5-methyl-3-(quinolinyl-8-sulfonyloxy)phenol | 197959-98-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-methyl-3-(quinolinyl-8-sulfonyloxy)phenol
• 英文别名: (3-hydroxy-5-methylphenyl) quinoline-8-sulfonate
• CAS: 197959-98-1
• 化学式: C₁₆H₁₃NO₄S
• 分子量: 315.35
• InChiKey: IQYRHKOBLDVFCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  76.49
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-methyl-3-(quinolinyl-8-sulfonyloxy)phenol 在 焦磷酸硫胺素 、 caesium carbonate 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 Quinoline-8-sulfonic acid 3-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-propoxy]-5-methyl-phenyl ester
  参考文献：
  名称：

  Oxyguanidines: application to non-peptidic phenyl-based thrombin inhibitors

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(03)00125-2
• 作为产物：
  描述：

  3,5-二羟基甲苯 、 喹啉-8-磺酰氯 在 碳酸氢钠 作用下， 以 乙醚 为溶剂， 生成 5-methyl-3-(quinolinyl-8-sulfonyloxy)phenol
  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

• AMIDINOHYDRAZONES AS PROTEASE INHIBITORS
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP0906091B1

  公开（公告）日：2006-10-04