7-chloro-N-(4-chloro-3-((4-ethylpiperazin-1-yl)methyl)phenyl)quinolin-4-amine | 1138471-11-0

• 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
• 英文名称: 7-chloro-N-(4-chloro-3-((4-ethylpiperazin-1-yl)methyl)phenyl)quinolin-4-amine
• 英文别名: 7-chloro-N-[4-chloro-3-[(4-ethylpiperazin-1-yl)methyl]phenyl]quinolin-4-amine
• CAS: 1138471-11-0
• 化学式: C₂₂H₂₄Cl₂N₄
• 分子量: 415.365
• InChiKey: RMYFRGYSVISRAH-UHFFFAOYSA-N

物化性质

• 沸点：
  537.5±50.0 °C(predicted)
• 密度：
  1.291±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  31.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-乙基哌嗪 、 5-(7-chloroquinolin-4-ylamino)-2-chlorobenzaldehyde 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以63%的产率得到7-chloro-N-(4-chloro-3-((4-ethylpiperazin-1-yl)methyl)phenyl)quinolin-4-amine
  参考文献：
  名称：

  Synthesis, Antimalarial Activity, and Preclinical Pharmacology of a Novel Series of 4′-Fluoro and 4′-Chloro Analogues of Amodiaquine. Identification of a Suitable “Back-Up” Compound for N-tert-Butyl Isoquine

  摘要：

  On the basis of a mechanistic understanding of the toxicity of the 4-aminoquinoline arnodiaquine (1b), three series of amodiaquine analogues have been prepared where the 4-aminophenol "metabolic alert" has been modified by replacement of the 4'-hydroxy group with a hydrogen, fluorine, or chlorine atom. Following antimalarial assessment and studies on mechanism of action, two candidates were selected for detailed ADME studies and in vitro and in vivo toxicological assessment. 4'-Fluoro-N-tert-butylamodiaquine (2k) was subsequently identified as a candidate for further development studies based on potent activity versus chloroquine-sensitive and resistant parasites,, moderate to excellent oral bioavailability, low toxicity in in vitro studies, and an acceptable safety profile.

  DOI：

  10.1021/jm8012757