5-phenylindole-2-carboxylicacid | 66616-71-5

• 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: 5-phenylindole-2-carboxylicacid
• 英文别名: 5-Phenyl-2-indolylcarbonsaeure；5-phenyl-1H-indole-2-carboxylic acid
• CAS: 66616-71-5
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: ZFGZSZKIDKLLQE-UHFFFAOYSA-N

物化性质

• 熔点：
  245-246 °C (decomp)
• 沸点：
  521.2±30.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 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：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-phenylindole-2-carboxylicacid 反应 0.08h， 以55%的产率得到5-苯基-1H-吲哚
  参考文献：
  名称：

  5-芳基-、2,5-二芳基-和2-乙氧基羰基-5-芳基-吲哚的一些新衍生物

  摘要：

  合成了 5-芳基-、2.5-二芳基-和 2-乙氧基羰基-5-芳基-吲哚的一些衍生物。描述了 5-苯基吲哚-2-羧酸乙酯的一些反应。表明α-乙氧羰基对吲哚取代反应具有空间位阻和电子受体影响。所有新化合物的结构均通过 IR、UV、1 H NMR、13 C NMR 和元素分析确认。

  DOI：

  10.3998/ark.5550190.0013.613
• 作为产物：
  描述：

  ethyl 5-phenyl-1H-indole-2-carboxylate 在 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 3.0h， 以80%的产率得到5-phenylindole-2-carboxylicacid
  参考文献：
  名称：

  5-芳基-、2,5-二芳基-和2-乙氧基羰基-5-芳基-吲哚的一些新衍生物

  摘要：

  合成了 5-芳基-、2.5-二芳基-和 2-乙氧基羰基-5-芳基-吲哚的一些衍生物。描述了 5-苯基吲哚-2-羧酸乙酯的一些反应。表明α-乙氧羰基对吲哚取代反应具有空间位阻和电子受体影响。所有新化合物的结构均通过 IR、UV、1 H NMR、13 C NMR 和元素分析确认。

  DOI：

  10.3998/ark.5550190.0013.613

文献信息

• [EN] SECO-CYCLOPROPAPYRROLOINDOLE COMPOUNDS, ANTIBODY-DRUG CONJUGATES THEREOF, AND METHODS OF MAKING AND USE<br/>[FR] COMPOSÉS DE SECO-CYCLOPROPAPYRROLOINDOLE, CONJUGUÉS ANTICORPS-MÉDICAMENT DE CEUX-CI, ET PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2018035391A1

  公开（公告）日：2018-02-22

  seco-Cyclopropapyrroloindole compounds of formula (I) where Hal, R1, R2, and R3 are as defined in the application, are potent anti-cancer agents that can be used in antibody-drug conjugates.

  公式（I）中的seco-Cyclopropapyrroloindole化合物，其中Hal、R1、R2和R3如申请中定义，是强效的抗癌药物，可以用于抗体药物偶联物。
• Certain Nitrogen Containing Bicyclic Chemical Entities For Treating Viral Infections
  申请人：Schmitz Franz Ulrich

  公开号：US20120121540A1

  公开（公告）日：2012-05-17

  Provided are certain chemical entities, pharmaceutical compositions, and methods of treatment of a member of the flaviviradae family of viruses such as hepacivirus (Hepatitis C or HCV).

  提供了某些化学实体、制药组合物和治疗方法，用于治疗黄病毒科的成员，例如丙型肝炎病毒（丙肝或HCV）。
• Certain nitrogen containing bicyclic chemical entities for treating viral infections
  申请人：Schmitz Franz Ulrich

  公开号：US20090176778A1

  公开（公告）日：2009-07-09

  Provided are certain chemical entities, pharmaceutical compositions, and methods of treatment of a member of the flaviviradae family of viruses such as hepacivirus (Hepatitis C or HCV).

  提供了某些化学实体、药物组合物和治疗方法，用于治疗黄病毒科家族成员，如丙型肝炎病毒（Hepatitis C或HCV）。
• Discovery of <i>N</i>-Hydroxyindole-Based Inhibitors of Human Lactate Dehydrogenase Isoform A (LDH-A) as Starvation Agents against Cancer Cells
  作者：Carlotta Granchi、Sarabindu Roy、Chiara Giacomelli、Marco Macchia、Tiziano Tuccinardi、Adriano Martinelli、Mario Lanza、Laura Betti、Gino Giannaccini、Antonio Lucacchini、Nicola Funel、Leticia G. León、Elisa Giovannetti、Godefridus J. Peters、Rahul Palchaudhuri、Emilia C. Calvaresi、Paul J. Hergenrother、Filippo Minutolo

  DOI：10.1021/jm101007q

  日期：2011.3.24

  Highly invasive tumor cells are characterized by a metabolic switch, known as the Warburg effect, from "normal" oxidative phosphorylation to increased glycolysis even under. sufficiently oxygenated conditions. This dependence on glycolysis also confers a growth advantage to cells present in hypoxic regions of the tumor. One of the key enzymes involved in glycolysis, the muscle isoform of lactate dehydrogenase (LDH-A), is overexpressed by metastatic cancer cells and is linked to the vitality of tumors in hypoxia. This enzyme may be considered as a potential target for new anticancer agents, since its inhibition cuts cancer energetic and anabolic supply, thus reducing the metastatic and invasive potential of cancer cells. We have discovered new and efficient N-hydroxyindole-based inhibitors of LDH-A, which are isoform-selective (over LDH-B) and competitive with both the substrate (pyruvate) and the cofactor (NADH). The antiproliferative activity of these compounds was confirmed on a series of cancer cell lines, and they proved to be particularly effective under hypoxic conditions. Moreover, NMR experiments showed that these compounds are able to reduce the glucose-to-lactate conversion inside the cell.
• Novel 3,4-Dihydroquinolin-2(1 H )-one inhibitors of human glycogen phosphorylase a
  作者：Keith G. Rosauer、Anthony K. Ogawa、Chris A. Willoughby、Kenneth P. Ellsworth、Wayne M. Geissler、Robert W. Myers、Qiaolin Deng、Kevin T. Chapman、Georgianna Harris、David E. Moller

  DOI：10.1016/j.bmcl.2003.09.022

  日期：2003.12

  The preparation of a series of substituted indoles coupled to six- and seven-membered cyclic lactams is described and their role as human glycogen phosphorylase a inhibitors discussed. The SAR of the indole moiety and lactam ring are presented. (C) 2003 Elsevier Ltd. All rights reserved.