1-(2-chloro-5-nitro-benzyl)-4-isopropyl piperazine | 1138471-32-5

• 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: 1-(2-chloro-5-nitro-benzyl)-4-isopropyl piperazine
• 英文别名: 1-(2-chloro-5-nitrobenzyl)-4-isopropyl-piperazine；1-[(2-Chloro-5-nitrophenyl)methyl]-4-propan-2-ylpiperazine
• CAS: 1138471-32-5
• 化学式: C₁₄H₂₀ClN₃O₂
• 分子量: 297.785
• InChiKey: IBKYGWNFZOKKKX-UHFFFAOYSA-N

物化性质

• 沸点：
  401.1±40.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-chloro-5-nitro-benzyl)-4-isopropyl piperazine 在 盐酸 、 tin 、 水 作用下， 反应 1.5h， 以80%的产率得到4-chloro-3-(4-isopropyl-piperazin-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
• 作为产物：
  描述：

  1-异丙基哌嗪 、 2-溴甲基-1-氯-4-硝基苯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以29%的产率得到1-(2-chloro-5-nitro-benzyl)-4-isopropyl piperazine
  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

文献信息

• US7531553B2
  申请人：——

  公开号：US7531553B2

  公开（公告）日：2009-05-12