methyl 2-(2-fluoro-4-nitrobenzamido)-3-methylbutanoate | 1187657-03-9

• 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: methyl 2-(2-fluoro-4-nitrobenzamido)-3-methylbutanoate
• 英文别名: methyl (2S)-2-[(2-fluoro-4-nitrobenzoyl)amino]-3-methylbutanoate
• CAS: 1187657-03-9
• 化学式: C₁₃H₁₅FN₂O₅
• 分子量: 298.271
• InChiKey: AKGKPLZKFJMCLS-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-fluoro-4-nitrobenzamido)-3-methylbutanoate 在 lithium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以85%的产率得到2-(2-fluoro-4-nitrobenzamido)-3-methylbutanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of novel F-18 labeled fluoroarylvaline derivatives: Potential PET imaging agents for tumor detection

  摘要：

  Two F-18 labeled fluoroarylvaline derivatives, methyl 2-(2-[F-18]fluoro-4-nitrobenzamido)-3-methylbutanoate ([F-18]1, [F-18]MFNBMB) and its corresponding acid 2-(2-[F-18]fluoro-4-nitrobenzamido)-3-methylbutanoic acid ([F-18]2, [F-18]FNBMBA), have been designed and synthesized, respectively, by our team. Meanwhile, we research on their biodistributions in mice model bearing S 180 tumor. Furthermore, we also carried out the biological evaluations of 2-[F-18]fluorodeoxyglucose ([F-18]FDG) and O-2-[18F]fluoroethyl- L-tyrosine (L-[18F]FET) in the same model for comparison with our targeting molecules [F-18]1 and [F-18]2. Excitingly, the tumor/blood (T/Bl) and tumor/brain (T/Br) ratios were 2.91, 7.06 at 30 min, 3.44, 5.61 at 60 min post injection for [F-18]1, 2.32, 13.30 for [F-18]2 at 30 min post injection, which were obviously superior to [F-18] FDG and L-[F-18] FET in the same model and demonstrated that [F-18]1 and [F-18]2, especially [F-18]2, were potential PET imaging agents for tumor detection. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.027
• 作为产物：
  描述：

  methyl (2S)-2-[(2,4-dinitrobenzoyl)amino]-3-methylbutanoate 在 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以66%的产率得到methyl 2-(2-fluoro-4-nitrobenzamido)-3-methylbutanoate
  参考文献：
  名称：

  Synthesis and evaluation of novel F-18 labeled fluoroarylvaline derivatives: Potential PET imaging agents for tumor detection

  摘要：

  Two F-18 labeled fluoroarylvaline derivatives, methyl 2-(2-[F-18]fluoro-4-nitrobenzamido)-3-methylbutanoate ([F-18]1, [F-18]MFNBMB) and its corresponding acid 2-(2-[F-18]fluoro-4-nitrobenzamido)-3-methylbutanoic acid ([F-18]2, [F-18]FNBMBA), have been designed and synthesized, respectively, by our team. Meanwhile, we research on their biodistributions in mice model bearing S 180 tumor. Furthermore, we also carried out the biological evaluations of 2-[F-18]fluorodeoxyglucose ([F-18]FDG) and O-2-[18F]fluoroethyl- L-tyrosine (L-[18F]FET) in the same model for comparison with our targeting molecules [F-18]1 and [F-18]2. Excitingly, the tumor/blood (T/Bl) and tumor/brain (T/Br) ratios were 2.91, 7.06 at 30 min, 3.44, 5.61 at 60 min post injection for [F-18]1, 2.32, 13.30 for [F-18]2 at 30 min post injection, which were obviously superior to [F-18] FDG and L-[F-18] FET in the same model and demonstrated that [F-18]1 and [F-18]2, especially [F-18]2, were potential PET imaging agents for tumor detection. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.027

文献信息

• Synthesis and evaluation of novel F-18 labeled fluoroarylvaline derivatives: Potential PET imaging agents for tumor detection
  作者：Yali Qiao、Yong He、Shuting Zhang、Guixia Li、Hang Liu、Jingli Xu、Xiao Wang、Chuanmin Qi、Cheng Peng

  DOI：10.1016/j.bmcl.2009.03.027

  日期：2009.8

  Two F-18 labeled fluoroarylvaline derivatives, methyl 2-(2-[F-18]fluoro-4-nitrobenzamido)-3-methylbutanoate ([F-18]1, [F-18]MFNBMB) and its corresponding acid 2-(2-[F-18]fluoro-4-nitrobenzamido)-3-methylbutanoic acid ([F-18]2, [F-18]FNBMBA), have been designed and synthesized, respectively, by our team. Meanwhile, we research on their biodistributions in mice model bearing S 180 tumor. Furthermore, we also carried out the biological evaluations of 2-[F-18]fluorodeoxyglucose ([F-18]FDG) and O-2-[18F]fluoroethyl- L-tyrosine (L-[18F]FET) in the same model for comparison with our targeting molecules [F-18]1 and [F-18]2. Excitingly, the tumor/blood (T/Bl) and tumor/brain (T/Br) ratios were 2.91, 7.06 at 30 min, 3.44, 5.61 at 60 min post injection for [F-18]1, 2.32, 13.30 for [F-18]2 at 30 min post injection, which were obviously superior to [F-18] FDG and L-[F-18] FET in the same model and demonstrated that [F-18]1 and [F-18]2, especially [F-18]2, were potential PET imaging agents for tumor detection. (C) 2009 Elsevier Ltd. All rights reserved.