7-chloro-N-(piperidin-4-yl)quinolin-4-amine

• 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: 7-chloro-N-(piperidin-4-yl)quinolin-4-amine
• 英文别名: 7-chloro-N-piperidin-4-ylquinolin-4-amine
• 化学式: C₁₄H₁₆ClN₃
• mdl: MFCD11546789
• 分子量: 261.754
• InChiKey: NZOUCFSCCGQINP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.357
• 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：

  7-chloro-N-(piperidin-4-yl)quinolin-4-amine 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 tert-butyl (5-((4-(4-((7-chloroquinolin-4-yl)amino)piperidin-1-yl)butyl)(methyl)amino)pentyl)carbamate
  参考文献：
  名称：

  [EN] ACRIDIN-9-YL-AMINE, QUINOLIN-9-YL-AMINE, 1 -AMINO-9H-THIOXANTHENE-9-ONE AND BENZO[B][1,5]NAPHTHYRI DIN-10-YL-AMINE DERIVATIVES AS AUTOPHAGY INHIBITORS FOR TREATING CANCER
  [FR] DÉRIVÉS D'ACRIDIN-9-YL-AMINE, DE QUINOLIN-9-YL-AMINE, DE 1 -AMINO-9H-THIOXANTHÈNE-9-ONE ET DE BENZO[B][1,5]NAPHTYRIDIN-10-YL-AMINE UTILSÉS COMME INHIBITEURS DE L'AUTOPHAGIE POUR LE TRAITEMENT DU CANCER

  摘要：

  本公开提供了一种脱氧胸苷-9-基胺、喹啉-9-基胺、1-氨基-9H-噻吩并[1,5]苯并并[1,5]萘啉-10-基胺衍生物和结构相关化合物，用作治疗癌症的自噬抑制剂。本描述公开了示例化合物的合成和表征，以及其药理数据（例如第77页至155页；示例1至22；化合物A；化合物1至21；表1至3）。

  公开号：

  WO2021142065A1
• 作为产物：
  描述：

  4,7-二氯喹啉 在 sodium hydroxide 、 苯酚 作用下， 以 乙醇 为溶剂， 反应 384.0h， 生成 7-chloro-N-(piperidin-4-yl)quinolin-4-amine
  参考文献：
  名称：

  对恶性疟原虫疟疾具有高效力的不对称双喹啉

  摘要：

  在现代药物开发的历史中，基于喹啉的支架一直是抗疟药物的中流砥柱，包括许多青蒿素联合疗法 (ACTs)。尽管在寻找新型抗疟支架方面取得了很大进展，但喹啉可能仍然有用，特别是如果发现了此类非常有效的化合物。我们在此报告了结构-活性关系 (SAR) 研究的结果，该研究评估了潜在的不对称双喹啉抗疟原虫药物候选物，该研究使用针对细胞培养中完整寄生虫的体外活性。发现许多不对称双喹啉对氯喹敏感和对氯喹具有抗性的恶性疟原虫寄生虫均具有高度效力。

  DOI：

  10.3390/molecules25092251

文献信息

• PYRIDINE, QUINOLINE AND PYRIMIDINE DERIVATIVES
  申请人：Christ D. Andreas

  公开号：US20080064697A1

  公开（公告）日：2008-03-13

  This invention is concerned with compounds of the formula wherein A, R 1 to R 5 are as defined in the specification and G is a pyridine, quinoline or pyrimidine group as defined in the specification, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.

  这项发明涉及以下式的化合物 其中A，R1至R5如规范中所定义，G是规范中定义的吡啶，喹啉或嘧啶基团，以及其药用盐。该发明还涉及含有这种化合物的药物组合物，以及用于制备它们的过程以及它们用于治疗和/或预防与调节SST受体亚型5相关的疾病。
• Antiprotozoal Activities of Tetrazole-quinolines with Aminopiperidine Linker
  作者：Patrick Hochegger、Johanna Faist、Werner Seebacher、Robert Saf、Pascal Mäser、Marcel Kaiser、Robert Weis

  DOI：10.2174/1573406414666181015115101

  日期：2019.5.20

  highly effective makes them almost useless. Therefore new drugs against both diseases are urgently needed. OBJECTIVE Recently, we reported the synthesis and antiprotozoal activities of a number of new 2- substituted 4-carbamoyl- and 4-aminoquinolines. This study focussed on the synthesis of novel tetrazole derivatives which are linked to the quinoline core via a piperidine ring. METHODS Novel compounds

  背景技术人类非洲锥虫病（HAT，昏睡病）和疟疾都是昆虫介导的热带疾病。仅有两种药物能够治愈HAT，但所有药物均具有毒性，容易产生耐药性，需要肠胃外给药。疟疾是人类高发病率和高死亡率的原因。它是全球儿童杀手之一。对曾经有效的传统疗法的广泛耐药性使它们几乎毫无用处。因此，迫切需要针对这两种疾病的新药。目的最近，我们报道了许多新的2-取代的4-氨基甲酰基-和4-氨基喹啉的合成和抗虫活性。这项研究的重点是通过哌啶环与喹啉核心连接的新型四唑衍生物的合成。方法通过Ugi-叠氮化物反应制备具有7-氯喹啉和四唑环的新型化合物。修饰仅限于接头的方向和取代。测试了化合物对布鲁氏罗氏锥虫（STIB 900）的活性。确定了它们对恶性疟原虫的敏感性（NF54）和多抗性菌株（K1）的抗血浆活性。结果制备了十八种四唑衍生物。将生物学测试的结果与所用药物的活性进行了比较，并讨论了构效关系。他们的抗锥虫活性只有中等水平。相
• Chloroquine–astemizole hybrids with potent in vitro and in vivo antiplasmodial activity
  作者：Chitalu C. Musonda、Gavin A. Whitlock、Michael J. Witty、Reto Brun、Marcel Kaiser

  DOI：10.1016/j.bmcl.2008.11.047

  日期：2009.1

  A dual activity, conjugated approach has been taken to form hybrid molecules of two known antimalarial drugs, chloroquine (CQ) and the non-sedating H1 antagonist astemizole. A variety of linkers were investigated to conjugate the two agents into one molecule. Compounds 5-8 possessed improved in vitro activity against a CQ-resistant strain of Plasmodium falciparum, and examples 7 and 8 were active in vivo in mouse models of malaria. (C) 2008 Elsevier Ltd. All rights reserved.
• Squaric acid/4-aminoquinoline conjugates: Novel potent antiplasmodial agents
  作者：Carlos J.A. Ribeiro、S. Praveen Kumar、Jiri Gut、Lídia M. Gonçalves、Philip J. Rosenthal、Rui Moreira、Maria M.M. Santos

  DOI：10.1016/j.ejmech.2013.08.037

  日期：2013.11

  We report the synthesis and structure activity relationship (SAR) analysis of a series of hybrid compounds containing a squaric moiety conjugated with heterocyclic moieties from well-known antimalarials. This novel series of compounds presents improved antiplasmodial activity compared with the squaric derivatives described in our previous work. Three compounds, 8b (IC50 = 99 nM), 8c (IC50 = 95 nM), and 8d (IC50 = 105 nM) had greater in vitro potency than chloroquine 1 (IC50 = 140 nM) against chloroquine resistant Plasmodium falciparum. In addition, they were noncytotoxic against NIH 3T3 and Hek 293T cells. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Incorporation of an Intramolecular Hydrogen-Bonding Motif in the Side Chain of 4-Aminoquinolines Enhances Activity against Drug-Resistant <i>P. </i><i>f</i><i>alciparum</i>
  作者：Peter B. Madrid、Ally P. Liou、Joseph L. DeRisi、R. Kiplin Guy

  DOI：10.1021/jm0600951

  日期：2006.7.1

  Previous data showing that several chloroquine analogues containing an intramolecular hydrogen-bonding motif were potent against multidrug-resistant P. falciparum led to the exploration of the importance of this motif. A series of 116 compounds containing four different alkyl linkers and various aromatic substitutions with hydrogen bond accepting capability was synthesized. The series showed broad potency against the drug-resistant W2 strain of P. falciparum. In particular, a novel series containing variations of the alpha-aminocresol motif gave eight compounds with IC50 values more potent than 5 nM against the W2 strain. Such simple modifications, significantly altering the pK(a) and sterics of the basic side chain in chloroquine analogues, may prove to be part of a strategy for overcoming the problem of worldwide resistance to affordable antimalarial drugs.