4-fluoro-3-imidazol-1-ylmethyl-phenylamine | 1138471-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-fluoro-3-imidazol-1-ylmethyl-phenylamine
• 英文别名: 4-Fluoro-3-(imidazol-1-ylmethyl)aniline；4-fluoro-3-(imidazol-1-ylmethyl)aniline
• CAS: 1138471-28-9
• 化学式: C₁₀H₁₀FN₃
• 分子量: 191.208
• InChiKey: ICBKAQNNDPGVSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,7-二氯喹啉 、 4-fluoro-3-imidazol-1-ylmethyl-phenylamine 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以46%的产率得到(7-chloroquinolin-4-yl)(4-fluoro-3-imidazol-1-ylmethylphenyl)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
• 作为产物：
  描述：

  1-(2-fluoro-5-nitro-benzyl)-1H-imidazole 在 盐酸 、 tin 、 水 作用下， 反应 1.5h， 以91%的产率得到4-fluoro-3-imidazol-1-ylmethyl-phenylamine
  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