7-[(4-氯苯基)[(3-羟基-2-吡啶基)氨基]甲基]-8-喹啉醇 | 385786-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 7-[(4-氯苯基)[(3-羟基-2-吡啶基)氨基]甲基]-8-喹啉醇
• 英文名称: 7-((4-chlorophenyl)((3-hydroxypyridin-2-yl)amino)methyl)quinolin-8-ol
• 英文别名: adaptaquin；7-{(4-chlorophenyl)[(3-hydroxypyridin-2-yl)amino]methyl}quinolin-8-ol；7-[(4-chlorophenyl)-[(3-hydroxypyridin-2-yl)amino]methyl]quinolin-8-ol
• CAS: 385786-48-1
• 化学式: C₂₁H₁₆ClN₃O₂
• 分子量: 377.83
• InChiKey: KKYHNYRUBSYTCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  650.9±55.0 °C(Predicted)
• 密度：
  1.437±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO 中≤30mg/ml；二甲基甲酰胺中≤30mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  78.3
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-[(4-氯苯基)[(3-羟基-2-吡啶基)氨基]甲基]-8-喹啉醇 在 Chiralpak AD column 作用下， 以 乙醇 、 正己烷 为溶剂， 生成 (+)-adaptaquin 、 (-)-adaptaquin
  参考文献：
  名称：

  Adaptaquin 对映体的抗缺氧活性

  摘要：

  Adaptaquin，7-{(4-chlorophenyl)[(3-hydroxypyridin-2-yl)amino]methyl}quinolin-8-ol (1)，在我们早期的研究中被鉴定为一种缺氧诱导因子 (HIF) 脯氨酰羟化酶通过高通量筛选细胞系，该抑制剂稳定表达编码由 HIF 氧可降解结构域和萤火虫荧光素酶 (HIF1 ODD-luc) 组成的融合蛋白的报告基因构建体。Adaptaquin 是这种酶的特异性抑制剂，在氧化应激的细胞模型和出血性中风的体内模型中表现出神经保护特性。研究了手性碳原子在抑制剂分子中的作用，以进一步改善适应症结构。进行分离成两种对映异构体。两种对映异构体都显示同样激活 HIF1 ODD-luc 报告基因。

  DOI：

  10.1007/s11172-018-2376-0
• 作为产物：
  描述：

  2-氨基-3-羟基吡啶 、 8-羟基喹啉 、 4-氯苯甲醛 以 乙醇 为溶剂， 反应 72.0h， 以34%的产率得到7-[(4-氯苯基)[(3-羟基-2-吡啶基)氨基]甲基]-8-喹啉醇
  参考文献：
  名称：

  Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases

  摘要：

  使用Betti反应高效生成2OG氧化酶抑制剂，包括KDM4去甲基酶。

  DOI：

  10.1039/c5cc06095h

文献信息

• Prolylhydroxylase/ATF4 inhibitors and methods of use for treating neural cell injury or death and conditions resulting therefrom
  申请人：CORNELL UNIVERSITY

  公开号：US10716783B2

  公开（公告）日：2020-07-21

  Methods for treating a patient suffering from neural cell injury, the method comprising administering to the patient an effective amount of a HIF prolyl-4-hydroxylase inhibiting compound having the following general formula (1) wherein R1 is a cyclic group containing at least three and up to seven carbon atoms and optionally containing one or more heteroatoms selected from O, N, and S, and optionally attached to the shown carbon atom by a linking group; R2 is independently selected from said cyclic groups of R1 and acyclic hydrocarbon groups R5 containing up to twenty carbon atoms; R3 is selected from hydrogen atom and hydrocarbon groups containing up to six carbon atoms; R6 and R7 are independently selected from hydrogen atom, hydrocarbon groups containing up to three carbon atoms, halogen atom, and polar groups, as well as methylene-linked versions thereof; and t is 0 or 1.

  治疗神经细胞损伤患者的方法，该方法包括向患者施用有效量的具有下通式(1)的HIF脯氨酰-4-羟化酶抑制化合物 其中R1是含有至少三个至多七个碳原子的环状基团，任选含有一个或多个选自O、N和S的杂原子，并任选通过连接基团连接到所示碳原子；R2 独立地选自 R1 的环状基团和含有多达 20 个碳原子的无环烃基团 R5；R3 选自氢原子和含有多达 6 个碳原子的烃基团；R6 和 R7 独立地选自氢原子、含有多达 3 个碳原子的烃基团、卤素原子和极性基团及其亚甲基连接型；以及 t 为 0 或 1。
• PROLYLHYDROXYLASE/ATF4 INHIBITORS FOR TREATING NEURAL CELL INJURY
  申请人：Cornell University

  公开号：EP3079697B1

  公开（公告）日：2021-02-03
• PROLYLHYDROXYLASE INHIBITORS AND METHODS OF USE
  申请人：Ratan Rajiv R.

  公开号：US20130023528A1

  公开（公告）日：2013-01-24

  Compounds for inhibiting hypoxia inducible factor (HIF) prolyl-4-hydroxylases (PHDs) having the general formula (1). Methods of using these and related compounds for treating a patient having a condition that would benefit from inhibiting HIF PHD are also described herein.
• PROLYLHYDROXYLASE/ATF4 INHIBITORS AND METHODS OF USE FOR TREATING NEURAL CELL INJURY OR DEATH AND CONDITIONS RESULTING THEREFROM
  申请人：CORNELL UNIVERSITY

  公开号：US20160317526A1

  公开（公告）日：2016-11-03

  Methods for treating a patient suffering from neural cell injury, the method comprising administering to the patient an effective amount of a HIF prolyl-4-hydroxylase inhibiting compound having the following general formula (1) wherein R 1 is a cyclic group containing at least three and up to seven carbon atoms and optionally containing one or more heteroatoms selected from O, N, and S, and optionally attached to the shown carbon atom by a linking group; R 2 is independently selected from said cyclic groups of R 1 and acyclic hydrocarbon groups R 5 containing up to twenty carbon atoms; R 3 is selected from hydrogen atom and hydrocarbon groups containing up to six carbon atoms; R 6 and R 7 are independently selected from hydrogen atom, hydrocarbon groups containing up to three carbon atoms, halogen atom, and polar groups, as well as methylene-linked versions thereof; and t is 0 or 1.
• US9505741B2
  申请人：——

  公开号：US9505741B2

  公开（公告）日：2016-11-29