1-alanyl-3-{4-[(6-methoxyquinolin-8-yl)amino]pentyl}-2,2-dimethylimidazolidin-4-one | 1056898-61-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-alanyl-3-{4-[(6-methoxyquinolin-8-yl)amino]pentyl}-2,2-dimethylimidazolidin-4-one
• 英文别名: 1-glycyl-3-{4-[(6-methoxyquinolin-8-yl)amino]pentyl}-2,2-dimethylimidazolidin-4-one；1-[(2S)-2-aminopropanoyl]-3-[4-[(6-methoxy-8-quinolyl)amino]pentyl]-2,2-dimethyl-imidazolidin-4-one；1-[(2S)-2-aminopropanoyl]-3-[4-[(6-methoxyquinolin-8-yl)amino]pentyl]-2,2-dimethylimidazolidin-4-one
• CAS: 1056898-61-3
• 化学式: C₂₃H₃₃N₅O₃
• 分子量: 427.547
• InChiKey: XHBFICJERBKPGW-LYKKTTPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-[(N-tert-butyloxycarbonyl)alanyl]-3-{4-[(6-methoxyquinolin-8-yl)amino]pentyl}-2,2-dimethylimidazolidin-4-one 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以93%的产率得到1-alanyl-3-{4-[(6-methoxyquinolin-8-yl)amino]pentyl}-2,2-dimethylimidazolidin-4-one
  参考文献：
  名称：

  伯氨喹的咪唑啉丁-4-酮拟肽衍生物：合成和抗疟活性。

  摘要：

  描述了在与母体药物偶联的二肽主链的C末端含有五元环的伯氨喹的咪唑烷二-4-酮衍生物的合成。这些拟肽衍生物对抗氯喹的恶性疟原虫菌株具有活性，并抑制了伯氏疟原虫的孢子周期的发展，影响了蚊子中肠内卵囊的出现。由于N（1）的酰化作用，新型的咪唑烷基-4-酮在人血浆和pH 7.4缓冲液中都极为稳定。因此，衍生自二肽基8-氨基喹啉的“内部”咪唑啉丁-4-酮代表了抗疟疾结构-活性关系中的一个新条目。

  DOI：

  10.1016/j.bmcl.2008.05.076

文献信息

• Anti-tumoral activity of imidazoquines, a new class of antimalarials derived from primaquine
  作者：Iva Fernandes、Nuno Vale、Victor de Freitas、Rui Moreira、Nuno Mateus、Paula Gomes

  DOI：10.1016/j.bmcl.2009.10.081

  日期：2009.12

  The growth inhibitory activity of imidazoquines, antimalarial imidazolidin-4-ones derived from primaquine, on human cancer cell lines HT-29, Caco-2, and MCF-7 has been evaluated. Primaquine, N-dipeptidyl-primaquine derivatives, and other quinolines have been included in the study for comparison purposes. Primaquine and some of its derivatives were significantly active against the MCF-7 human breast cancer cell line, so these compounds might represent useful leads targeted at the development of novel specific agents against breast cancer. Conversely, all compounds were generally inactive against HT-29, with only one of the imidazoquines having IC50 below 50 mu M. Activities against the Caco-2 cell line were modest and did not follow any defined trend. (C) 2009 Elsevier Ltd. All rights reserved.