7-chloro-4-(4-methylpiperazin-1-yl)quinoline | 84594-63-8

• 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-(4-methylpiperazin-1-yl)quinoline
• 英文别名: AI-204/31700051
• CAS: 84594-63-8
• 化学式: C₁₄H₁₆ClN₃
• mdl: MFCD02325516
• 分子量: 261.754
• InChiKey: DYRPMOPVNODEGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  19.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-甲基哌嗪 、 7-氯-4-苯氧基喹啉盐酸盐 反应 3.0h， 以75%的产率得到7-chloro-4-(4-methylpiperazin-1-yl)quinoline
  参考文献：
  名称：

  Dann; Steuding; Lisson, Arzneimittel-Forschung/Drug Research, 1982, vol. 32, # 10, p. 1219 - 1223

  摘要：

  DOI：

文献信息

• Solvent- and chromatography-free amination of π-deficient nitrogen heterocycles under microwave irradiation. A fast, efficient and green route to 9-aminoacridines, 4-aminoquinolines and 4-aminoquinazolines and its application to the synthesis of the drugs amsacrine and bistacrine
  作者：Matteo Staderini、Nieves Cabezas、Maria Laura Bolognesi、J. Carlos Menéndez

  DOI：10.1016/j.tet.2012.11.083

  日期：2013.1

  very broad scope in terms of amine structure (aromatic, linear primary aliphatic, α-branched primary aliphatic, secondary aliphatic and diamines). Workup consisted of a simple washing with water and purification could be achieved by crystallization, avoiding the use of organic solvents in extraction and chromatographic purification steps. This protocol provides a solution to the long-standing synthetic

  在2当量苯酚的存在下，用胺对9-氯ac啶，4-氯喹啉和4-氯喹唑啉等分子混合物与胺进行聚焦微波辐照，可以实现胺化杂环的一般，快速和高产率合成，胺结构（芳族，线性伯脂肪族，α-支化伯脂肪族，仲脂肪族和二胺）。后处理包括简单的水洗和结晶纯化，避免在萃取和色谱纯化步骤中使用有机溶剂。该协议为解决长期合成问题提供了解决方案，该问题实现了一种实用有效的方法来胺化π不足的氮杂环以用于药物化学应用。
• 一种N-取代喹啉-4-胺类化合物及其制备、药物组合物和应用
  申请人：西安市第五医院

  公开号：CN115160296A

  公开（公告）日：2022-10-11

  本发明涉及药物化学和药物治疗学领域，具体涉及作为乙酰胆碱酯酶抑制剂的通式I的一类N‑取代喹啉‑4‑胺类化合物，可用于治疗阿尔兹海默症和预防有机磷毒剂中毒的解毒药物。本发明还涉及该类化合物的制备方法、这类化合物以及其在药物学上可接受的盐、异构体、溶剂化物、前药和药物组合物。
• Activity of piperaquine and other 4-aminoquinoline antiplasmodial drugs against chloroquine-sensitive and resistant blood-stages of Plasmodium falciparum
  作者：David C. Warhurst、John C. Craig、Ipemida S. Adagu、R. Kiplin Guy、Peter B. Madrid、Quinton L. Fivelman

  DOI：10.1016/j.bcp.2007.03.011

  日期：2007.6

  Chloroquine (CQ), a 4-aminoquinoline, accumulates in acidic digestive vacuoles of the malaria parasite, preventing conversion of toxic haematin to beta-haematin. We examine how bis 4-aminoquinoline piperaquine (PQ) and its hydroxy-modification (OH-PQ) retain potency on chloroquine-resistant (CQ-R) Plasmodium falciparum. For CO, PQ, OH-PQand 4 and 5, representing halves of PQ P-haematin inhibitory activity (BHIA) was assayed, while potency was determined in CQ-sensitive (CQ-S) and CQ-R P. falciparum. From measured pK(a)s and the pH-modulated distribution of base between water and lipid (log D), the vacuolar accumulation ratio (VAR) of charged drug from plasma water (pH 7.4) into vacuolar water (pH 4.8) and lipid accumulation ratio (LAR) were calculated. All agents were active in BHIA. In CQ-S, PQ, OH-PQ and CQ were equally potent while 4 and 5 were 100 times less potent. CQ with two basic centres has a VAR of 143,482, while 4 and 5, with two basic centres of lower pK(a)s have VARs of 1287 and 1966. In contrast PQ and OH-PQ have four basic centres and achieve VARs of 104,378 and 19,874. This confirms the importance of VAR for potency against CQ-S parasites. Contrasting results were seen in CQ-R. 5, PQ and OH-PQ with LARs of 693; 973,492 and 398,118 (compared with 8.25 for CQ) showed similar potency in CQ-S and CQ-R. Importance of LAR for potency against CQ-R parasites probably reflects ability to block efflux by hydrophobic interaction with PfCRT but may relate to P-haematin inhibition in vacuolar lipid. (c) 2007 Elsevier Inc. All rights reserved.
• Proline derivatives and use thereof as drugs
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP1930319B1

  公开（公告）日：2012-05-02