(R)-(5-cyano-8-methyl-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid | 463941-20-0

• 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: (R)-(5-cyano-8-methyl-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid
• 英文别名: (R)-5-cyano-8-methyl-1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]-indolyl-1-acetic acid；(R)-5-cyano-8-methyl-1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid；Pyrano(3,4-b)indole-1-acetic acid, 5-cyano-1,3,4,9-tetrahydro-8-methyl-1-propyl-, (1R)-；2-[(1R)-5-cyano-8-methyl-1-propyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl]acetic acid
• CAS: 463941-20-0
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: JXZYSNWHGBGZAI-GOSISDBHSA-N

物化性质

• 沸点：
  575.2±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  86.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(5-cyano-8-methyl-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 以88%的产率得到1-(R)-N-(4-bromobenzyl)-2-(5-cyano-8-fluoro-1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-yl)-acetamide
  参考文献：
  名称：

  [EN] METHOD FOR THE USE OF PYRANOINDOLE DERIVATIVES TO TREAT INFECTION WITH HEPATITIS C VIRUS
  [FR] METHODE D'UTILISATION DE DERIVES DU PYRANOINDOLE POUR TRAITER UNE INFECTION PAR LE VIRUS DE L'HEPATITE C

  摘要：

  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。

  公开号：

  WO2003099275A1
• 作为产物：
  描述：

  5-bromo-8-methyl-1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid ethyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 甲醇 为溶剂， 反应 0.25h， 生成 (R)-(5-cyano-8-methyl-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-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

文献信息

• Process for the scalable synthesis of 1,3,4,9-tetrahydropyrano[3,4-b]-indole derivatives
  申请人：Chew Warren

  公开号：US20060058532A1

  公开（公告）日：2006-03-16

  The invention is directed to a process of synthesizing compounds of formula (VI): wherein R 1- R 9 , R 3′ , R 4′ and Y are as set forth in the specification, and said method is useful for large scale synthesis thereof. The invention is also directed to useful intermediates for synthesizing the compounds of formula (VI) and processes of preparing said intermediates.

  本发明涉及一种合成化合物的方法，其化学式为（VI）：其中R1-R9，R3'，R4'和Y如规范中所述，该方法适用于大规模合成。本发明还涉及用于合成化合物的有用中间体以及制备该中间体的方法。
• [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。
• Process for preparing isatins with control of side-product formation
  申请人：Wilk Kazimierz Bogdan

  公开号：US20060247442A1

  公开（公告）日：2006-11-02

  Methods and kits for preventing or minimizing the formation of isatin oximes during formation of an isatin from an isonitrosoacetanilide are provided. Also provided are methods and kits for preventing or minimizing the formation of isatin oxime impurities after formation of an isatin from an isonitrosoacetanilide by using a decoy agent in the quenching and/or extraction steps. The isatins can be prepared using a decoy agent and desirably a strong acid. Further provided are methods for preparing isatin oximes.

  提供了一种防止或最小化在从异硝基乙酰苯胺制备异吲哚时形成异吲哚肟的方法和试剂盒。还提供了一种使用诱饵剂在淬灭和/或提取步骤中防止或最小化从异硝基乙酰苯胺制备异吲哚后形成异吲哚肟杂质的方法和试剂盒。可以使用诱饵剂和强酸制备异吲哚。还提供了制备异吲哚肟的方法。
• Method for the use of pyranoindole derivatives to treat infection with Hepatitis C virus
  申请人：Wyeth

  公开号：US20040082643A1

  公开（公告）日：2004-04-29

  The invention is directed to methods of treating, preventing, or inhibiting a Hepatitis C viral infection in a mammal comprising contacting the mammal with an effective amount of a compound of the formula: 1 Wherein substitutions at R 1 , R 2 , R 3 -R 12 , and Y are set forth in the specification.

  本发明涉及一种用于治疗、预防或抑制哺乳动物体内丙型肝炎病毒感染的方法，包括将哺乳动物与公式1中的化合物的有效量接触。其中，R1、R2、R3-R12和Y的取代基在规范中说明。
• R-enantiomers of pyranoindole derivatives and the use thereof for the treatment of hepatitis C virus infection or disease
  申请人：Wyeth

  公开号：US20040029947A1

  公开（公告）日：2004-02-12

  The invention is directed to a compound and a pharmaceutical composition of the formula: 1 Wherein substitutions at R 1 , R 2 , R 3 -R 12 , and Y are set forth in the specification.

  该发明涉及一种化合物和药物组合物，其化学式为：1，其中R1、R2、R3-R12和Y的取代基在说明书中给出。