6-chloro-2-(isopropylaminomethyl)-4-phenylquinoline-3-carboxylic acid | 1335025-24-5

• 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: 6-chloro-2-(isopropylaminomethyl)-4-phenylquinoline-3-carboxylic acid
• 英文别名: 6-Chloro-4-phenyl-2-[(propan-2-ylamino)methyl]quinoline-3-carboxylic acid
• CAS: 1335025-24-5
• 化学式: C₂₀H₁₉ClN₂O₂
• 分子量: 354.836
• InChiKey: FUXBESXPGCDFIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-5-氯二苯甲酮 在 盐酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 6-chloro-2-(isopropylaminomethyl)-4-phenylquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis, trypanocidal activity and molecular modeling studies of 2-alkylaminomethylquinoline derivatives

  摘要：

  Research and development of new drugs effective in the treatment of Trypanosoma cruzi infections are a real need for the 16 million people infected in the Americas. In a previous work, a quinoline derivative substituted by a 2-piperidylmethyl moiety showed to be active against Chagas disease and was considered a lead compound for further optimization. A series of ten analogous derivatives were tested against epimastigotes as a first approach. In view of their promising results, six of them were evaluated against the blood and intracellular replicative forms of the parasite in humans. Among them, compound 12 which possesses a 6-acetamidohexylamino substituent showed remarkable improvement in activity against epimastigotes, trypomastigotes and amastigotes compared with the structure lead, as well as a good selectivity index for the two parasite stages present in humans. In addition, treatment of infected mice with compound 12 induced a significant reduction in parasitemia compared with non-treated mice. Molecular modeling studies were performed by computational methods in order to elucidate the factors determining these experimental bioactivities. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.035

文献信息

• Synthesis, trypanocidal activity and molecular modeling studies of 2-alkylaminomethylquinoline derivatives
  作者：Gisela C. Muscia、Silvia I. Cazorla、Fernanda M. Frank、Gabriela L. Borosky、Graciela Y. Buldain、Silvia E. Asís、Emilio L. Malchiodi

  DOI：10.1016/j.ejmech.2011.05.035

  日期：2011.9

  Research and development of new drugs effective in the treatment of Trypanosoma cruzi infections are a real need for the 16 million people infected in the Americas. In a previous work, a quinoline derivative substituted by a 2-piperidylmethyl moiety showed to be active against Chagas disease and was considered a lead compound for further optimization. A series of ten analogous derivatives were tested against epimastigotes as a first approach. In view of their promising results, six of them were evaluated against the blood and intracellular replicative forms of the parasite in humans. Among them, compound 12 which possesses a 6-acetamidohexylamino substituent showed remarkable improvement in activity against epimastigotes, trypomastigotes and amastigotes compared with the structure lead, as well as a good selectivity index for the two parasite stages present in humans. In addition, treatment of infected mice with compound 12 induced a significant reduction in parasitemia compared with non-treated mice. Molecular modeling studies were performed by computational methods in order to elucidate the factors determining these experimental bioactivities. (C) 2011 Elsevier Masson SAS. All rights reserved.