N-(7-chloro-[4]quinolyl)-N'-propyl-propanediyldiamine | 858279-61-5

• 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]quinolyl)-N'-propyl-propanediyldiamine
• 英文别名: N-(7-Chlor-[4]chinolyl)-N'-propyl-propandiyldiamin；N'-(7-chloroquinolin-4-yl)-N-propylpropane-1,3-diamine
• CAS: 858279-61-5
• 化学式: C₁₅H₂₀ClN₃
• 分子量: 277.797
• InChiKey: FVIQXFFGSDNCHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  5-氯-2-糠醛 、 N-(7-chloro-[4]quinolyl)-N'-propyl-propanediyldiamine 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 生成 N-(5-Chloro-furan-2-ylmethyl)-N'-(7-chloro-quinolin-4-yl)-N-propyl-propane-1,3-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 吡啶 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 3.0h， 生成 N-(7-chloro-[4]quinolyl)-N'-propyl-propanediyldiamine
  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

文献信息

• 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
• 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.