1-(ethoxycarbonylmethyl)-2,3-diketo-4-[N-(3,4-dimethoxy)phenyl]amino-5-chloro-7,8-dimethoxypyrido[4,3,2-de]quinoline

• 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: 1-(ethoxycarbonylmethyl)-2,3-diketo-4-[N-(3,4-dimethoxy)phenyl]amino-5-chloro-7,8-dimethoxypyrido[4,3,2-de]quinoline
• 英文别名: ethyl 2-[7-chloro-6-(3,4-dimethoxyanilino)-10,11-dimethoxy-3,4-dioxo-2,8-diazatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaen-2-yl]acetate
• 化学式: C₂₅H₂₄ClN₃O₈
• 分子量: 529.934
• InChiKey: JBKBKNCWJZECDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  125.52
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基苯胺 、 (5-Chloro-7,8-dimethoxy-2,3-dioxo-2,3-dihydro-benzo[ij][2,7]naphthyridin-1-yl)-acetic acid ethyl ester 在 air 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以75%的产率得到1-(ethoxycarbonylmethyl)-2,3-diketo-4-[N-(3,4-dimethoxy)phenyl]amino-5-chloro-7,8-dimethoxypyrido[4,3,2-de]quinoline
  参考文献：
  名称：

  Novel Amination and 1,2-Amino,hydro-Elimination between 2,3-Diketopyrido[4,3,2-de]quinolines and Primary Amino Compounds

  摘要：

  novel amination and 1,2-amino,hydro-elimination reaction occurs between 2,3-diketopyrido[4,3,2-de]quinoline (1, 2) and amino compounds which include alpha-amino acids and peptides which contain a primary amino group. The amino group undergoes nucleophilic addition to the double bond between C3 a and C4 in 2,3 -diketopyrido [4,3,2-de] quinoline to form a 3a,4-dihydro-2,3-diketopyrido[4,3,2-de]quinoline. This dihydro intermediate is immediately oxidized by ambient air to produce the more stable aromatic system, 4-(N-alkyl or aryl)-2,3-diketopyrido[4,3,2-de]quinoline (5-12). In the cases of aliphatic amines bearing a beta-proton in THF or chloroform, this 4-(N-alkyl)-2,3-diketopyrido-[4,3,2-de]quinoline undergoes a 1,2-amino,hydro-elimination reaction to eliminate an alkene and produce the 4-amino-2,3-diketopyrido[4,3,2-de]quinol (13, 14). In the cases of alpha-amino acids in aqueous solution, the 4-(N-alkyl)-2,3-diketopyrido[4,3,2-de]quinoline undergoes an amino-transferring reaction, via a mechanism similar to the action of pyridoxal, to form the 4-amino-2,3-diketopyrido[4,3,2-de]quinoline (13) and the alpha-keto acid. 2,3-Diketopyrido[4,3,2-de]quinoline (1) can also react with the peptide which contains a primary amino group to form the 2,3-diketopyrido[4, 3,2-de]quinoline- peptide conjugate. This novel amination- elimination reaction may underlie the marked cytotoxic potency of the 2,3-diketopyrido[4,3,2-de]quinolines (1 and 2). As inorganic amino compounds, hydroxylamine and hydrazine can also undergo the nucleophilic addition to 2,3-diketopyrido[4,3,2-de]quinoline (1, 2) to produce 4-amino-2,3-diketopyrido[4,3,2-de]quinol (13, 14) which. includes a elimination reaction between C4 and alpha-nitrogen.

  DOI：

  10.1021/jo9910132

文献信息

• Novel Amination and 1,2-Amino,hydro-Elimination between 2,3-Diketopyrido[4,3,2-<i>d</i><i>e</i>]quinolines and Primary Amino Compounds
  作者：Qizhu Ding、J. William Lown

  DOI：10.1021/jo9910132

  日期：1999.10.1

  novel amination and 1,2-amino,hydro-elimination reaction occurs between 2,3-diketopyrido[4,3,2-de]quinoline (1, 2) and amino compounds which include alpha-amino acids and peptides which contain a primary amino group. The amino group undergoes nucleophilic addition to the double bond between C3 a and C4 in 2,3 -diketopyrido [4,3,2-de] quinoline to form a 3a,4-dihydro-2,3-diketopyrido[4,3,2-de]quinoline. This dihydro intermediate is immediately oxidized by ambient air to produce the more stable aromatic system, 4-(N-alkyl or aryl)-2,3-diketopyrido[4,3,2-de]quinoline (5-12). In the cases of aliphatic amines bearing a beta-proton in THF or chloroform, this 4-(N-alkyl)-2,3-diketopyrido-[4,3,2-de]quinoline undergoes a 1,2-amino,hydro-elimination reaction to eliminate an alkene and produce the 4-amino-2,3-diketopyrido[4,3,2-de]quinol (13, 14). In the cases of alpha-amino acids in aqueous solution, the 4-(N-alkyl)-2,3-diketopyrido[4,3,2-de]quinoline undergoes an amino-transferring reaction, via a mechanism similar to the action of pyridoxal, to form the 4-amino-2,3-diketopyrido[4,3,2-de]quinoline (13) and the alpha-keto acid. 2,3-Diketopyrido[4,3,2-de]quinoline (1) can also react with the peptide which contains a primary amino group to form the 2,3-diketopyrido[4, 3,2-de]quinoline- peptide conjugate. This novel amination- elimination reaction may underlie the marked cytotoxic potency of the 2,3-diketopyrido[4,3,2-de]quinolines (1 and 2). As inorganic amino compounds, hydroxylamine and hydrazine can also undergo the nucleophilic addition to 2,3-diketopyrido[4,3,2-de]quinoline (1, 2) to produce 4-amino-2,3-diketopyrido[4,3,2-de]quinol (13, 14) which. includes a elimination reaction between C4 and alpha-nitrogen.