[2-(5-phenylthiazol-2-ylamino)pyridin-4-yl]methanol | 329794-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: [2-(5-phenylthiazol-2-ylamino)pyridin-4-yl]methanol
• 英文别名: [2-(5-Phenyl-thiazol-2-ylamino)-pyridin-4-yl]-methanol；[2-[(5-phenyl-1,3-thiazol-2-yl)amino]pyridin-4-yl]methanol
• CAS: 329794-11-8
• 化学式: C₁₅H₁₃N₃OS
• 分子量: 283.354
• InChiKey: VULQAWNUAOQVTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  86.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2-(5-phenylthiazol-2-ylamino)pyridin-4-yl]methanol 在 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 17.5h， 生成 (5-phenyl-thiazol-2-yl)-(4-pyrrolidin-1-ylmethyl-pyridin-2-yl)-amine
  参考文献：
  名称：

  Potent N-(1,3-Thiazol-2-yl)pyridin-2-amine Vascular Endothelial Growth Factor Receptor Tyrosine Kinase Inhibitors with Excellent Pharmacokinetics and Low Affinity for the hERG Ion Channel

  摘要：

  A series of N-(1,3-thiazol-2-yl)pyridin-2-amine KDR kinase inhibitors have been developed that possess optimal properties. Compounds have been discovered that exhibit excellent in vivo potency. The particular challenges of overcoming hERG binding activity and QTc increases in vivo in addition to achieving good pharmacokinetics have been acomplished by discovering a unique class of amine substituents. These compounds have a favorable kinase selectivity profile that can be accentuated with appropriate substitution.

  DOI：

  10.1021/jm049697f
• 作为产物：
  描述：

  4-(叔丁基二甲基甲硅烷氧基甲基)-吡啶-2-胺 在 sodium hydride 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 [2-(5-phenylthiazol-2-ylamino)pyridin-4-yl]methanol
  参考文献：
  名称：

  Potent N-(1,3-Thiazol-2-yl)pyridin-2-amine Vascular Endothelial Growth Factor Receptor Tyrosine Kinase Inhibitors with Excellent Pharmacokinetics and Low Affinity for the hERG Ion Channel

  摘要：

  A series of N-(1,3-thiazol-2-yl)pyridin-2-amine KDR kinase inhibitors have been developed that possess optimal properties. Compounds have been discovered that exhibit excellent in vivo potency. The particular challenges of overcoming hERG binding activity and QTc increases in vivo in addition to achieving good pharmacokinetics have been acomplished by discovering a unique class of amine substituents. These compounds have a favorable kinase selectivity profile that can be accentuated with appropriate substitution.

  DOI：

  10.1021/jm049697f

文献信息

• Tyrosine kinase inhibitors
  申请人：——

  公开号：US20030064996A1

  公开（公告）日：2003-04-03

  The present invention relates to compounds which inhibit, regulate and/or modulate tyrosine kinase signal transduction, compositions which contain these compounds, and methods of using them to treat tyrosine kinase-dependent diseases and conditions, such as angiogenesis, cancer, tumor growth, atherosclerosis, age related macular degeneration, diabetic retinopathy, inflammatory diseases, and the like in mammals.

  本发明涉及抑制、调节和/或调控酪氨酸激酶信号转导的化合物，包含这些化合物的组合物，以及使用它们治疗哺乳动物中的酪氨酸激酶依赖性疾病和状况的方法，例如血管生成、癌症、肿瘤生长、动脉硬化、老年黄斑变性、糖尿病视网膜病变、炎症性疾病等。
• Potent <i>N</i>-(1,3-Thiazol-2-yl)pyridin-2-amine Vascular Endothelial Growth Factor Receptor Tyrosine Kinase Inhibitors with Excellent Pharmacokinetics and Low Affinity for the hERG Ion Channel
  作者：Mark T. Bilodeau、Adrienne E. Balitza、Timothy J. Koester、Peter J. Manley、Leonard D. Rodman、Carolyn Buser-Doepner、Kathleen E. Coll、Christine Fernandes、Jackson B. Gibbs、David C. Heimbrook、William R. Huckle、Nancy Kohl、Joseph J. Lynch、Xianzhi Mao、Rosemary C. McFall、Debra McLoughlin、Cynthia M. Miller-Stein、Keith W. Rickert、Laura Sepp-Lorenzino、Jennifer M. Shipman、Raju Subramanian、Kenneth A. Thomas、Bradley K. Wong、Sean Yu、George D. Hartman

  DOI：10.1021/jm049697f

  日期：2004.12.1

  A series of N-(1,3-thiazol-2-yl)pyridin-2-amine KDR kinase inhibitors have been developed that possess optimal properties. Compounds have been discovered that exhibit excellent in vivo potency. The particular challenges of overcoming hERG binding activity and QTc increases in vivo in addition to achieving good pharmacokinetics have been acomplished by discovering a unique class of amine substituents. These compounds have a favorable kinase selectivity profile that can be accentuated with appropriate substitution.