N-(7-chloro-4-quinolinyl)-N'-methyl-1,3-propanediamine

• 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: N-(7-chloro-4-quinolinyl)-N'-methyl-1,3-propanediamine
• 英文别名: {3-[(7-chloroquinolin-4-yl)amino] propyl}(methyl)amine；N-(7-chloroquinolin-4-yl)-3-methylpropane-1,3-diamine；{3-[(7-chloroquinolin-4-yl)amino]propyl}(methyl)amine；MB1_A_020500A-3；TCMDC-125233；MMV020500；N'-(7-chloroquinolin-4-yl)-N-methylpropane-1,3-diamine
• 化学式: C₁₃H₁₆ClN₃
• mdl: MFCD07628400
• 分子量: 249.743
• InChiKey: DSQFFQFYQVGMPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二茂铁甲醛 、 N-(7-chloro-4-quinolinyl)-N'-methyl-1,3-propanediamine 在 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以70%的产率得到{3-[(7-chloroquinolin-4-yl)amino]propyl}(ferrocenylmethyl)methylamine
  参考文献：
  名称：

  Synthesis, in vitro antiplasmodial and antiproliferative activities of a series of quinoline–ferrocene hybrids

  摘要：

  Series of quinoline-ferrocene hybrids containing various linkers were synthesized and evaluated for antimalarial and anticancer activities as well as cytotoxicity. The hybrids with rigid linkers were found to be inactive, while those with flexible spacers showed activity against both the D10 and Dd2 strains of Plasmodium falciparum, and demonstrated a good selectivity towards these parasitic cells in comparison with emetine. The hybrid 16, featuring 3-aminopropyl methylamine linker, was the most antimalarial active compound, exhibiting a significantly better potency than chloroquine against the Dd2 strain (IC50 = 0.008 vs. 0.148 mu M; 19-fold), and was also found to be significantly more active than the equimolar chloroquine-ferrocene combination (IC50 = 3.7 vs. 41 ng/ml, tenfold) against the Dd2 strain. Anticancer activity screening showed that all the antimalarial active hybrids also exhibited potent cytostatic (GI(50) = 0.6-3.3 mu M) and had good cytotoxic effects (LC50 = 6-8 mu M) against all three cancer cell lines. The hybrid 11 possessing 1,4-butanediamine linker was distinctively the most antiproliferative of all. It was found to be more cytostatic (GI(50): 0.7 vs. 5.9 mu M, eightfold) and (LC50: 6.4 vs. 92.6 mu M, 14-fold) more cytotoxic than etoposide against the TK10 (renal) cell line.

  DOI：

  10.1007/s00044-013-0748-4
• 作为产物：
  描述：

  4,7-二氯喹啉 、 3-甲氨基丙胺 生成 N-(7-chloro-4-quinolinyl)-N'-methyl-1,3-propanediamine
  参考文献：
  名称：

  Tarbell et al., Journal of the American Chemical Society, 1946, vol. 68, p. 1218

  摘要：

  DOI：

文献信息

• Tarbell et al., Journal of the American Chemical Society, 1946, vol. 68, p. 1218
  作者：Tarbell et al.

  DOI：——

  日期：——
• Synthetic Antimalarials. The Preparation of Certain 4-Aminoquinolines¹
  作者：Nathan L. Drake、Hugh J. Creech、John A. Garman、Stuart T. Haywood、Richard M. Peck、John O. van Hook、Edward Walton

  DOI：10.1021/ja01211a021

  日期：1946.7
• Synthesis, in vitro antimalarial activity and cytotoxicity of novel 4-aminoquinolinyl-chalcone amides
  作者：Frans J. Smit、David D. N’Da

  DOI：10.1016/j.bmc.2013.12.032

  日期：2014.2

  A series of 4-aminoquinolinyl-chalcone amides 11-19 were synthesized through condensation of carboxylic acid-functionalized chalcone with aminoquinolines, using 1,1'-carbonyldiimidazole as coupling agent. These compounds were screened against the chloroquine sensitive (3D7) and chloroquine resistant (W2) strains of Plasmodium falciparum. Their cytotoxicity towards the WI-38 cell line of normal human fetal lung fibroblast was determined. All compounds were found active, with IC50 values ranging between 0.04-0.5 mu M and 0.07-1.8 mu M against 3D7 and W2, respectively. They demonstrated moderate to high selective activity towards the parasitic cells in the presence of mammalian cells. However, amide 15, featuring the 1,6-diaminohexane linker, despite possessing predicted unfavourable aqueous solubility and absorption properties, was the most active of all the amides tested. It was found to be as potent as CQ against 3D7, while it displayed a two-fold higher activity than CQ against the W2 strain, with good selective antimalarial activity (SI = 435) towards the parasitic cells. During this study, amide 15 was thus identified as the best drug-candidate to for further investigation as a potential drug in search for new, safe and effective antimalarial drugs. (C) 2013 Elsevier Ltd. All rights reserved.
• Kojic acid derived hydroxypyridinone–chloroquine hybrids: Synthesis, crystal structure, antiplasmodial activity and β-haematin inhibition
  作者：Warren Andrew Andayi、Timothy J. Egan、Kelly Chibale

  DOI：10.1016/j.bmcl.2014.06.012

  日期：2014.8

  Aminochloroquinoline-kojic acid hybrids were synthesized and evaluated for p-haematin inhibition and antiplasmodial activity against drug resistant (K1) and sensitive (3D7) strains of Plasmodium falciparum. Compound 7j was the most potent compound in both strains (IC503D7 = 0.004 mu M; IC50K1 = 0.03 mu M) and had the best beta-haematin inhibition activity (0.07 IC50 equiv vs 1.91 IC50 equiv for chloroquine). One compound 8c was found to be equipotent in both strains (IC50 = 0.04 mu M). (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis, in vitro antiplasmodial and antiproliferative activities of a series of quinoline–ferrocene hybrids
  作者：David D. N’Da、Peter J. Smith

  DOI：10.1007/s00044-013-0748-4

  日期：2014.3

  Series of quinoline-ferrocene hybrids containing various linkers were synthesized and evaluated for antimalarial and anticancer activities as well as cytotoxicity. The hybrids with rigid linkers were found to be inactive, while those with flexible spacers showed activity against both the D10 and Dd2 strains of Plasmodium falciparum, and demonstrated a good selectivity towards these parasitic cells in comparison with emetine. The hybrid 16, featuring 3-aminopropyl methylamine linker, was the most antimalarial active compound, exhibiting a significantly better potency than chloroquine against the Dd2 strain (IC50 = 0.008 vs. 0.148 mu M; 19-fold), and was also found to be significantly more active than the equimolar chloroquine-ferrocene combination (IC50 = 3.7 vs. 41 ng/ml, tenfold) against the Dd2 strain. Anticancer activity screening showed that all the antimalarial active hybrids also exhibited potent cytostatic (GI(50) = 0.6-3.3 mu M) and had good cytotoxic effects (LC50 = 6-8 mu M) against all three cancer cell lines. The hybrid 11 possessing 1,4-butanediamine linker was distinctively the most antiproliferative of all. It was found to be more cytostatic (GI(50): 0.7 vs. 5.9 mu M, eightfold) and (LC50: 6.4 vs. 92.6 mu M, 14-fold) more cytotoxic than etoposide against the TK10 (renal) cell line.