2-(4,7-dichloro-indol-3-yl)-ethanol | 57817-20-6

• 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: 2-(4,7-dichloro-indol-3-yl)-ethanol
• 英文别名: 4,7-dichloro tryptophol；4,7-dichlorotryptophol；4,7-Dichlortryptophol；2-(4,7-dichloro-1H-indol-3-yl)ethanol
• CAS: 57817-20-6
• 化学式: C₁₀H₉Cl₂NO
• 分子量: 230.094
• InChiKey: PZYSWOWQOFESBE-UHFFFAOYSA-N

物化性质

• 熔点：
  65-67 °C
• 沸点：
  418.0±40.0 °C(Predicted)
• 密度：
  1.474±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4,7-dichloro-indol-3-yl)-ethanol 在 sodium hydroxide 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (S)-[5,8-dichloro-1-propyl-1,3,4,9-tetrahydropyranoindol-1-yl]acetic acid
  参考文献：
  名称：

  Discovery of Pyrano[3,4-b]indoles as Potent and Selective HCV NS5B Polymerase Inhibitors

  摘要：

  A novel series of HCV NS5B RNA-dependent RNA polymerase inhibitors containing a pyrano-[3,4-b]indole scaffold is described leading to the discovery of compound 16, a highly potent and selective inhibitor that is active in the replicon system.

  DOI：

  10.1021/jm0401255
• 作为产物：
  描述：

  4-[(2,5-dichlorophenyl)hydrazinylidene]butan-1-ol 在 zinc(II) chloride 作用下， 以 乙二醇 为溶剂， 反应 4.0h， 生成 2-(4,7-dichloro-indol-3-yl)-ethanol
  参考文献：
  名称：

  Discovery of Pyrano[3,4-b]indoles as Potent and Selective HCV NS5B Polymerase Inhibitors

  摘要：

  A novel series of HCV NS5B RNA-dependent RNA polymerase inhibitors containing a pyrano-[3,4-b]indole scaffold is described leading to the discovery of compound 16, a highly potent and selective inhibitor that is active in the replicon system.

  DOI：

  10.1021/jm0401255

文献信息

• Etodolic acid and related compounds. Chemistry and antiinflammatory actions of some potent di- and trisubstituted 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acids
  作者：Christopher A. Demerson、Leslie G. Humber、Adolph H. Philipp、Rene R. Martel

  DOI：10.1021/jm00225a010

  日期：1976.3

  4-b]indole-1-acetic acids bearing one, or two, substituents on the benzene ring has been synthesized via the acid-catalyzed condensation of a substituted tryptophol with ethyl propionylacetate or ethyl butyrylacetate. Antiinflammatory and ulcerogenic effects were examined and the results show that 1, 8-diethyl-1, 3, 4, 9-tetrahydropyrano[3, 4-b]indole-1-acetic acid (etodolic acid, USAN) is a potent agent, particularly

  一系列在苯环上带有一个或两个取代基的37种1-乙基和1-n-丙基-1,3,4,9-四氢吡喃[3,4-b]吲哚-1-乙酸通过取代的色酚与丙酸乙酯或丁酸乙酯的酸催化缩合反应合成。检查了抗炎和促溃疡作用，结果表明1、8-二乙基-1、3、4、9-四氢吡喃并[3,4-b]吲哚-1-乙酸（依托度酸，USAN）是有效的药物，在慢性大鼠炎症模型（佐剂性关节炎模型中，ED50 0.7 + 1-0.1 mg / kg po）特别有效，并且在同一物种中具有相对较低的急性致溃疡性。
• [EN] METHOD FOR THE USE OF PYRANOINDOLE DERIVATIVES TO TREAT INFECTION WITH HEPATITIS C VIRUS<br/>[FR] METHODE D'UTILISATION DE DERIVES DU PYRANOINDOLE POUR TRAITER UNE INFECTION PAR LE VIRUS DE L'HEPATITE C
  申请人：WYETH CORP

  公开号：WO2003099275A1

  公开（公告）日：2003-12-04

  The invention is directed to methods of treating, preventing, or inhibiting a Hepatitis C viral infection in a mammal comprising containing the mammal with an effective amount of a compound of the formula: Wherein substitutions at R1, R2, R3-R12, and Y are set forth in the specification.

  这项发明涉及治疗、预防或抑制哺乳动物体内丙型肝炎病毒感染的方法，包括使用有效量的符合以下结构式的化合物来处理哺乳动物：其中R1、R2、R3-R12和Y的取代基在说明书中列出。
• [EN] R-ENANTIOMERS OF PYRANOINDOLE DERIVATIVES AGAINST HEPATITIS C<br/>[FR] ENANTIOMERES R DE DERIVES DE PYRANO-INDOLE DIRIGES CONTRE L'HEPATITE C
  申请人：WYETH CORP

  公开号：WO2003099824A1

  公开（公告）日：2003-12-04

  The invention is directed to a compound and a pharmaceutical composition of the formula: Wherein substitutions at R1, R2, R3 - R12, and Y are set forth in the specification.

  该发明涉及一种化合物和一种药物组合物，其化学式为：其中R1、R2、R3 - R12和Y的取代基在说明书中给出。
• The discovery and structure–activity relationships of pyrano[3,4-b]indole based inhibitors of hepatitis C virus NS5B polymerase
  作者：Matthew G. LaPorte、Tandy L. Draper、Lori E. Miller、Charles W. Blackledge、Lara K. Leister、Eugene Amparo、Alison R. Hussey、Dorothy C. Young、Srinivas K. Chunduru、Christopher A. Benetatos、Gerry Rhodes、Ariamala Gopalsamy、Torsten Herbertz、Christopher J. Burns、Stephen M. Condon

  DOI：10.1016/j.bmcl.2010.03.002

  日期：2010.5

  We describe the structure-activity relationship of the C1-group of pyrano[3,4-b]indole based inhibitors of HCV NS5B polymerase. Further exploration of the allosteric binding site led to the discovery of the significantly more potent compound 12. (C) 2010 Elsevier Ltd. All rights reserved.
• Discovery of Pyrano[3,4-<i>b</i>]indoles as Potent and Selective HCV NS5B Polymerase Inhibitors
  作者：Ariamala Gopalsamy、Kitae Lim、Gregory Ciszewski、Kaapjoo Park、John W. Ellingboe、Jonathan Bloom、Shabana Insaf、Janis Upeslacis、Tarek S. Mansour、Girija Krishnamurthy、Murthy Damarla、Yelena Pyatski、Douglas Ho、Anita Y. M. Howe、Mark Orlowski、Boris Feld、John O'Connell

  DOI：10.1021/jm0401255

  日期：2004.12.1

  A novel series of HCV NS5B RNA-dependent RNA polymerase inhibitors containing a pyrano-[3,4-b]indole scaffold is described leading to the discovery of compound 16, a highly potent and selective inhibitor that is active in the replicon system.