7-chloro-4-(3-methylpiperazin-1-yl)quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 7-chloro-4-(3-methylpiperazin-1-yl)quinoline
• 英文别名: 7-chloro-4-(3-methylpiperazin-1-yl)quinolone
• 化学式: C₁₄H₁₆ClN₃
• mdl: MFCD17083801
• 分子量: 261.754
• InChiKey: CTJTUYHCTCIMPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-chloro-4-(3-methylpiperazin-1-yl)quinoline 、 二茂铁甲醛 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58%的产率得到7-chloro-4-[4-(ferrocenylmethyl)-3-methylpiperazin-1-yl]quinoline
  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 、 2-甲基哌嗪 以 乙醇 为溶剂， 以90 %的产率得到7-chloro-4-(3-methylpiperazin-1-yl)quinoline
  参考文献：
  名称：

  1,3,5-三嗪-喹啉衍生物作为丁酰胆碱酯酶抑制剂的合成、表征、晶体结构和生物学评价

  摘要：

  设计和合成了 16 种新的 1,3,5-三嗪-喹啉衍生物，并作为胆碱酯酶抑制剂进行了评估。1,3,5-三嗪-喹啉衍生物的结构经IR、NMR、HRMS和单晶X射线衍射实验证实。化合物5j具有单斜晶系和P2 1 /c空间群。化合物5k具有单斜晶系和C2/c空间群。合成化合物的胆碱酯酶抑制活性使用比色埃尔曼法测量。化合物5g显示出最好的乙酰胆碱酯酶抑制活性，IC 50值为10.82 μM，丁酰胆碱酯酶抑制活性IC 50值为 0.046 μM。分子对接表明化合物5g可以与丁酰胆碱酯酶的活性位点相互作用。

  DOI：

  10.1016/j.molstruc.2022.134391

文献信息

• [EN] SUBSTITUTED QUINOLINE CCR5 RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR CCR5 A BASE DE QUINOLEINE SUBSTITUES
  申请人：SCHERING AG

  公开号：WO2004002960A1

  公开（公告）日：2004-01-08

  The present invention relates to CCR5 receptor antagonists of formulae (1a) or (1b), enantiomers, diastereomers, salts and solvates thereof wherein R1, R2, R3, R4, R5, and R7 are as defined herein. The invention further includes a method of CCR5-mediated disorders employing such compounds.

  本发明涉及式（1a）或（1b）的CCR5受体拮抗剂，其对映体、二对映体、盐和溶剂合物，其中R1、R2、R3、R4、R5和R7如本文所定义。该发明还包括一种利用这些化合物治疗CCR5介导的疾病的方法。
• Substituted quinoline CCR5 receptor antagonists
  申请人：Schering Aktiengesellschaft

  公开号：US20040072818A1

  公开（公告）日：2004-04-15

  The present invention relates to CCR5 receptor antagonists of formulae (1a) or (1b): 1 enantiomers, diastereomers, salts and solvates thereof wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 7 are as defined herein. The invention further includes a method of CCR5-mediated disorders employing such compounds.

  本发明涉及公式（1a）或（1b）的CCR5受体拮抗剂：1对映体，对异构体，其盐和溶剂化物，其中R1、R2、R3、R4、R5和R7如本文所定义。本发明还包括一种利用这些化合物治疗CCR5介导的疾病的方法。
• SUBSTITUTED QUINOLINE CCR5 RECEPTOR ANTAGONISTS
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP1534681A1

  公开（公告）日：2005-06-01
• US7220856B2
  申请人：——

  公开号：US7220856B2

  公开（公告）日：2007-05-22
• 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.