3-[5-methyl-3-(quinolinyl-8-sulfonyloxy)phenoxy]propionaldehyde | 197960-00-2

• 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]propionaldehyde
• 英文别名: [3-methyl-5-(3-oxopropoxy)phenyl] quinoline-8-sulfonate
• CAS: 197960-00-2
• 化学式: C₁₉H₁₇NO₅S
• 分子量: 371.414
• InChiKey: ONYPJGCVSYUWNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 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：
  0.16
• 拓扑面积：
  82.56
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  氨基胍硝酸盐 、 3-[5-methyl-3-(quinolinyl-8-sulfonyloxy)phenoxy]propionaldehyde 生成 3-[((3E)-3-{[(E)-amino(imino)methyl]hydrazono}propyl)oxy]-5-methylphenyl quinolin-8-ylsulfonate
  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
• 作为产物：
  描述：

  喹啉-8-磺酰氯 在 pyridine-SO3 complex 、 碳酸氢钠 、 二甲基亚砜 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 3-[5-methyl-3-(quinolinyl-8-sulfonyloxy)phenoxy]propionaldehyde
  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