N-Acetyl-10-aminocolchinol | 156878-60-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: N-Acetyl-10-aminocolchinol
• CAS: 156878-60-3
• 化学式: C₂₀H₂₄N₂O₅
• 分子量: 372.421
• InChiKey: AESBSQBWIBBZIF-HNNXBMFYSA-N

物化性质

• 沸点：
  650.8±55.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  103.04
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-Acetyl-10-aminocolchinol 在 三氟乙酸 、 亚硝酸异戊酯 作用下， 以 乙醇 为溶剂， 以40%的产率得到N-Acetyl-10-diazocolchin-9-one
  参考文献：
  名称：

  Potential Photoaffinity Labels for Tubulin. Synthesis and Evaluation of Diazocyclohexadienone and Azide Analogs of Colchicine, Combretastatin, and 3,4,5-Trimethoxybiphenyl

  摘要：

  Analogs of tubulin assembly inhibitors such as colchicine, combretastatin, and 3,4,5-trimethoxybiphenyl which incorporate a 6-diazo-2,4-cyclohexadienone (o-quinone diazide) ring have been synthesized and characterized. The compounds synthesized include 6-diazo-4-(2',3',4'-trimethoxyphenyl)cyclohexa-2,4-dien-1-one and its 3-methyl and 3-ethyl analogs (1a-c), 6-diazo-3-(2,3,4-trimethoxyphenyl)-2,4-cyclohexadien-1-one and its 4-methyl and 4-ethyl derivatives (2a-c), 4-[Z-2-(3',4',5'-trimethoxyphenyl)ethenyl]-6-diazocyclohexa-2,4-dienone (3), 3-[Z-2-(3',4',5'-trimethoxyphenyl)ethenyl]-6-diazocyclohexa-2,4-dien-1-one (4), the corresponding dihydro derivatives (5, 6) and two isomeric diazocyclohexadienones derived from N-acetylcolchinol (7, 8). Compounds in which the cyclohexadienone oxygen is approximately isostructural with carbonyl or hydroxy functions of the parent compounds exhibit good activity in the tubulin assembly inhibition assay. 2'-Alkyl-4'azido-3,4,5-trimethoxy-1,1'-biphenyls also show good activity as tubulin assembly inhibitors.

  DOI：

  10.1021/jo00094a048
• 作为产物：
  描述：

  N-acetylcolchinol 在 盐酸 、 sodium hydroxide 、 sodium dithionite 、 sodium nitrite 作用下， 以 水 、 丙酮 为溶剂， 反应 24.5h， 生成 N-Acetyl-10-aminocolchinol
  参考文献：
  名称：

  Potential Photoaffinity Labels for Tubulin. Synthesis and Evaluation of Diazocyclohexadienone and Azide Analogs of Colchicine, Combretastatin, and 3,4,5-Trimethoxybiphenyl

  摘要：

  Analogs of tubulin assembly inhibitors such as colchicine, combretastatin, and 3,4,5-trimethoxybiphenyl which incorporate a 6-diazo-2,4-cyclohexadienone (o-quinone diazide) ring have been synthesized and characterized. The compounds synthesized include 6-diazo-4-(2',3',4'-trimethoxyphenyl)cyclohexa-2,4-dien-1-one and its 3-methyl and 3-ethyl analogs (1a-c), 6-diazo-3-(2,3,4-trimethoxyphenyl)-2,4-cyclohexadien-1-one and its 4-methyl and 4-ethyl derivatives (2a-c), 4-[Z-2-(3',4',5'-trimethoxyphenyl)ethenyl]-6-diazocyclohexa-2,4-dienone (3), 3-[Z-2-(3',4',5'-trimethoxyphenyl)ethenyl]-6-diazocyclohexa-2,4-dien-1-one (4), the corresponding dihydro derivatives (5, 6) and two isomeric diazocyclohexadienones derived from N-acetylcolchinol (7, 8). Compounds in which the cyclohexadienone oxygen is approximately isostructural with carbonyl or hydroxy functions of the parent compounds exhibit good activity in the tubulin assembly inhibition assay. 2'-Alkyl-4'azido-3,4,5-trimethoxy-1,1'-biphenyls also show good activity as tubulin assembly inhibitors.

  DOI：

  10.1021/jo00094a048