9-oxo-9,10-dihydroacridin-4-yl-acetic acid | 145447-90-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-oxo-9,10-dihydroacridin-4-yl-acetic acid
• 英文别名: (9-Oxo-9,10-dihydroacridin-4-yl)acetic acid；2-(9-oxo-10H-acridin-4-yl)acetic acid
• CAS: 145447-90-1
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: IAUHSHWVUOMMDX-UHFFFAOYSA-N

物化性质

• 沸点：
  494.8±34.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-oxo-9,10-dihydroacridin-4-yl-acetic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以73%的产率得到2H-Pyrrolo[3,2,1-de]acridine-1,6-dione
  参考文献：
  名称：

  Cancer preventive agents, Part 2: Synthesis and evaluation of 2-phenyl-4-quinolone and 9-oxo-9,10-dihydroacridine derivatives as novel antitumor promoters

  摘要：

  2-Phenyl-4-quinolone and 9-oxo-9,10-dihydroacridine derivatives were synthesized and screened as potential antitumor promoters by examining the ability of the compounds to inhibit Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. Interestingly, compounds 14, 15, and 17 showed similar inhibitory effects (89-92%, 66-69%, and 24-29% at 1000, 500, and 100 mol ratio to TPA, respectively) against EBV-EA with potencies comparable to those of glycyrrhetic acid, a known natural antitumor-promoter. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.078
• 作为产物：
  描述：

  2-硝基苯乙酸 在 palladium on activated charcoal copper(l) iodide 、 氢气 、 铜 、 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 9-oxo-9,10-dihydroacridin-4-yl-acetic acid
  参考文献：
  名称：

  Cancer preventive agents, Part 2: Synthesis and evaluation of 2-phenyl-4-quinolone and 9-oxo-9,10-dihydroacridine derivatives as novel antitumor promoters

  摘要：

  2-Phenyl-4-quinolone and 9-oxo-9,10-dihydroacridine derivatives were synthesized and screened as potential antitumor promoters by examining the ability of the compounds to inhibit Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. Interestingly, compounds 14, 15, and 17 showed similar inhibitory effects (89-92%, 66-69%, and 24-29% at 1000, 500, and 100 mol ratio to TPA, respectively) against EBV-EA with potencies comparable to those of glycyrrhetic acid, a known natural antitumor-promoter. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.078

文献信息

• Cancer preventive agents, Part 2: Synthesis and evaluation of 2-phenyl-4-quinolone and 9-oxo-9,10-dihydroacridine derivatives as novel antitumor promoters
  作者：Seikou Nakamura、Mutsuo Kozuka、Kenneth F. Bastow、Harukuni Tokuda、Hoyoku Nishino、Madoka Suzuki、Jin Tatsuzaki、Susan L. Morris Natschke、Sheng-Chu Kuo、Kuo-Hsiung Lee

  DOI：10.1016/j.bmc.2005.04.078

  日期：2005.7

  2-Phenyl-4-quinolone and 9-oxo-9,10-dihydroacridine derivatives were synthesized and screened as potential antitumor promoters by examining the ability of the compounds to inhibit Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. Interestingly, compounds 14, 15, and 17 showed similar inhibitory effects (89-92%, 66-69%, and 24-29% at 1000, 500, and 100 mol ratio to TPA, respectively) against EBV-EA with potencies comparable to those of glycyrrhetic acid, a known natural antitumor-promoter. (c) 2005 Elsevier Ltd. All rights reserved.