chloromethyl 2-ethylpentanoate | 1378694-84-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: chloromethyl 2-ethylpentanoate
• 英文别名: Chloromethyl 2-ethylpentanoate
• CAS: 1378694-84-8
• 化学式: C₈H₁₅ClO₂
• 分子量: 178.659
• InChiKey: QAYAUEHMORKGJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  chloromethyl 2-ethylpentanoate 、 [2-(8,9-Dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)ethyl]-phosphonic Acid 在 二异戊胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以56%的产率得到3-{2-[8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl]ethyl}-3-oxido-7-oxo-8-propyl-2,4,6-trioxa-3-phosphaundec-1-yl 2-ethylpentanoate
  参考文献：
  名称：

  Prodrugs of Perzinfotel with Improved Oral Bioavailability

  摘要：

  Previous studies with perzinfotel (1), a potent, selective, competitive NMDA receptor antagonist, showed it to be efficacious in inflammatory and neuropathic pain models. To increase the low oral bioavailability of 1 (3-5%), prodrug derivatives (3a-h) were synthesized and evaluated. The oxymethylene-spaced diphenyl analogue 3a demonstrated good stability at acidic and neutral pH, as well as in simulated gastric fluid. In rat plasma, 3a was rapidly converted to 1 via 2a. Pharmacokinetic Studies indicated that the amount of systemic exposure of 1 produced by a 10 mg/kg oral dose of 3a was 2.5-fold greater than that produced by. a 30 mg/kg oral dose of L Consistent with these results, 3a was significantly more potent and had a longer duration of activity than I following oral administration in a rodent model of inflammatory pain. Taken together, these results demonstrate that an oxymethylene-spaced prodrug approach increased the bioavailability of 1.

  DOI：

  10.1021/jm8011799
• 作为产物：
  描述：

  聚合甲醛 、 Alpha-乙基戊酸 在 zinc(II) chloride 作用下， 生成 chloromethyl 2-ethylpentanoate
  参考文献：
  名称：

  Prodrugs of Perzinfotel with Improved Oral Bioavailability

  摘要：

  Previous studies with perzinfotel (1), a potent, selective, competitive NMDA receptor antagonist, showed it to be efficacious in inflammatory and neuropathic pain models. To increase the low oral bioavailability of 1 (3-5%), prodrug derivatives (3a-h) were synthesized and evaluated. The oxymethylene-spaced diphenyl analogue 3a demonstrated good stability at acidic and neutral pH, as well as in simulated gastric fluid. In rat plasma, 3a was rapidly converted to 1 via 2a. Pharmacokinetic Studies indicated that the amount of systemic exposure of 1 produced by a 10 mg/kg oral dose of 3a was 2.5-fold greater than that produced by. a 30 mg/kg oral dose of L Consistent with these results, 3a was significantly more potent and had a longer duration of activity than I following oral administration in a rodent model of inflammatory pain. Taken together, these results demonstrate that an oxymethylene-spaced prodrug approach increased the bioavailability of 1.

  DOI：

  10.1021/jm8011799