3-[((3E)-3-{[(E)-amino(imino)methyl]hydrazono}propyl)oxy]-5-methylphenyl 2-chlorobenzenesulfonate

• 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-[((3E)-3-{[(E)-amino(imino)methyl]hydrazono}propyl)oxy]-5-methylphenyl 2-chlorobenzenesulfonate
• 英文别名: [3-[(3E)-3-(diaminomethylidenehydrazinylidene)propoxy]-5-methylphenyl] 2-chlorobenzenesulfonate
• 化学式: C₁₇H₁₉ClN₄O₄S
• 分子量: 410.881
• InChiKey: XFNCYOGGBYFMJD-QPSGOUHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氯苯磺酰氯 在 palladium on activated charcoal pyridine-SO3 complex 、 氢气 、 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 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 3-[((3E)-3-{[(E)-amino(imino)methyl]hydrazono}propyl)oxy]-5-methylphenyl 2-chlorobenzenesulfonate
  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 guanidine bioisosteres: application to a new class of potent, selective and orally bioavailable, non-amide-based small-molecule thrombin inhibitors
  作者：Richard M. Soll、Tianobao Lu、Bruce Tomczuk、Carl R. Illig、Cynthia Fedde、Stephen Eisennagel、Roger Bone、Larry Murphy、John Spurlino、F.Raymond Salemme

  DOI：10.1016/s0960-894x(99)00632-0

  日期：2000.1

  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.