5-[3-Fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]pentanoic acid | 1360817-11-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-[3-Fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]pentanoic acid
• CAS: 1360817-11-3
• 化学式: C₂₆H₂₃FN₂O₂S
• 分子量: 446.545
• InChiKey: OPBQWGCTUZRNEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde 在 palladium 10% on activated carbon 、 potassium tert-butylate 、 水 、 氢气 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 生成 5-[3-Fluoro-4-[5-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]phenyl]pentanoic acid
  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

• Isoform-selective thiazolo[5,4-b]pyridine S1P1 agonists possessing acyclic amino carboxylate head-groups
  作者：Anthony B. Reed、Brian A. Lanman、Susana Neira、Paul E. Harrington、Kelvin K.C. Sham、Mike Frohn、Alexander J. Pickrell、Andrew S. Tasker、Anu Gore、Mike Fiorino、Andrea Itano、Michele McElvain、Scot Middleton、Henry Morrison、Han Xu、Yang Xu、Min Wong、Victor J. Cee

  DOI：10.1016/j.bmcl.2011.12.073

  日期：2012.2

  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.