[3-(7-chloro-quinolin-4-ylamino)-propyl]dithiocarbamic acid methyl ester | 1257410-16-4

• 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: [3-(7-chloro-quinolin-4-ylamino)-propyl]dithiocarbamic acid methyl ester
• 英文别名: 3-(7-chloroquinolin-4-ylamino)propyldithiocarbamic acid methyl ester；methyl N-[3-[(7-chloroquinolin-4-yl)amino]propyl]carbamodithioate
• CAS: 1257410-16-4
• 化学式: C₁₄H₁₆ClN₃S₂
• 分子量: 325.886
• InChiKey: YIPLWLPWWXVESQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  94.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [3-(7-chloro-quinolin-4-ylamino)-propyl]dithiocarbamic acid methyl ester 、 1,3-丙二胺 以 甲醇 为溶剂， 反应 24.0h， 以85%的产率得到1-[3-[(7-Chloro-4-quinolyl)amino]propyl]-3-[3-[3-[(7-chloro-4-quinolyl)amino]propylcarbamothioylamino]propyl]thiourea
  参考文献：
  名称：

  Synthesis, characterization, antiparasitic and cytotoxic evaluation of thioureas conjugated to polyamine scaffolds

  摘要：

  A series of mono- and multimeric 4-amino-7-chloroquinoline and ferrocenyl thioureas have been prepared by the reaction of a 7-chloroquinoline methyl ester and a ferrocenylimine methyl ester with various amines. These compounds were characterized using standard spectroscopic and analytical techniques. The compounds were evaluated against the NF54 (CQ-sensitive) and Dd2 (CQ-resistant) strains of Plasmodium falciparum. The quinoline compounds show enhanced activity compared to the ferrocene compounds against this parasite. Compound 5 displays the most promising activity against the NF54 strain. Compounds 5 and 6 are effective at inhibiting beta-hematin formation perhaps due to an increased number of quinoline moieties. The trimeric (12) and tetrameric (13) ferrocenyl compounds also inhibit beta-hematin formation, albeit to a lesser degree compared to the quinoline thioureas. The compounds were also screened against the G3 strain of Trichomonas vaginalis and here the ferrocenecontaining compounds show a slightly higher parasite growth inhibition compared to the quinoline thioureas. The quinoline compounds were also found to be more cytotoxic compared to the ferrocenyl compounds. Compound 6 displays good cytotoxicity against WHCO1 oesophageal cancer cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.004
• 作为产物：
  描述：

  4,7-二氯喹啉 在 potassium hydroxide 作用下， 以 neat (no solvent) 为溶剂， 生成 [3-(7-chloro-quinolin-4-ylamino)-propyl]dithiocarbamic acid methyl ester
  参考文献：
  名称：

  Synthesis, characterization, antiparasitic and cytotoxic evaluation of thioureas conjugated to polyamine scaffolds

  摘要：

  A series of mono- and multimeric 4-amino-7-chloroquinoline and ferrocenyl thioureas have been prepared by the reaction of a 7-chloroquinoline methyl ester and a ferrocenylimine methyl ester with various amines. These compounds were characterized using standard spectroscopic and analytical techniques. The compounds were evaluated against the NF54 (CQ-sensitive) and Dd2 (CQ-resistant) strains of Plasmodium falciparum. The quinoline compounds show enhanced activity compared to the ferrocene compounds against this parasite. Compound 5 displays the most promising activity against the NF54 strain. Compounds 5 and 6 are effective at inhibiting beta-hematin formation perhaps due to an increased number of quinoline moieties. The trimeric (12) and tetrameric (13) ferrocenyl compounds also inhibit beta-hematin formation, albeit to a lesser degree compared to the quinoline thioureas. The compounds were also screened against the G3 strain of Trichomonas vaginalis and here the ferrocenecontaining compounds show a slightly higher parasite growth inhibition compared to the quinoline thioureas. The quinoline compounds were also found to be more cytotoxic compared to the ferrocenyl compounds. Compound 6 displays good cytotoxicity against WHCO1 oesophageal cancer cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.004

文献信息

• 4-Aminoquinoline derived antimalarials: Synthesis, antiplasmodial activity and heme polymerization inhibition studies
  作者：V.R. Solomon、W. Haq、M. Smilkstein、Kumkum Srivastava、Sunil K. Puri、S.B. Katti

  DOI：10.1016/j.ejmech.2010.07.068

  日期：2010.11

  A new series of 4-aminoquinoline derivatives have been synthesized and found to be active against both susceptible and resistant strains of Plasmodium falciparum in vitro. Compound 1-[3-(7-chloro-quinolin-4-ylamino)-propyl]-3-cyclopropyl-thiourea (7) exhibited superior in vitro activity against resistant strains of P. falciparum as compared to chloroquine (CQ). All the compounds showed resistance factor between 0.59 and 4.31 as against 5.05 for CQ. Spectroscopic studies suggested that this class of compounds act on heme polymerization target. (C) 2010 Elsevier Masson SAS. All rights reserved.