1-acetyl-5-chloro-3-hydroxyindole | 344287-26-9

• 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
• 英文名称: 1-acetyl-5-chloro-3-hydroxyindole
• 英文别名: 5-chloro-N-acetylindol-3(2H)-one；1-acetyl-5-chloro-indol-3-ol；1-Acetyl-5-chlor-indol-3-ol；1-(5-chloro-3-hydroxyindol-1-yl)ethanone；1-(5-chloro-3-hydroxy-indol-yl)ethanone
• CAS: 344287-26-9
• 化学式: C₁₀H₈ClNO₂
• 分子量: 209.632
• InChiKey: VDHWOIHLYUKZNZ-UHFFFAOYSA-N

物化性质

• 熔点：
  163 °C
• 沸点：
  366.4±22.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-acetyl-5-chloro-3-hydroxyindole 在 哌啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 Acetic acid 1-acetyl-5-chloro-2-(2,2-dicyano-1-phenyl-ethyl)-1H-indol-3-yl ester
  参考文献：
  名称：

  Daisley, Roy W.; Elagbar, Zaha A.; Walker, John, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1013 - 1016

  摘要：

  DOI：
• 作为产物：
  描述：

  1-乙酰基-5-氯-1H-吲哚-3-基乙酸酯 在 水 、 sodium sulfite 作用下， 反应 3.0h， 以66%的产率得到1-acetyl-5-chloro-3-hydroxyindole
  参考文献：
  名称：

  AZAINDOLE-INDOLE COUPLED DERIVATIVES, PREPARATION METHODS AND USES THEREOF

  摘要：

  一种新型的氮杂吲哚-吲哚偶联衍生物类，其制备方法、含有这些衍生物的药物组合物以及它们的用途。这些衍生物的共同结构特征是它们通过氮杂吲哚和吲哚双分子在不同位置偶联，形成扩展的π共轭系统。这些衍生物通过多种机制抑制细胞生长和增殖。目前的化合物具有改善的溶解性、增加的生物利用度，因此具有增强的药物作用，减少了药物剂量和不良反应。

  公开号：

  US20100137356A1

文献信息

• AZAINDOLE-INDOLE COUPLED DERIVATIVES, PREPARATION METHODS AND USES THEREOF
  申请人：Cheng Jingcai

  公开号：US20100137356A1

  公开（公告）日：2010-06-03

  A novel class of azaindole-indole coupled derivatives, their preparation methods, pharmaceutical compositions containing the same and the uses thereof. The common structural feature of these derivatives is that they are coupled by azaindole and indole bi-molecule at different positions, forming extended pi-conjugated systems. Such derivatives inhibited cell growth and proliferation by various mechanisms. The present compounds have improved solubility, increased bioavailability, and thus have enhanced drug actions, and reduced medical dosages and undesired responses.

  一种新型的氮杂吲哚-吲哚偶联衍生物类，其制备方法、含有这些衍生物的药物组合物以及它们的用途。这些衍生物的共同结构特征是它们通过氮杂吲哚和吲哚双分子在不同位置偶联，形成扩展的π共轭系统。这些衍生物通过多种机制抑制细胞生长和增殖。目前的化合物具有改善的溶解性、增加的生物利用度，因此具有增强的药物作用，减少了药物剂量和不良反应。
• [EN] N-ARYLALKYL-3-AMINOALKOXYINDOLES AND THEIR USE AS 5-HT LIGANDS<br/>[FR] N-ARYLALKYL-3-AMINOALCOXYINDOLES ET LEUR UTILISATION EN TANT QUE LIGANDS DES RECEPTEURS 5-HT
  申请人：SUVEN LIFE SCIENCES LTD

  公开号：WO2004048331A1

  公开（公告）日：2004-06-10

  The present invention describes substituted 3-Aminoalkoxyindoles, as compounds of the general formula (I), its stereoisomers, its radioisotopes, its geometric forms, its N-oxides, its polymorphs, its pharmaceutically acceptable salts, its pharmaceutically acceptable solvates, its useful bioactive metabolites and any suitable combination of the above. The invention also discloses the processes for preparing such compounds of the general formula (I), its stereoisomers, its radioisotopes, its geometric forms, its N-oxides, its polymorphs, its pharmaceutically acceptable salts, its pharmaceutically acceptable solvates, its useful bio-active metabolites and also includes any suitable combination of the above. Further described are various methods of administering these compounds of general formula (I), i.e. pharmaceutically acceptable dosage forms, their composition and their use in either therapy or diagnosis.

  本发明描述了取代的3-氨基烷氧基吲哚，作为一般式(I)化合物，其立体异构体、放射性同位素、几何形式、N-氧化物、多晶形态、药学上可接受的盐、药学上可接受的溶剂化合物、有用的生物活性代谢物及上述任何合适的组合。该发明还揭示了制备该一般式(I)化合物、其立体异构体、放射性同位素、几何形式、N-氧化物、多晶形态、药学上可接受的盐、药学上可接受的溶剂化合物、有用的生物活性代谢物的方法，并包括上述任何合适的组合。进一步描述了各种给药这些一般式(I)化合物的方法，即药学上可接受的剂型、它们的组成以及它们在治疗或诊断中的用途。
• Azaindole-indole coupled derivatives, preparation methods and uses thereof
  申请人：Cheng Jingcai

  公开号：US08642765B2

  公开（公告）日：2014-02-04

  A novel class of azaindole-indole coupled derivatives, their preparation methods, pharmaceutical compositions containing the same and the uses thereof. The common structural feature of these derivatives is that they are coupled by azaindole and indole bi-molecule at different positions, forming extended pi-conjugated systems. Such derivatives inhibited cell growth and proliferation by various mechanisms. The present compounds have improved solubility, increased bioavailability, and thus have enhanced drug actions, and reduced medical dosages and undesired responses.

  一种新型的氮杂吲哌-吲哌偶联衍生物、其制备方法、含有该衍生物的药物组合物及其用途。这些衍生物的共同结构特征是它们由氮杂吲哌和吲哌双分子在不同位置偶联形成扩展的π共轭系统。这些衍生物通过多种机制抑制细胞生长和增殖。这些化合物具有改善的溶解度、增强的生物利用度，因此具有增强的药物作用，减少了药物剂量和不良反应。
• Vibrational spectra, DFT calculations, and conformations of 5′-chloro-1-isopropyl-7-azaindirubin-3′-oxime
  作者：Timothy J. Robbins、Yongmei Wang、Qi-Zheng Yao、Zhao-Hui Wang、Jingcai Cheng、Ying-Sing Li

  DOI：10.1016/j.molstruc.2013.05.012

  日期：2013.9

  For centuries Danggui Longhui Wan has been used to treat chronic ailments, such as myelocytic leukemia. In the 1960s, the active ingredient in Danggui Longhui Wan was isolated and identified as indirubin. Indirubin has shown potent inhibition of cyclin-dependent kinase through binding to the ATP-binding site. However, indirubin shows poor solubility and low absorption, hence many derivatives have been developed to enhance these properties. One such derivative is 5'-chloro-1-isopropyl-7-azaindirubin-3'oxime (CIADO), investigated in the current work. Infrared and Raman spectra were collected and compared with predicted spectra using density functional theory. Based on theoretical calculations, the most stable form of CIADO isomer is found to be cis (Z) and trans (E) with respect to the ring system linkage and the 3'-oxime functional group respectively. Also observed were two distinct internal rotational minima for the 1-isoprooyl group separated by a large energy barrier. The presence of two distinct isopropyl conformations observed in our calculations was confirmed with temperature-dependent IR experiments. Assignment of experimental vibrational modes was carried out based on functional group displacement observed in the calculations. (c) 2013 Elsevier B.V. All rights reserved.
• DAISLEY, R. W.;ELAGBAR, Z. A.;WALKER, J., J. HETEROCYCL. CHEM., 1982, 19, N 5, 1013-1016
  作者：DAISLEY, R. W.、ELAGBAR, Z. A.、WALKER, J.

  DOI：——

  日期：——