4-(4-Nitro-9-oxo-9,10-dihydro-acridin-1-ylamino)-butyric acid | 141523-40-2

• 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: 4-(4-Nitro-9-oxo-9,10-dihydro-acridin-1-ylamino)-butyric acid
• 英文别名: 4-[(4-nitro-9-oxo-10H-acridin-1-yl)amino]butanoic acid
• CAS: 141523-40-2
• 化学式: C₁₇H₁₅N₃O₅
• 分子量: 341.323
• InChiKey: PAUMCEHZLHKMSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(4-Nitro-9-oxo-9,10-dihydro-acridin-1-ylamino)-butyric acid 在 platinum(IV) oxide 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 6-O--N-acetylmuramyl-L-alanyl-D-isoglutamine
  参考文献：
  名称：

  Dzierzbicka, Krystyna; Kolodziejczyk, Aleksander; Wysocka-Skrzela, Barbara, Polish Journal of Chemistry, 1991, vol. 65, # 12, p. 2293 - 2294

  摘要：

  DOI：

文献信息

• Synthesis and Antitumor Activity of Conjugates of Muramyldipeptide, Normuramyldipeptide, and Desmuramylpeptides with Acridine/Acridone Derivatives
  作者：Krystyna Dzierzbicka、Aleksander M. Kołodziejczyk、Barbara Wysocka-Skrzela、Andrzej Myśliwski、Danuta Sosnowska

  DOI：10.1021/jm001115g

  日期：2001.10.1

  The synthesis of two groups (Chart 1, types A and B) of conjugates of MDP (muramyldipeptide) and nor-MDP (normurainyldipeptide) with acridine/acridone derivatives and the synthesis of analogues of desmuramylpeptides (Chart 1, types C and D), containing acridine/ acridone derivatives have been described. In type A conjugates, the hydroxyl group at C6 of the sugar moiety was acylated with acridine/acridone N-substituted omega -aminoalkanocarboxylic acids (Scheme 1), whereas the conjugates of type B (Table 2) and three analogues of type C or D (Scheme 2) have an amide bond formed between the carboxylic group of isoglutamine and the amine function of the respective acridine/acridone derivatives. The preliminary screening data indicate that the analogues of groups A, C, and D exhibit small cytotoxic activity, whereas several analogues of type B, 4b, 4c, 4e, 4g, 4h, 4i, and 4l, exhibiting potent in vitro cytotoxic activity against a panel of human cell lines (Table 4), have been selected by the National Cancer Institute (NCI) Evaluation Committee for further testing. Analogues 4b and 4h were active in the in vivo hollow fiber assay (Table 5). Analogue 3a shows an immunostimulating effect on the cytotoxic activity of the NX cells obtained from the spleen of healthy and Ab melanoma bearing animals.