1-aminoanthraquinone-1-carbonitrile | 411241-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-aminoanthraquinone-1-carbonitrile
• 英文别名: 8-Amino-9,10-dioxoanthracene-1-carbonitrile
• CAS: 411241-54-8
• 化学式: C₁₅H₈N₂O₂
• 分子量: 248.241
• InChiKey: GCJPNIXXFUUXLG-UHFFFAOYSA-N

物化性质

• 熔点：
  263-265 °C(Solv: acetic acid (64-19-7))
• 沸点：
  547.6±50.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-aminoanthraquinone-1-carbonitrile 在 硫酸 作用下， 以 水 为溶剂， 反应 3.0h， 以57%的产率得到1-aminoanthraquinone-1-carboxylic acid
  参考文献：
  名称：

  Synthesis and cytotoxic activity of N-[(alkylamino)alkyl]carboxamide derivatives of 7-oxo-7H-benz[de]anthracene, 7-oxo-7H-naphtho[1,2,3-de]quinoline, and 7-oxo-7H-benzo[e]perimidine

  摘要：

  7-Oxo-7H-naphtho[1,2,3-de]quinoline-11-carboxamides and analogues were prepared and evaluated for in vitro and in vivo antitumor activity. Chromophore variations included 'deaza' (7-oxo-7H-benz[de]anthracene) and 'diaza' (7-oxo-7H-benzo[e]perimidine) analogues, and side chain variations included chiral a-methyl compounds. The naphthoquinolines were the most cytotoxic, with IC50 values of 5-20 nM, and showed the strongest DNA binding, with high selectivity for G-C rich DNA. The chiral a-methyl analogues were 10-20-fold more cytotoxic than the parent des-methyl compound. Both enantiomers provided substantial growth delays against s.c. colon 38 tumors in mice, with the R-enantiomer more active than the S (tumor growth delays of >35 and 12 days, respectively). 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.033
• 作为产物：
  描述：

  1-氨基-8-氯蒽-9,10-二酮 、 氰化亚铜 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以80%的产率得到1-aminoanthraquinone-1-carbonitrile
  参考文献：
  名称：

  Synthesis and cytotoxic activity of N-[(alkylamino)alkyl]carboxamide derivatives of 7-oxo-7H-benz[de]anthracene, 7-oxo-7H-naphtho[1,2,3-de]quinoline, and 7-oxo-7H-benzo[e]perimidine

  摘要：

  7-Oxo-7H-naphtho[1,2,3-de]quinoline-11-carboxamides and analogues were prepared and evaluated for in vitro and in vivo antitumor activity. Chromophore variations included 'deaza' (7-oxo-7H-benz[de]anthracene) and 'diaza' (7-oxo-7H-benzo[e]perimidine) analogues, and side chain variations included chiral a-methyl compounds. The naphthoquinolines were the most cytotoxic, with IC50 values of 5-20 nM, and showed the strongest DNA binding, with high selectivity for G-C rich DNA. The chiral a-methyl analogues were 10-20-fold more cytotoxic than the parent des-methyl compound. Both enantiomers provided substantial growth delays against s.c. colon 38 tumors in mice, with the R-enantiomer more active than the S (tumor growth delays of >35 and 12 days, respectively). 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.033