N-(3-hydroxypropyl)-9-acridone-4-carboxamide | 487016-10-4

• 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: N-(3-hydroxypropyl)-9-acridone-4-carboxamide
• 英文别名: N-(3-hydroxypropyl)-9-oxo-10H-acridine-4-carboxamide
• CAS: 487016-10-4
• 化学式: C₁₇H₁₆N₂O₃
• 分子量: 296.326
• InChiKey: BDVNUMFAUXGPSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  535.5±50.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-6-(4-tert-butyldimethylsilyloxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoic acid 、 N-(3-hydroxypropyl)-9-acridone-4-carboxamide 在 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  霉酚酸和a啶/ ac啶酮作为潜在免疫抑制剂的酯衍生物的合成及其生物学活性。

  摘要：

  麦考酚酸（MPA）的改良衍生物对于减少这种药物在治疗患者中产生的不良反应的发生率是必不可少的。在这项研究中，MPA与N-（ω-羟烷基）-9-ac啶酮-4-羧酰胺或N-（ω-羟烷基）ac啶-4-羧酰胺偶联后，根据Yamaguchi方案生成相应的酯共轭物。这种酯化作用需要保护MPA中的酚基。设计的结合物显示出比母体MPA更高的体外效价。cr啶衍生物比a啶酮类似物更具活性，MPA和杂环单元之间的烷基接头长度会影响所观察到的细胞毒性。衍生物2b，2d，3a，3b显示出最有希望的免疫抑制活性。

  DOI：

  10.3109/14756366.2015.1077821
• 作为产物：
  描述：

  4-羧基-9-茚酮 、 3-氨基-1-丙醇 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 以80%的产率得到N-(3-hydroxypropyl)-9-acridone-4-carboxamide
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Conjugates of Muramyldipeptide or Normuramyldipeptide with Hydroxyacridine/Acridone Derivatives

  摘要：

  A series of MDP (muramyldipeptide) or nor-MDP (normuramyldipeptide) analogues modified at the C-terminus post of the molecule by a formation of an ester bond between the carboxylic group of isoglutamine and the hydroxyl function of the respective derivatives of 4-carboxamideacridine/9-acridone or 1-nitro-9-hydroxyalkylaminoacridines were synthesized as potential anticancer agents. The compounds O-(1-O-benzyl-N-acetyl-muramyl-L-alanyl-D-gamma-isoglutaminyl)-9-(ethylamino)-1-nitroacridine ester 3j and O-(1-O-benzyl-N-acetyl-muramyl-L-alanyl-D-gamma-isoglutaminyl)-9-propylamino-l-nitroacridine ester 3k exhibited high in vitro cytotoxic activity against a panel of human cell lines, prostate cancer and AIDS-related lymphoma (ARL). Analogue 3j was also active in vivo in the hollow fiber assay. Antitumor activity of both compounds were tested in vivo against difference human tumor xenograft, but only analogue 3k showed in vivo activity against se UACC-62 melanoma in mice.

  DOI：

  10.1021/jm020991m

文献信息

• Synthesis and Antitumor Activity of Conjugates of Muramyldipeptide or Normuramyldipeptide with Hydroxyacridine/Acridone Derivatives
  作者：Krystyna Dzierzbicka、Aleksander M. Kołodziejczyk

  DOI：10.1021/jm020991m

  日期：2003.1.1

  A series of MDP (muramyldipeptide) or nor-MDP (normuramyldipeptide) analogues modified at the C-terminus post of the molecule by a formation of an ester bond between the carboxylic group of isoglutamine and the hydroxyl function of the respective derivatives of 4-carboxamideacridine/9-acridone or 1-nitro-9-hydroxyalkylaminoacridines were synthesized as potential anticancer agents. The compounds O-(1-O-benzyl-N-acetyl-muramyl-L-alanyl-D-gamma-isoglutaminyl)-9-(ethylamino)-1-nitroacridine ester 3j and O-(1-O-benzyl-N-acetyl-muramyl-L-alanyl-D-gamma-isoglutaminyl)-9-propylamino-l-nitroacridine ester 3k exhibited high in vitro cytotoxic activity against a panel of human cell lines, prostate cancer and AIDS-related lymphoma (ARL). Analogue 3j was also active in vivo in the hollow fiber assay. Antitumor activity of both compounds were tested in vivo against difference human tumor xenograft, but only analogue 3k showed in vivo activity against se UACC-62 melanoma in mice.
• Synthesis and biological activity of ester derivatives of mycophenolic acid and acridines/acridones as potential immunosuppressive agents
  作者：Grzegorz Cholewinski、Dorota Iwaszkiewicz-Grzes、Piotr Trzonkowski、Krystyna Dzierzbicka

  DOI：10.3109/14756366.2015.1077821

  日期：2016.11.1

  Improved derivatives of mycophenolic acid (MPA) are necessary to reduce the frequency of adverse effects, this drug exerts in treated patients. In this study, MPA was coupled with N-(ω-hydroxyalkyl)-9-acridone-4-carboxamides or N-(ω-hydroxyalkyl)acridine-4-carboxamides to give respective ester conjugates upon Yamaguchi protocol. This esterification required protection of phenol group in MPA. Designed

  麦考酚酸（MPA）的改良衍生物对于减少这种药物在治疗患者中产生的不良反应的发生率是必不可少的。在这项研究中，MPA与N-（ω-羟烷基）-9-ac啶酮-4-羧酰胺或N-（ω-羟烷基）ac啶-4-羧酰胺偶联后，根据Yamaguchi方案生成相应的酯共轭物。这种酯化作用需要保护MPA中的酚基。设计的结合物显示出比母体MPA更高的体外效价。cr啶衍生物比a啶酮类似物更具活性，MPA和杂环单元之间的烷基接头长度会影响所观察到的细胞毒性。衍生物2b，2d，3a，3b显示出最有希望的免疫抑制活性。