N-(9,10-dihydro-9,10-dioxo-1-anthracenyl)-3-<4-(3-hydroxypropyl)piperazin-1-yl>propanamide hydrochloride | 112764-15-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(9,10-dihydro-9,10-dioxo-1-anthracenyl)-3-<4-(3-hydroxypropyl)piperazin-1-yl>propanamide hydrochloride
• 英文别名: N-(9,10-dihydro-9,10-dioxo-1-anthracenyl)-3-[4-(3-hydroxypropyl)piperazin-1-yl]propanamide hydrochloride；N-(9,10-dioxoanthracen-1-yl)-3-[4-(3-hydroxypropyl)piperazin-1-yl]propanamide;hydron;chloride
• CAS: 112764-15-5
• 化学式: C₂₄H₂₇N₃O₄*ClH
• 分子量: 457.957
• InChiKey: FEXBQVPWKFAOOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  90
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  氨基-9,10-蒽二酮 在 吡啶 、 盐酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 9.0h， 生成 N-(9,10-dihydro-9,10-dioxo-1-anthracenyl)-3-<4-(3-hydroxypropyl)piperazin-1-yl>propanamide hydrochloride
  参考文献：
  名称：

  Synthesis, molecular modeling, DNA binding, and antitumor properties of some substituted amidoanthraquinones

  摘要：

  A series of 1- and 1,4-substituted amidoanthraquinones have been prepared, with side chains possessing basic nitrogen atoms. Computer modeling and energy calculations have shown that all eight compounds can bind intercalatively to DNA and that there are significant differences in the additional nonbonded and electrostatic interactions possible at the DNA binding site. Solution DNA binding and closed-circular DNA unwinding studies confirmed intercalative interactions, and the predicted differences in strength of interactions between mono- and disubstituted compounds were found. All compounds were modestly cytotoxic to L1210 cells in culture. In vivo activity against L1210 and S180 tumors was not found for the monosubstituted compounds, whereas the four disubstituted ones had varying levels of measurable, though low, activity.

  DOI：

  10.1021/jm00399a028

文献信息

• COLLIER, DAVID A.;NEIDLE, STEPHEN, J. MED. CHEM., 31,(1988) N 4, 847-857
  作者：COLLIER, DAVID A.、NEIDLE, STEPHEN

  DOI：——

  日期：——
• Synthesis, molecular modeling, DNA binding, and antitumor properties of some substituted amidoanthraquinones
  作者：David A. Collier、Stephen Neidle

  DOI：10.1021/jm00399a028

  日期：1988.4

  A series of 1- and 1,4-substituted amidoanthraquinones have been prepared, with side chains possessing basic nitrogen atoms. Computer modeling and energy calculations have shown that all eight compounds can bind intercalatively to DNA and that there are significant differences in the additional nonbonded and electrostatic interactions possible at the DNA binding site. Solution DNA binding and closed-circular DNA unwinding studies confirmed intercalative interactions, and the predicted differences in strength of interactions between mono- and disubstituted compounds were found. All compounds were modestly cytotoxic to L1210 cells in culture. In vivo activity against L1210 and S180 tumors was not found for the monosubstituted compounds, whereas the four disubstituted ones had varying levels of measurable, though low, activity.