8-氯-4-羟基-7-甲氧基-2-(3-三氟甲基-1H-吡唑-1-基)-喹啉 | 1108660-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 8-氯-4-羟基-7-甲氧基-2-(3-三氟甲基-1H-吡唑-1-基)-喹啉
• 英文名称: 8-chloro-7-methoxy-4-hydroxy-2-(3-trifluoromethyl-pyrazol-1-yl)-quinoline
• 英文别名: 8-chloro-4-hydroxy-7-methoxy-2-(3-trifluoromethyl-1H-pyrazol-1-yl)-quinoline；8-chloro-7-methoxy-2-[3-(trifluoromethyl)pyrazol-1-yl]-1H-quinolin-4-one
• CAS: 1108660-13-4
• 化学式: C₁₄H₉ClF₃N₃O₂
• 分子量: 343.693
• InChiKey: VXAFYIBGDVONBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-氯-4-羟基-7-甲氧基-2-(3-三氟甲基-1H-吡唑-1-基)-喹啉 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 34.33h， 生成
  参考文献：
  名称：

  Discovery and structural diversity of the hepatitis C virus NS3/4A serine protease inhibitor series leading to clinical candidate IDX320

  摘要：

  Exploration of the P2 region by mimicking the proline motif found in BILN2061 resulted in the discovery of two series of potent HCV NS3/4A protease inhibitors. X-ray crystal structure of the ligand in contact with the NS3/4A protein and modulation of the quinoline heterocyclic region by structure based design and modeling allowed for the optimization of enzyme potency and cellular activity. This research led to the selection of clinical candidate IDX320 having good genotype coverage and pharmacokinetic properties in various species. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.009
• 作为产物：
  描述：

  2-氯-8-甲基-7-甲氧基-4-(4-甲氧基-苄氧基)-喹啉 在 cerium(III) chloride heptahydrate 、 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.0h， 生成 8-氯-4-羟基-7-甲氧基-2-(3-三氟甲基-1H-吡唑-1-基)-喹啉
  参考文献：
  名称：

  Discovery and structural diversity of the hepatitis C virus NS3/4A serine protease inhibitor series leading to clinical candidate IDX320

  摘要：

  Exploration of the P2 region by mimicking the proline motif found in BILN2061 resulted in the discovery of two series of potent HCV NS3/4A protease inhibitors. X-ray crystal structure of the ligand in contact with the NS3/4A protein and modulation of the quinoline heterocyclic region by structure based design and modeling allowed for the optimization of enzyme potency and cellular activity. This research led to the selection of clinical candidate IDX320 having good genotype coverage and pharmacokinetic properties in various species. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.009

文献信息

• [EN] MACROCYCLIC SERINE PROTEASE INHIBITORS USEFUL AGAINST VIRAL INFECTIONS, PARTICULARLY HCV<br/>[FR] INHIBITEURS MACROCYCLIQUES DE LA SÉRINE PROTÉASE MACROCYCLIQUE UTILES CONTRE LES INFECTIONS VIRALES, EN PARTICULIER LE VIRUS DE L’HÉPATITE C
  申请人：IDENIX PHARMACEUTICALS INC

  公开号：WO2011017389A1

  公开（公告）日：2011-02-10

  Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula (Ia) or (Ib), pharmaceutical compositions comprising the compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.

  本文提供了大环丝氨酸蛋白酶抑制剂化合物，例如，化学式（Ia）或（Ib）所示的化合物，包括这些化合物的药物组合物，以及其制备方法。还提供了它们用于治疗宿主中HCV感染的方法。
• MACROCYCLIC SERINE PROTEASE INHIBITORS
  申请人：Parsy Christophe Claude

  公开号：US20100260710A1

  公开（公告）日：2010-10-14

  Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula Ia or Ib, pharmaceutical compositions comprising the compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.

  本文提供了大环丝氨酸蛋白酶抑制剂化合物，例如，Ia或Ib式的化合物，包括这些化合物的药物组合物，以及其制备方法。还提供了它们用于治疗宿主HCV感染的方法。
• [EN] MACROCYCLIC SERINE PROTEASE INHIBITORS<br/>[FR] INHIBITEURS MACROCYCLIQUES DE LA SÉRINE PROTÉASE
  申请人：IDENIX PHARMACEUTICALS INC

  公开号：WO2009014730A1

  公开（公告）日：2009-01-29

  Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula I, pharmaceutical compositions comprising such compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.

  本文提供了大环丝氨酸蛋白酶抑制剂化合物，例如，Formula I的药物组合物，以及其制备方法。还提供了它们用于治疗宿主HCV感染的方法。
• MACROCYCLIC SERINE PROTEASE INHIBITORS I
  申请人：Parsy Christophe Claude

  公开号：US20090047244A1

  公开（公告）日：2009-02-19

  Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula I, pharmaceutical compositions comprising such compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.

  本文提供了大环丝氨酸蛋白酶抑制剂化合物，例如，公式I所示的化合物，包含这种化合物的制药组合物以及其制备过程。同时，还提供了它们用于治疗宿主中HCV感染的方法。
• Macrocyclic serine protease inhibitors
  申请人：Idenix Pharmaceuticals, Inc.

  公开号：US08093379B2

  公开（公告）日：2012-01-10

  Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula I, pharmaceutical compositions comprising the compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.

  本文提供了宏环丝氨酸蛋白酶抑制剂化合物，例如公式I的化合物，包括该化合物的制药组合物和制备方法。还提供了使用该化合物治疗宿主HCV感染的方法。