ethyl 4-(((S)-1-phenylethyl)amino)pentanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 4-(((S)-1-phenylethyl)amino)pentanoate
• 英文别名: ethyl 4-[[(1S)-1-phenylethyl]amino]pentanoate
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: XBVZCWRUGZEJTH-ABLWVSNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-(((S)-1-phenylethyl)amino)pentanoate 在 四氯化碳 、 palladium on carbon 、 potassium tert-butylate 、 甲酸铵 、 sodium ethanolate 、 三乙酰氧基硼氢化钠 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 35.5h， 生成 5-((S)-6-methyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yloxy)-indole-1-carboxylic acid [5-(1-methylcyclopropyl)-2H-pyrazol-3-yl]amide
  参考文献：
  名称：

  Discovery of Oral VEGFR-2 Inhibitors with Prolonged Ocular Retention That Are Efficacious in Models of Wet Age-Related Macular Degeneration

  摘要：

  The benefit of intravitreal anti-VEGF therapy in treating wet age-related macular degeneration (AMD) is well established. Identification of VEGFR-2 inhibitors with optimal ADME properties for an ocular indication provides opportunities for dosing routes beyond intravitreal injection. We employed a high throughput in vivo screening strategy with rodent models of choroidal neovascularization and iterative compound design to identify VEGFR-2 inhibitors with potential to benefit wet AMD patients. These compounds demonstrate preferential ocular tissue distribution and efficacy after oral administration while minimizing systemic exposure.

  DOI：

  10.1021/acs.jmedchem.5b01227
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 乙酰丙酸乙酯 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 ethyl 4-(((S)-1-phenylethyl)amino)pentanoate
  参考文献：
  名称：

  Discovery of Oral VEGFR-2 Inhibitors with Prolonged Ocular Retention That Are Efficacious in Models of Wet Age-Related Macular Degeneration

  摘要：

  The benefit of intravitreal anti-VEGF therapy in treating wet age-related macular degeneration (AMD) is well established. Identification of VEGFR-2 inhibitors with optimal ADME properties for an ocular indication provides opportunities for dosing routes beyond intravitreal injection. We employed a high throughput in vivo screening strategy with rodent models of choroidal neovascularization and iterative compound design to identify VEGFR-2 inhibitors with potential to benefit wet AMD patients. These compounds demonstrate preferential ocular tissue distribution and efficacy after oral administration while minimizing systemic exposure.

  DOI：

  10.1021/acs.jmedchem.5b01227