(S)-2-(7-chloroquinolin-4-ylamino)-3-phenylpropanoic acid | 1616683-71-6

• 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: (S)-2-(7-chloroquinolin-4-ylamino)-3-phenylpropanoic acid
• 英文别名: (2S)-2-[(7-chloroquinolin-4-yl)amino]-3-phenylpropanoic acid
• CAS: 1616683-71-6
• 化学式: C₁₈H₁₅ClN₂O₂
• 分子量: 326.782
• InChiKey: FEZMSAPAQLRMNO-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(7-chloroquinolin-4-ylamino)-3-phenylpropanoic acid 在 4-二甲氨基吡啶 、 potassium tert-butylate 、 二异丁基氢化铝 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 9.0h， 生成 (E)-4-((7-chloroquinolin-4-yl)amino)-N-methyl-5-phenylpent-2-enamide
  参考文献：
  名称：

  페닐알라닌-클로로퀸 유도체 화합물을 유효성분으로 함유하는 말라리아 감염 질환의 예방 또는 치료용 조성물

  摘要：

  This invention provides an antimalarial agent containing a phenylalanine-chloroquine derivative compound with a novel structure represented by the general formula (I) or a pharmacologically acceptable salt thereof as an active ingredient for the treatment and prevention of malaria infection diseases. Through in vitro antimalarial efficacy screening using Plasmodium falciparum as the target for the novel phenylalanine-chloroquine derivative compounds of the present invention (Experimental Example 1), and animal experiments using malaria-infected mice (Experimental Example 2), it was confirmed that the antimalarial activity of the novel compounds is excellent, thus providing an antimalarial agent containing a phenylalanine-chloroquine derivative compound with a novel structure or a pharmacologically acceptable salt thereof as an effective ingredient.

  公开号：

  KR20180071069A
• 作为产物：
  描述：

  4,7-二氯喹啉 、 L-苯丙氨酸 以 苯酚 为溶剂， 生成 (S)-2-(7-chloroquinolin-4-ylamino)-3-phenylpropanoic acid
  参考文献：
  名称：

  一些双喹啉类药物对氯喹抗性菌株的设计，合成及体外抗疟原虫活性。

  摘要：

  一系列新的双喹啉化合物，包括N1-（7-氯喹啉-4-基）乙烷-1，2-二胺和7-氯-N-（2-（哌嗪-1-基）乙基）喹啉-4-胺描述了含有含有各种氨基酸的7-氯-4-氨基喹啉的衍生物。我们已经在体外对化合物对恶性疟原虫的氯喹敏感（3D7）和氯喹抗性（K1）菌株进行了生物评估。在该系列中，化合物4和7与氯喹（CQ; IC50 = 0.255 +/- 0.049 mum）相比，对K1菌株表现出1.8倍和10.6倍的优异活性，IC50值分别为0.137 +/- 0.014和0.026 +/-。分别为0.007妈妈。此外，与CQ相比，化合物7还显示出对恶性疟原虫的3D7菌株（IC50 = 0.024 +/- 0.003微米）有希望的活性。该系列中的所有化合物均显示出0.57至4之间的电阻系数。CQ为71，而CQ为51。这些结果表明，作为对氯喹抗性恶性疟原虫有活性的新型抗疟药，可以研究双喹啉类化合物的进一步开发。

  DOI：

  10.1111/cbdd.12914

文献信息

• Antiplasmodial activity of new 4-aminoquinoline derivatives against chloroquine resistant strain
  作者：Manish Sinha、Vasanth R. Dola、Pooja Agarwal、Kumkum Srivastava、Wahajul Haq、Sunil K. Puri、Seturam B. Katti

  DOI：10.1016/j.bmc.2014.05.024

  日期：2014.7

  Emergence and spread of multidrug resistant strains of Plasmodium falciparum has severely limited the antimalarial chemotherapeutic options. In order to overcome the obstacle, a set of new side-chain modified 4-aminoquinolines were synthesized and screened against chloroquine-sensitive (3D7) and chloroquine-resistant (K1) strains of P. falciparum. The key feature of the designed molecules is the use of methylpiperazine linked α, β(3)- and γ-amino acids to generate novel side chain modified 4-aminoquinoline analogues. Among the evaluated compounds, 20c and 30 were found more potent than CQ against K1 and displayed a four-fold and a three-fold higher activity respectively, with a good selectivity index (SI=5846 and 11,350). All synthesized compounds had resistance index between 1.06 and >14.13 as against 47.2 for chloroquine. Biophysical studies suggested that this series of compounds act on heme polymerization target.