1-amino-4-(p-carbomethoxyphenyl)-2-hexanone picrate | 102152-82-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-amino-4-(p-carbomethoxyphenyl)-2-hexanone picrate
• 英文别名: 1-Amino-4-p-carbomethoxyphenyl-2-hexanone Picrate；methyl 4-(6-amino-5-oxohexan-3-yl)benzoate;2,4,6-trinitrophenol
• CAS: 102152-82-9
• 化学式: C₆H₃N₃O₇*C₁₄H₁₉NO₃
• 分子量: 478.415
• InChiKey: XDFLIOKOAFLGGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  227
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  盐酸氨基脲 、 1-amino-4-(p-carbomethoxyphenyl)-2-hexanone picrate 以 乙醇 、 水 为溶剂， 反应 90.0h， 以71%的产率得到1-amino-4-(p-carbomethoxyphenyl)-2-hexanone semicarbazone picrate
  参考文献：
  名称：

  Synthesis and biological activity of resolved carbon-10 diastereomers of 10-methyl- and 10-ethyl-10-deazaminopterin

  摘要：

  Synthesis and evaluation of the antitumor drugs 10-methyl- and 10-ethyl-10-deazaminopterin (15a,b) were previously reported for the diastereomeric mixtures, lacking resolution at the C-10 position. In order to assess biological properties of the individual diastereomers, the C-10 isomers of 4-amino-4-deoxy-10-methyl- and 10-ethyl-10-deazapteroic acids (13a,b) were prepared by total synthesis. Coupling with L-glutamate afforded the appropriate diastereomers of the title compounds. Biochemical, transport, and cell growth inhibitory properties in L1210 cells and folate-dependent bacteria were measured. Differences were generally less than 2-fold between diastereomeric pairs, but a factor of 3 was noted for d,L-15b vs. l,L-15b in inhibition of DHFR from L1210 cells and in cytotoxicity toward L1210 cells. An in vivo comparison of the isomers of 15b with racemic compound against L1210 in mice did not show a significant efficacy difference (ILS) among the compounds. However, d,L-15b showed an acute toxicity about 2.5 times that of l,L-15b.

  DOI：

  10.1021/jm00156a026

文献信息

• US4746659A
  申请人：——

  公开号：US4746659A

  公开（公告）日：1988-05-24