3-[5-methyl-3-(quinolinyl-8-sulfonyloxy)phenoxy]propanol | 197959-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[5-methyl-3-(quinolinyl-8-sulfonyloxy)phenoxy]propanol
• 英文别名: [3-(3-hydroxypropoxy)-5-methylphenyl] quinoline-8-sulfonate
• CAS: 197959-99-2
• 化学式: C₁₉H₁₉NO₅S
• 分子量: 373.43
• InChiKey: CXCXMSKRJLYSAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  85.72
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-[5-methyl-3-(quinolinyl-8-sulfonyloxy)phenoxy]propanol 在 pyridine-SO3 complex 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 3-[5-methyl-3-(quinolinyl-8-sulfonyloxy)phenoxy]propionaldehyde
  参考文献：
  名称：

  AMIDINOHYDRAZONES AS PROTEASE INHIBITORS

  摘要：

  公开号：

  EP0906091B1
• 作为产物：
  描述：

  喹啉-8-磺酰氯 在 碳酸氢钠 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 为溶剂， 生成 3-[5-methyl-3-(quinolinyl-8-sulfonyloxy)phenoxy]propanol
  参考文献：
  名称：

  Amidinohydrazones as guanidine bioisosteres: application to a new class of potent, selective and orally bioavailable, non-amide-based small-molecule thrombin inhibitors

  摘要：

  We describe a new class of potent, non-amide-based small molecule thrombin inhibitors in which an amidinohydrazone is used as a guanidine bioisostere on a non-peptide scaffold. Compound 4 exhibits nM inhibition of thrombin, is selective for thrombin, and shows 60 and 23% bioavailability in rabbits and dogs, respectively. Crystallographic analysis of 4 bound to thrombin confirmed the amindinohydrazone binding mode. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00632-0

文献信息

• Oxyguanidines: application to non-peptidic phenyl-based thrombin inhibitors
  作者：Bruce Tomczuk、Tianbao Lu、Richard M Soll、Cynthia Fedde、Aihua Wang、Larry Murphy、Carl Crysler、Malini Dasgupta、Stephen Eisennagel、John Spurlino、Roger Bone

  DOI：10.1016/s0960-894x(03)00125-2

  日期：2003.4

  Although thrombin has been extensively researched with many examples of potent and selective inhibitors, the key characteristics of oral bioavailability and long half-life have been elusive. We report here a novel series non-peptidic phenyl-based, highly potent, highly selective and orally bioavailable thrombin inhibitors using oxyguanidines as guanidine-mimetics. (C) 2003 Elsevier Science Ltd. All rights reserved.