2-(2-Fluoro-4-(2-nitrovinyl)phenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine | 1202077-96-0

• 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: 2-(2-Fluoro-4-(2-nitrovinyl)phenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine
• 英文别名: 2-[2-fluoro-4-(2-nitroethenyl)phenyl]-5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridine
• CAS: 1202077-96-0
• 化学式: C₂₃H₁₆FN₃O₂S
• 分子量: 417.463
• InChiKey: RNTIFFJYOCPHRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-Fluoro-4-(2-nitrovinyl)phenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine 在 水 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 为溶剂， 反应 8.0h， 以27%的产率得到2-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)ethanamine
  参考文献：
  名称：

  Isoform-selective thiazolo[5,4-b]pyridine S1P1 agonists possessing acyclic amino carboxylate head-groups

  摘要：

  Replacement of the azetidine carboxylate of an S1P(1) agonist development candidate, AMG 369, with a range of acyclic head-groups led to the identification of a novel, S1P(3)-sparing S1P(1) agonist, ( )-2-amino -4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)-2-methylbutanoic acid (8c), which possessed good in vivo efficacy and pharmacokinetic properties. A 0.3 mg/kg oral dose of 8c produced a statistically significant reduction in blood lymphocyte counts 24 h post-dosing in female Lewis rats. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.073
• 作为产物：
  描述：

  硝基甲烷 、 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde 在 ammonium acetate 、 溶剂黄146 作用下， 反应 4.0h， 以92%的产率得到2-(2-Fluoro-4-(2-nitrovinyl)phenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine
  参考文献：
  名称：

  Isoform-selective thiazolo[5,4-b]pyridine S1P1 agonists possessing acyclic amino carboxylate head-groups

  摘要：

  Replacement of the azetidine carboxylate of an S1P(1) agonist development candidate, AMG 369, with a range of acyclic head-groups led to the identification of a novel, S1P(3)-sparing S1P(1) agonist, ( )-2-amino -4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)-2-methylbutanoic acid (8c), which possessed good in vivo efficacy and pharmacokinetic properties. A 0.3 mg/kg oral dose of 8c produced a statistically significant reduction in blood lymphocyte counts 24 h post-dosing in female Lewis rats. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.073

文献信息

• S1P1 receptor agonists and use thereof
  申请人：Cee Victor J.

  公开号：US20100029611A1

  公开（公告）日：2010-02-04

  The present invention relates to compounds of Formula (I): that are have activity as S1P receptor modulating agents, more specifically to specifically compounds that are S1P1 receptor agonists. The invention also related to the use of such compounds to treat diseases associated with inappropriate S1P1 receptor activity such as autoimmune diseases.

  本发明涉及式（I）的化合物：具有S1P受体调节剂活性，更具体地说是具有S1P1受体激动剂活性的化合物。本发明还涉及使用这些化合物治疗与不适当的S1P1受体活性相关的疾病，如自身免疫性疾病。