(10S,14S)-1-(6-fluoropyridin-3-yl)-1,6,12-trioxo-5-phenyl-2,5,11,13-tetraazahexadecane-10,14,16-tricarboxylic acid

• 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: (10S,14S)-1-(6-fluoropyridin-3-yl)-1,6,12-trioxo-5-phenyl-2,5,11,13-tetraazahexadecane-10,14,16-tricarboxylic acid
• 英文别名: (2~{S})-2-[[(2~{S})-6-[2-[(6-fluoranylpyridin-3-yl)carbonylamino]ethyl-phenyl-amino]-1-oxidanyl-1,6-bis(oxidanylidene)hexan-2-yl]carbamoylamino]pentanedioic acid；(2S)-2-[[(1S)-1-carboxy-5-[N-[2-[(6-fluoropyridine-3-carbonyl)amino]ethyl]anilino]-5-oxopentyl]carbamoylamino]pentanedioic acid
• 化学式: C₂₆H₃₀FN₅O₉
• 分子量: 575.551
• InChiKey: AFDHXMJDHQVEHD-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  215
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  benzyl (2-(phenylamino)ethyl)carbamate 在 palladium on activated charcoal 、 氢气 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 (10S,14S)-1-(6-fluoropyridin-3-yl)-1,6,12-trioxo-5-phenyl-2,5,11,13-tetraazahexadecane-10,14,16-tricarboxylic acid
  参考文献：
  名称：

  2-Aminoadipic Acid–C(O)–Glutamate Based Prostate-Specific Membrane Antigen Ligands for Potential Use as Theranostics

  摘要：

  The design and synthesis of prostate specific membrane antigen (PSMA) ligands derived from 2-aminoadipic acid, a building block that has not previously been used to construct PSMA. ligands, are reported. The effects of both the linker length and of an N-substituent of our PSMA ligands were probed, and X-ray structures of five of these ligands bound to PSMA were obtained. Among the ligands disclosed herein, 13b showed the highest inhibitory activity for PSMA. As ligand 13b can readily be radiolabeled since its fluorine atom is adjacent to the nitrogen atom of its pyridine ring, the use of this and related compounds as theranostics can be pursued.

  DOI：

  10.1021/acsmedchemlett.8b00318