates to a novel amide derivative. More specifically, the present invention provides a medicinal agent useful as a prophylactic or therapeutic agent for diseases, which relies on the production of cytokines from T cells, and which comprises an amide derivative or a pharmacologically acceptable salt thereof or a solvate of the derivative or the pharmacologically acceptable salt as an active ingredient. Provided is an amide derivative represented by general formula (I) [wherein each symbol is as defined in the description] or a pharmacologically acceptable salt thereof, or a solvate of the derivative or the pharmacologically acceptable salt.

  本发明涉及一种新型酰胺衍生物。更具体地说，本发明提供了一种药用剂，可用作依赖于T细胞产生细胞因子的疾病的预防或治疗剂，该药用剂包括酰胺衍生物或其药理学上可接受的盐或该衍生物或药理学上可接受的盐的溶剂的溶剂作为活性成分。提供的是由通式(I)所表示的酰胺衍生物[其中每个符号如描述中所定义]或其药理学上可接受的盐，或该衍生物或药理学上可接受的盐的溶剂。
• Amide derivative and use thereof
  申请人：Ushio Hiroyuki

  公开号：US09150555B2

  公开（公告）日：2015-10-06

  The present invention relates to a novel amide derivative. More specifically, the present invention provides a medicinal agent useful as a prophylactic or therapeutic agent for diseases, which relies on the production of cytokines from T cells, and which comprises an amide derivative or a pharmacologically acceptable salt thereof or a solvate of the derivative or the pharmacologically acceptable salt as an active ingredient. Provided is an amide derivative represented by general formula (I) [wherein each symbol is as defined in the description] or a pharmacologically acceptable salt thereof, or a solvate of the derivative or the pharmacologically acceptable salt.

  本发明涉及一种新型酰胺衍生物。更具体地说，本发明提供了一种药物剂，其可作为预防或治疗疾病的药物剂，依赖于T细胞产生细胞因子，并包括酰胺衍生物或其药理学上可接受的盐或衍生物或药理学上可接受的盐的溶剂作为活性成分。提供了一种由通式（I）表示的酰胺衍生物[其中每个符号如定义中所述]或其药理学上可接受的盐，或其衍生物或药理学上可接受的盐的溶剂。
• Electron Donor–Acceptor Complex Induced Fused Indoles with Hypervalent Iodine(III) Reagents
  作者：Li Liu、Yage Zhang、Wenyan Zhao、Jian Li

  DOI：10.1021/acs.orglett.3c02009

  日期：2023.9.1

  An operationally simple and efficient method for the cyclization of tertiary amines and hypervalent iodine reagents enabled by an EDA complex has been developed. A series of [1,2-α]indoles derivatives were obtained in good yields, including some key intermediates for the synthesis of biologically active molecules. In addition, this established strategy features a broad substrate scope and good functional

  已经开发出一种操作简单且有效的通过 EDA 复合物实现叔胺和高价碘试剂环化的方法。以良好的收率获得了一系列[1,2-α]吲哚衍生物，其中包括一些用于合成生物活性分子的关键中间体。此外，该既定策略具有广泛的底物范围和良好的官能团耐受性。
• US9150555B2
  申请人：——

  公开号：US9150555B2

  公开（公告）日：2015-10-06
• Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles
  作者：Koji Nemoto、Shinya Tanaka、Megumi Konno、Satoru Onozawa、Masafumi Chiba、Yuuki Tanaka、Yosuke Sasaki、Ryo Okubo、Tetsutaro Hattori

  DOI：10.1016/j.tet.2015.12.028

  日期：2016.2

  Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by de-protonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively. (C) 2015 Elsevier Ltd. All rights reserved.