(E)-3-(1H-吲哚-2-基)丙烯酸 | 143618-94-4

• 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
• 中文名称: (E)-3-(1H-吲哚-2-基)丙烯酸
• 英文名称: (E)-3-(1H-indol-2-yl)acrylic acid
• 英文别名: (2E)-3-(1H-indol-2-yl)prop-2-enoic acid；(E)-3-(1H-indol-2-yl)prop-2-enoic acid
• CAS: 143618-94-4
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: SXOUIMVOMIGLHO-AATRIKPKSA-N

物化性质

• 沸点：
  432.8±20.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(1H-吲哚-2-基)丙烯酸 在 sodium hydroxide 、 PPA 、 二苯基膦叠氮化物 、 盐酸羟胺 、 sodium acetate 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 乙醇 、 氯仿 、 水 、 乙腈 、 xylene 为溶剂， 反应 39.67h， 生成 3-氨基-1-甲基-5H-吡啶[4,3-b]吲哚
  参考文献：
  名称：

  Synthesis of genotoxic heterocyclic amines Trp-P-1 and Trp-P-2

  摘要：

  Trp-P-1 (1a) and Trp-P-2 (1b) possessing a pyrido[4,3-b]indole system have been newly synthesized. The key reaction step in the synthetic sequence has been the thermal electrocyclic reaction of the 1-azahexa-1,3,5-triene system 3 involving the indole [b] bond derived from 2-vinylindoles 4. 2-Vinylindole 4a has been derived from N-(benzenesulfonyl)indole (5) in a four-step sequence. 2-Vinylindole 4b has been synthesized by two routes using either ethoxymethylidene Meldrum's acid (6b) or diethyl ethoxymethylidenemalonate (10) as Michael acceptors to the 2-lithio-N-(benzenesulfonyl)indole.

  DOI：

  10.1021/jo00048a026
• 作为产物：
  描述：

  (E)-methyl 3-(1-benzoyl-1H-indol-2-yl)acrylate 在 水 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 0.75h， 以93%的产率得到(E)-3-(1H-吲哚-2-基)丙烯酸
  参考文献：
  名称：

  使用N-苄基直接基团的吲哚的高度区域选择性C 2-烯基化：有效的Ru催化偶联反应

  摘要：

  使用Ru（II）催化剂，通过采用直接基团策略，已实现了吲哚在C2位的高区域选择性烯基化。在存在吲哚的更活泼的C 3和C 7位置以及苯甲酰基保护基的邻位的情况下，该策略为在C-2位置的烯基化N-苯甲酰基吲哚提供了罕见的选择性。还已经举例说明了苯甲酰基的简单脱保护，并且所得产物用作天然产物合成的有用的合成子。

  DOI：

  10.1021/ol4011486

文献信息

• NOVEL LOW-MOLECULAR-COMPOUND FOR IMPROVING PRODUCTION, MAINTENANCE AND PROLIFERATION OF PLURIPOTENT STEM CELLS, COMPOSITION COMPRISING THE SAME, AND CULTURE METHOD
  申请人：KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY

  公开号：US20150159142A1

  公开（公告）日：2015-06-11

  According to the present invention, when the novel low-molecular-weight compound RSC-133 is added in a culture process for producing reprogrammed pluripotent stem cells from human differentiated cells, it can increase the efficiency of reprogramming and can significantly reduce the time required for the induction of reprogramming. Particularly, the novel compound RSC-133 can substitute for c-Myc acting as both a reprogramming factor and an oncogenic factor, and it can effectively increase the efficiency of reprogramming in both normal oxygen culture conditions and hypoxic culture conditions. In addition, RSC-133 can inhibit the induction of aging occurring in the reprogramming process, exhibits the effect of promoting cell proliferation, and induces epigenetic activation to improve culture conditions for induction of reprogramming. The present invention will contribute to optimizing a process of producing induced pluripotent stem cells from a small amount of patient-specific somatic cells obtained from various sources, and thus it will significantly improve a process of developing clinically applicable personalized stem cell therapy agents and new drugs and will facilitate the practical use of these agents and drugs. In addition, the novel low-molecular-weight compound RSC-133 can provide a cell culture medium effective for maintaining the undifferentiated state of human embryonic stem cells that are typical pluripotent stem cells. The medium composition containing RSC-133 can effectively induce the proliferation of human embryonic stem cells in an undifferentiated state and can be effectively used for the development of a system for culturing large amounts of embryonic stem cells.

  根据本发明，当在从人类分化细胞生产重编程的多能干细胞的文化过程中添加新型的低分子量化合物RSC-133时，它可以提高重编程的效率，并且可以显著减少诱导重编程所需的时间。特别是，新型化合物RSC-133可以替代作为重编程因子和致癌因子的c-Myc，并且可以在正常氧文化条件和无氧文化条件下有效地提高重编程的效率。此外，RSC-133可以抑制在重编程过程中发生的衰老诱导，表现出促进细胞增殖的效果，并诱导表观遗传激活以改善重编程诱导的培养条件。本发明将有助于优化从各种来源获得的患者特异性体细胞的小量生产诱导多能干细胞的过程，从而将显著改进开发临床应用的个人化干细胞治疗剂和新药的过程，并将促进这些剂和药物的实用化。另外，新型的低分子量化合物RSC-133可以提供一个有效的细胞培养介质，用于维持典型多能干细胞的人胚胎干细胞的不分化状态。含有RSC-133的培养基质可以有效诱导人胚胎干细胞在不分化状态的增殖，并且可以有效地用于大量胚胎干细胞培养系统的开发。
• Process for producing dipeptides or dipeptide derivatives
  申请人：Hashimoto Shin-ichi

  公开号：US20050287627A1

  公开（公告）日：2005-12-29

  The present invention provides a process for producing a dipeptide or a dipeptide derivative using a phosphate donor, a substance selected from the group consisting of adenosine-5′-monophosphate, adenosine-5′-diphosphate and adenosine-5′-triphosphate, one or more kinds of amino acids or amino acid derivatives, and as enzyme sources, a protein having polyphosphate kinase activity, or a culture of cells having the ability to produce the protein or a treated matter of the culture, and a protein having the activity to ATP-dependently form the dipeptide or dipeptide derivative from one or more kinds of amino acids or amino acid derivatives, or a culture of cells having the ability to produce the protein or a treated matter of the culture.

  本发明提供了一种利用磷酸供体、从腺苷-5′-单磷酸、腺苷-5′-二磷酸和腺苷-5′-三磷酸组成的一组物质中选择的物质、一种或多种氨基酸或氨基酸衍生物，以及作为酶源的具有多磷酸激酶活性的蛋白质，或者具有产生该蛋白质的能力的细胞培养物，以及具有ATP依赖性形成该二肽或二肽衍生物的活性蛋白质，或者具有产生该蛋白质的能力的细胞培养物或经处理的培养物质的生产二肽或二肽衍生物的过程。
• Process For Producing Dipeptides or Dipeptide Derivatives
  申请人：Hashimoto Shin-ichi

  公开号：US20080213827A1

  公开（公告）日：2008-09-04

  The present invention provides a process for producing a dipeptide or a dipeptide derivative by using a protein having the activity to form the dipeptide or dipeptide derivative from one or more kinds of amino acids or amino acid derivatives, or a culture of cells having the ability to produce the protein or a treated matter of the culture as a enzyme source, which comprise; allowing the enzyme source, one or more kinds of amino acids or amino acid derivatives and ATP to be present in an aqueous medium; allowing the dipeptide or dipeptide derivative to form and accumulate in the medium; and recovering the dipeptide or dipeptide derivative from the medium.

  本发明提供了一种通过利用具有形成二肽或二肽衍生物的活性的蛋白质，从一种或多种氨基酸或氨基酸衍生物中形成二肽或二肽衍生物的过程，或者具有产生该蛋白质的能力的细胞培养物或经处理的培养物作为酶源的方法，包括： 使酶源、一种或多种氨基酸或氨基酸衍生物和ATP存在于水性介质中； 使二肽或二肽衍生物形成并在介质中积累；以及 从介质中回收二肽或二肽衍生物。
• Aerobic Ru-catalyzed direct C2-olefination of N-heteroarenes with alkenes directed by a removable N-dimethylcarbamoyl group
  作者：Luo-Qiang Zhang、Shiping Yang、Xiaolei Huang、Jingsong You、Feijie Song

  DOI：10.1039/c3cc44787a

  日期：——

  A highly efficient and selective Ru-catalyzed direct C2-olefination of indoles, pyrroles, and carbazoles assisted by a removable N-dimethylcarbamoyl group has been developed by using O2 as the terminal oxidant. Both electron-deficient and unactivated alkenes are applicable to the protocol.

  一种高效且具有选择性的Ru催化直接C2氧化偶联吲哚、吡咯和咔唑的方法已成功开发，该方法利用O2作为终端氧化剂，并在可移除的N-二甲基氨基甲酰基团辅助下进行。此工艺不仅适用于电子贫乏的烯烃，也适用于未经活化的烯烃。
• Regioselective C2 Oxidative Olefination of Indoles and Pyrroles through Cationic Rhodium(III)-Catalyzed CH Bond Activation
  作者：Bin Li、Jianfeng Ma、Weijia Xie、Haibin Song、Shansheng Xu、Baiquan Wang

  DOI：10.1002/chem.201301987

  日期：2013.9.2

  Be economic with your atoms! An efficient Rh‐catalyzed oxidative olefination of indoles and pyrroles with broad substrate scope and tolerance is reported (see scheme). The catalytic reaction proceeds with excellent regio‐ and stereoselectivity. The directing group N,N‐dimethylcarbamoyl was crucial for the reaction and could be removed easily.

  与您的原子经济！据报道，吲哚和吡咯的高效Rh催化氧化烯化反应具有广泛的底物范围和耐受性（参见方案）。催化反应以优异的区域选择性和立体选择性进行。N，N-二甲基氨基甲酰基导向基团对反应至关重要，可以很容易地除去。