2'-fluoroaminopterin di-tert-butyl ester | 85803-30-1

• 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: 2'-fluoroaminopterin di-tert-butyl ester
• CAS: 85803-30-1
• 化学式: C₂₇H₃₅FN₈O₅
• 分子量: 570.624
• InChiKey: AKFBDXJDGZGKSK-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  197.33
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2'-fluoroaminopterin di-tert-butyl ester 在 三氟乙酸 作用下， 反应 2.0h， 生成 2'-fluoroaminopterin
  参考文献：
  名称：

  Novel fluorinated antifolates. Enzyme inhibition and cytotoxicity studies on 2'- and 3'-fluoroaminopterin

  摘要：

  Two novel analogues of aminopterin with a single fluorine substitution in the 2' (compound 8) or in the 3' (compound 9) position of the p-aminobenzoyl group were synthesized and evaluated as inhibitors of dihydrofolate reductase from two bacterial species and from human HeLa cells. The 2'-fluoro compound was bound essentially the same as aminopterin itself, while the 3'-fluoro derivative bound two- to threefold more tightly in all cases. UV spectral shifts indicated normal binding of the pteridine. Cytotoxicity studies against mouse leukemia L1210 cells and the human stomach cancer line HuTu80 indicated equivalent toxicity of the parent drug with the 2'-fluoro analogue. 3'-Fluoroaminopterin was, however, twice as toxic as aminopterin to both cell lines.

  DOI：

  10.1021/jm00362a019
• 作为产物：
  描述：

  2-氟-4-硝基苯甲酰氯 在 platinum(IV) oxide Proton Sponge 、 异丁酰胺 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 85.0 ℃ 、101.33 kPa 条件下， 反应 19.0h， 生成 2'-fluoroaminopterin di-tert-butyl ester
  参考文献：
  名称：

  Novel fluorinated antifolates. Enzyme inhibition and cytotoxicity studies on 2'- and 3'-fluoroaminopterin

  摘要：

  Two novel analogues of aminopterin with a single fluorine substitution in the 2' (compound 8) or in the 3' (compound 9) position of the p-aminobenzoyl group were synthesized and evaluated as inhibitors of dihydrofolate reductase from two bacterial species and from human HeLa cells. The 2'-fluoro compound was bound essentially the same as aminopterin itself, while the 3'-fluoro derivative bound two- to threefold more tightly in all cases. UV spectral shifts indicated normal binding of the pteridine. Cytotoxicity studies against mouse leukemia L1210 cells and the human stomach cancer line HuTu80 indicated equivalent toxicity of the parent drug with the 2'-fluoro analogue. 3'-Fluoroaminopterin was, however, twice as toxic as aminopterin to both cell lines.

  DOI：

  10.1021/jm00362a019