4-(4-氨基丁基)氨基-7-氯喹啉 | 53186-45-1

• 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
• 中文名称: 4-(4-氨基丁基)氨基-7-氯喹啉
• 英文名称: N1-(7-chloroquinolin-4-yl)butane-1,4-diamine
• 英文别名: N-(4-aminobutyl)-7-chloroquinolin-4-amine；N-(7-chloroquinolin-4-yl)butane-1,4-diamine；N-(7-chloro-4-quinolyl)-1,4-diaminobutane；4-(4-Aminobutyl)amino-7-chloroquinoline；N'-(7-chloroquinolin-4-yl)butane-1,4-diamine
• CAS: 53186-45-1
• 化学式: C₁₃H₁₆ClN₃
• 分子量: 249.743
• InChiKey: FIVQKRXTOFYZCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  122-124 °C
• 沸点：
  438.3±40.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  4-(4-氨基丁基)氨基-7-氯喹啉 在 吡啶 、 dimethyl sulfide borane 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 20.0h， 生成 N-(7-chloroquinolin-4-yl)-N'-propyl-N'-(thiophen-2-ylmethyl)butane-1,4-diamine
  参考文献：
  名称：

  Incorporation of an Intramolecular Hydrogen-Bonding Motif in the Side Chain of 4-Aminoquinolines Enhances Activity against Drug-Resistant P. falciparum

  摘要：

  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.

  DOI：

  10.1021/jm0600951
• 作为产物：
  描述：

  4,7-二氯喹啉 在 苯酚 作用下， 生成 4-(4-氨基丁基)氨基-7-氯喹啉
  参考文献：
  名称：

  [EN] NUCLEOSIDE AND NUCLEOTIDE CONJUGATE COMPOUNDS AND USES THEREOF
  [FR] COMPOSÉS CONJUGUÉS DE NUCLÉOSIDE ET DE NUCLÉOTIDE ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2021202669A3

文献信息

• Synthesis and antimalarial activity of new 4-amino-7-chloroquinolyl amides, sulfonamides, ureas and thioureas
  作者：Kekeli Ekoue-Kovi、Kimberly Yearick、Daniel P. Iwaniuk、Jayakumar K. Natarajan、John Alumasa、Angel C. de Dios、Paul D. Roepe、Christian Wolf

  DOI：10.1016/j.bmc.2008.11.009

  日期：2009.1

  We report the synthesis and in vitro antimalarial activities of more than 50 7-chloro-4-aminoquinolyl-derived sulfonamides 3–8 and 11–26, ureas 19–22, thioureas 23–26, and amides 27–54. Many of the CQ analogues prepared for this study showed submicromolar antimalarial activity versus HB3 (chloroquine sensitive) and Dd2 (chloroquine resistant strains of Plasmodium falciparum) and low resistance indices

  我们报告了 50 多种 7-氯-4-氨基喹啉衍生的磺酰胺3 – 8和11 – 26、尿素19 – 22、硫脲23 – 26和酰胺27 – 54的合成和体外抗疟活性。许多为本研究制备的 CQ 类似物显示出亚微摩尔级抗疟活性，而 HB3（对氯喹敏感）和 Dd2（恶性疟原虫的氯喹抗性菌株）) 和低电阻指数在大多数情况下获得。侧链长度的系统变化和氟化脂肪族和芳香族末端的引入揭示了克服 CQ 抗性的有希望的线索。特别是，磺酰胺3具有短侧链和末端丹磺酰部分，结合了高抗疟原虫效力和低抗性指数，对 HB3 和 Dd2 寄生虫的IC 50 s 分别为 17.5 和 22.7 nM。
• [EN] ASYMMETRIC BISAMINOQUINOLINES AND BISAMINOQUINOLINES WITH VARIED LINKERS AS AUTOPHAGY INHIBITORS FOR CANCER AND OTHER THERAPY<br/>[FR] BISAMINOQUINOLINES ASYMÉTRIQUES ET BISAMINOQUINOLINES COMPORTANT DIVERSES SÉQUENCES DE LIAISON POUVANT ÊTRE UTILISÉES EN TANT QU'INHIBITEURS DE L'AUTOPHAGIE POUR LE TRAITEMENT DU CANCER ET D'AUTRES MALADIES
  申请人：UNIV PENNSYLVANIA

  公开号：WO2016022956A1

  公开（公告）日：2016-02-11

  The invention provides novel asymmetric and symmetric bisaminoquinolmes and related compounds, methods of treatment and syntheses. The novel compounds exhibit effective anticancer activity and are useful in the treatment of a variety of autophagy-related disorders.

  这项发明提供了新型的不对称和对称双氨基喹啉和相关化合物，治疗方法和合成方法。这些新型化合物表现出有效的抗癌活性，并可用于治疗各种与自噬相关的疾病。
• New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model
  作者：Jelena Konstantinović、Erkan Kiris、Krishna P. Kota、Johanny Kugelman-Tonos、Milica Videnović、Lisa H. Cazares、Nataša Terzić Jovanović、Tatjana Ž. Verbić、Boban Andjelković、Allen J. Duplantier、Sina Bavari、Bogdan A. Šolaja

  DOI：10.1021/acs.jmedchem.7b01710

  日期：2018.2.22

  The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative

  描述了使用基于体外HPLC的酶法测定各种甾体，苯并噻吩，噻吩和金刚烷4-氨基喹啉衍生物对A型肉毒杆菌神经毒素轻链（BoNT / A LC）的合成和抑制能力。另外，评估了化合物在小鼠胚胎干细胞衍生的运动神经元中对BoNT / A全毒素的活性。甚至在中毒后30分钟给药，类固醇衍生物16也显示出显着的保护作用（高达89％的未裂解SNAP-25）。这似乎是LC抑制剂在暴露后模型中拮抗小鼠胚胎干细胞衍生的运动神经元（mES-MNs）中BoNT中毒的第一个例子。口服16 高达600 mg / kg，qd的小鼠具有良好的耐受性，尽管在该剂量下未达到足够的未结合药物水平，但体外ADMET的良好结果有力地支持了该系列的进一步工作。
• Dual molecules containing a peroxide derivative, synthesis and therapeutic applications thereof
  申请人：——

  公开号：US20040038957A1

  公开（公告）日：2004-02-26

  The invention relates to dual molecules formed from coupling products complying with the formula 1 wherein A represents a residue of molecule with anti-malarial activity, Y 1 and Y 2 , represent a linear or ramified alkylene chain at C1 to C5, with the possibility of either Y 1 or Y 2 being absent, U is an amine, amide, sulphonamide, carboxyl, ether or thioether function, said function linking Y 1 and Y 2 , Z 1 and Z 2 , represent a linear arylene or alkylene, with the possibility of either Z 1 or Z 2 being absent, or Z 1 +Z 2 together represent a polycyclic structure including the junction carbons Ci and Cj, R 1 and R 2 , represent a hydrogen atom or a functional group capable of increasing the hydrosolubility of the dual molecule, R x and R y form a cyclic peroxide with 4 to 8 chain links, Cj being one of the peaks of said cyclic peroxide, or R x or R y is a cyclic peroxide with 4 to 8 chain links, which may comprise 1 or 2 additional oxygen atoms in the cyclic structure, and one or more substituents R 3 , identical or different, at least one representing a halogen atom, an —OH group, a —CF 3 group, an aryl, an alkyl or alkoxy at C1 to C5, —NO 2 , the other substituent(s) having one of these correspondences or a hydrogen, and their addition salts with pharmacological acceptable acids. Application as medicinal products with anti-malarial activity.

  本发明涉及由符合公式1的偶联产物形成的双分子 1 其中 A代表具有抗疟疾活性的分子的残基， Y 1 和Y 2 代表C1至C5的直链或支链亚烷基，Y 1 或Y 2 可能不存在， U是胺、酰胺、磺酰胺、羧酸、醚或硫醚官能团，所述官能团连接Y 1 和Y 2 ， Z 1 和Z 2 代表直链芳基或亚烷基，Z 1 或Z 2 可能不存在，或者Z 1 和Z 2 共同代表包括连接碳Ci和Cj的多环结构， R 1 和R 2 代表氢原子或能增加双分子水溶性的功能团， R x 和R y 形成具有4至8个链环的环状过氧化物，Cj是该环状过氧化物的一个峰，或者 R x 或R y 是具有4至8个链环的环状过氧化物，其中环状结构中可能包含1或2个额外的氧原子，以及一个或多个R 3 取代基，相同或不同，至少一个代表卤素原子、—OH基团、—CF 3 基团、芳基、C1至C5的烷基或烷氧基、—NO 2 ，其他取代基具有这些对应关系中的一个或氢， 以及它们与药理学上可接受酸的加成盐。 用作具有抗疟疾活性的药物的应用。
• COMPOSITIONS AND METHODS FOR ENHANCING CELLULAR UPTAKE AND INTRACELLULAR DELIVERY OF LIPID PARTICLES
  申请人：Lin Paulo J.C.

  公开号：US20120264810A1

  公开（公告）日：2012-10-18

  Compositions, methods and compounds useful for enhancing the uptake of a lipid particle b\ a cell are described In particular embodiments, the methods of the invention include contacting a cell with a lipid particle and a compound that binds a Na+/K+ ATPase to enhance uptake of the lipid particle b\ the cell Related compositions useful in practicing methods include lipid particles comprising a conjugated compound that enhances uptake of the lipid particles b\ the cell The methods and compositions are useful in delivering a therapeutic agent to a cell, e g for the treatment of a disease or disorder in a subject

  描述了用于增强细胞对脂质粒的摄取的组成物、方法和化合物。在特定的实施例中，发明的方法包括将细胞与脂质粒和一种与Na+/K+ ATPase结合的化合物接触，以增强细胞对脂质粒的摄取。在实践方法中使用的相关组成物包括包含一种共轭化合物的脂质粒，该共轭化合物增强细胞对脂质粒的摄取。这些方法和组成物可用于将治疗剂递送到细胞中，例如用于治疗主体中的疾病或失调。