(E)-3-(2-(pyridin-3-yl)vinyl)-1H-indole | 53645-37-7

• 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: (E)-3-(2-(pyridin-3-yl)vinyl)-1H-indole
• 英文别名: 3-((E)-2-Pyridin-3-yl-vinyl)-1H-indole；3-[(E)-2-pyridin-3-ylethenyl]-1H-indole
• CAS: 53645-37-7
• 化学式: C₁₅H₁₂N₂
• 分子量: 220.274
• InChiKey: XEGNKAULPJNZHP-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-(pyridin-3-yl)vinyl)-1H-indole 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-methoxy-5-((Z)-3,4,5-trimethoxystyryl)phenyl4-oxo-4-(3-((E)-2-(pyridin-3-yl)vinyl)-1H-indol-1-yl)butanoate
  参考文献：
  名称：

  Microtubule inhibitors containing immunostimulatory agents promote cancer immunochemotherapy by inhibiting tubulin polymerization and tryptophan-2,3-dioxygenase

  摘要：

  A combination therapeutic regimen via introducing tryptophan 2,3-dioxygenase inhibitors into microtubule inhibitors was performed and evaluated for their antitumor activity. Thereinto, HT2, composed of combretastatin A-4 (CA-4) and tryptophan-2,3-dioxygenase (TDO) inhibitor by a linker, displayed the most potent activity with 10-fold higher than its parent CA-4 against HepG2, A549 and HCT-116 cancer cell lines. Mechanism studies suggested that HT2 inhibited tubulin polymerization and cell migration, caused G2 phase arrest, induced apoptosis by mitochondrial mediated apoptotic pathway, concurrent depolarized the mitochondria membrane potentials and caused reactive oxygen species (ROS) production in HepG2 cells. Moreover, HT2 could enhance T-cell immune responses in vitro by releasing a TDO inhibitor to suppress TDO expression and blockade kynurenine production. As expected, HT2 could remarkably promote the antitumor activity of CA-4 in either immunocompetent H22 or immunodeficient A549 tumor xenograft models without observable toxic effects. More importantly, HT2 increased the level of splenic and tumor-infiltrated T cells and in turn effectively boosted the inhibition effect in H22 xenografted tumor growth. Collectively, this immunochemotherapeutic strategy can be applied to promote chemotherapeutic effect. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111949
• 作为产物：
  描述：

  3-吡啶甲醛 、 芦竹碱 在 三丁基膦 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以69%的产率得到(E)-3-(2-(pyridin-3-yl)vinyl)-1H-indole
  参考文献：
  名称：

  膦介导的禾本科植物与醛的偶联：3-乙烯基吲哚的非常简单的合成。

  摘要：

  描述了一种新的和实用的末端取代的3-乙烯基吲哚的合成方法，该方法涉及三丁基膦介导的禾胺与醛的偶联。

  DOI：

  10.1021/ol050484+

文献信息

• Use of derivatives of indoles for the treatment of cancer
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US09212138B2

  公开（公告）日：2015-12-15

  The present invention relates to the use of derivatives of indoles having a general formula (I) as follow: for the manufacture of a pharmaceutical composition intended for the treatment of cancer.

  本发明涉及使用具有以下一般式(I)的吲哚衍生物制备用于治疗癌症的药物组合物。
• USE OF DERIVATIVES OF INDOLES FOR THE TREATMENT OF CANCER
  申请人：GUILLOU Catherine

  公开号：US20130131084A1

  公开（公告）日：2013-05-23

  The present invention relates to the use of derivatives of indoles having a general formula (I) as follow: for the manufacture of a pharmaceutical composition intended for the treatment of cancer.

  本发明涉及使用具有下列通式（I）的吲哚衍生物制造用于治疗癌症的药物组合物。
• Efficient Synthesis of C3‐Alkylated and Alkenylated Indoles via Manganese‐Catalyzed Dehydrogenation
  作者：Mingqin Zhao、Xinyan Li、Xiaoyu Zhang、Zhihui Shao

  DOI：10.1002/asia.202200483

  日期：2022.9

  Indoles are a popular heterocycle scaffold that can be found in various natural products and advanced materials, which are related to our daily life commodities. In this work, we developed an efficient method to synthesize C3-alkylated and alkenylated indoles via manganese-catalyzed dehydrogenative transformation of benzyl alcohols and 2-arylethanols with indoles under mild conditions with high yield

  吲哚是一种流行的杂环支架，可以在与我们日常生活用品有关的各种天然产物和先进材料中找到。在这项工作中，我们开发了一种有效的方法，通过锰催化的苯甲醇和 2-芳基乙醇与吲哚的脱氢转化，在温和的条件下以高产率和选择性合成 C3-烷基化和烯基化吲哚。
• F16 Hybrids Derived from Steviol or Isosteviol Are Accumulated in the Mitochondria of Tumor Cells and Overcome Drug Resistance
  作者：Niels V. Heise、Julia Heisig、Kristof Meier、René Csuk、Thomas Mueller

  DOI：10.3390/molecules29020381

  日期：——

  Steviol and isosteviol were prepared from the commercially available sweetener stevioside and converted into lipophilic F16 hybrids. Their cytotoxicity was determined in SRB assays and showed to depend on both the substitution pattern of the aromatic substituent as well as on the spacer length. Therefore, compound 25 held an IC50 (A2780) of 180 nM, thus surpassing the activity of comparable rhodamine

  甜菊醇和异甜菊醇由市售甜味剂甜菊糖苷制备，并转化为亲脂性 F16 杂交体。它们的细胞毒性在 SRB 测定中测定，并显示取决于芳香族取代基的取代模式以及间隔区长度。因此，化合物 25 的 IC50 （A2780） 为 180 nM，从而超过了同类罗丹明杂交体的活性。几种化合物也能够克服 A2780/A2780cis 模型中的耐药性。额外的染色实验显示，F16 杂交体与成熟的有丝分裂聚糖具有相似的亚细胞积累模式，因此证明了优先的线粒体积累，但也证明了其他细胞区域的一些其他积累。
• [EN] TDO SMALL MOLECULE INHIBITOR DERIVATIVE AND ANTITUMOR CONJUGATE THEREOF, AND PREPARATION METHOD<br/>[FR] DÉRIVÉ INHIBITEUR À PETITES MOLÉCULES TDO, CONJUGUÉ ANTITUMORAL DE CELUI-CI, ET PROCÉDÉ DE PRÉPARATION<br/>[ZH] 一种TDO小分子抑制剂衍生物及其抗肿瘤偶联物和制备方法
  申请人：UNIV SOUTHEAST

  公开号：WO2020019376A1

  公开（公告）日：2020-01-30

  一种TDO小分子抑制剂及其抗肿瘤偶联物和制备方法，该抑制剂为3-(2-吡啶-3-基-乙烯基)-1H-吲哚及其衍生物，其与化疗药物顺铂或伊立替康偶联形成抗肿瘤偶联物，结合化学疗法和免疫疗法的优势，获得了高效低毒、同时具有提高免疫力治疗作用的药物。