3-[3-(5-chlorothiophenyl-2-sulfonyloxy)-5-methylphenoxy]propanol | 197960-10-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 3-[3-(5-chlorothiophenyl-2-sulfonyloxy)-5-methylphenoxy]propanol
• 英文别名: [3-(3-Hydroxypropoxy)-5-methylphenyl] 5-chlorothiophene-2-sulfonate
• CAS: 197960-10-4
• 化学式: C₁₄H₁₅ClO₅S₂
• 分子量: 362.855
• InChiKey: MRCZEOLKTATJBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[3-(5-chlorothiophenyl-2-sulfonyloxy)-5-methylphenoxy]propanol 在 pyridine-SO3 complex 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 3-[((3E)-3-{[(E)-amino(imino)methyl]hydrazono}propyl)oxy]-5-methylphenyl 5-chlorothiophene-2-sulfonate
  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：

  3-(5-chlorothiophenyl-2-sulfonyloxy)-5-methylphenol 、 1,3-丙二醇 在 三丁基膦 、 1,1'-azodicarbonyl-dipiperidine 作用下， 生成 3-[3-(5-chlorothiophenyl-2-sulfonyloxy)-5-methylphenoxy]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

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

  公开号：EP0906091B1

  公开（公告）日：2006-10-04