[3-(tert-butylaminomethyl)-4-chlorophenyl](7-chloroquinolin-4-yl)amine | 1138471-15-4

• 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: [3-(tert-butylaminomethyl)-4-chlorophenyl](7-chloroquinolin-4-yl)amine
• 英文别名: N-[3-[(tert-butylamino)methyl]-4-chlorophenyl]-7-chloroquinolin-4-amine
• CAS: 1138471-15-4
• 化学式: C₂₀H₂₁Cl₂N₃
• 分子量: 374.313
• InChiKey: XOZXBUKMDWEZOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(7-chloroquinolin-4-ylamino)-2-chlorobenzaldehyde 、 叔丁胺 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59%的产率得到[3-(tert-butylaminomethyl)-4-chlorophenyl](7-chloroquinolin-4-yl)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