N-(7-chloro-[4]quinolyl)-N'-isopropyl-propanediyldiamine | 5418-54-2

• 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'-isopropyl-propanediyldiamine
• 英文别名: N-(7-Chlor-[4]chinolyl)-N'-isopropyl-propandiyldiamin；n-(7-Chloroquinolin-4-yl)-n'-(propan-2-yl)propane-1,3-diamine；N-(7-chloroquinolin-4-yl)-N'-propan-2-ylpropane-1,3-diamine
• CAS: 5418-54-2
• 化学式: C₁₅H₂₀ClN₃
• 分子量: 277.797
• InChiKey: XSEQDLPSDCETSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  6
• 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：

  聚合甲醛 、 N-(7-chloro-[4]quinolyl)-N'-isopropyl-propanediyldiamine 、 对乙酰氨基酚 以 乙醇 、 水 为溶剂， 反应 79.0h， 以18.5%的产率得到N-[3-[[3-[(7-chloroquinolin-4-yl)amino]propyl-propan-2-ylamino]methyl]-4-hydroxyphenyl]acetamide
  参考文献：
  名称：

  Antimalarial Dual Drugs Based on Potent Inhibitors of Glutathione Reductase from Plasmodium falciparum

  摘要：

  Plasmodium parasites are exposed to higher fluxes of reactive oxygen species and need high activities of intracellular antioxidant systems providing a steady glutathione flux. As a future generation of dual drugs, 18 naphthoquinones and phenols (or their reduced forms) containing three different linkers between the 4-aminoquinoline core and the redox active component were synthesized. Their antimalarial effects have been characterized in parasite assays using chloroquine-sensitive and -resistant strains of Plasmodium, alone or in drug combination, and in the Plasmodium berghei rodent model. In particular, two tertiary amides 34 and 36 showed potent antimalarial activity in the low nanomolar range against CQ-resistant parasites. The ability to compete both for (Fe-III)protoporphyrin and for chloroquine transporter was determined. The data are consistent with the presence of a carrier for uptake of the short chloroquine analogue 2 but not for the potent antimalarial amide 34, suggesting a mode of action distinct from chloroquine mechanism.

  DOI：

  10.1021/jm7009292
• 作为产物：
  描述：

  3-(异丙基氨基)丙腈 在 镍 作用下， 100.0 ℃ 、11.77 MPa 条件下， 生成 N-(7-chloro-[4]quinolyl)-N'-isopropyl-propanediyldiamine
  参考文献：
  名称：

  Pearson; Jones; Cope, Journal of the American Chemical Society, 1946, vol. 68, p. 1227

  摘要：

  DOI：

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
• TRIOXANE DIMERS HAVING HIGH ANTICANCER AND LONG-LASTING ANTIMALARIAL ACTIVITIES
  申请人：Posner Gary H.

  公开号：US20090291923A1

  公开（公告）日：2009-11-26

  The invention provides novel trioxane dimers having formulae III, IV or V: methods for their preparation, pharmaceutical compositions containing these compounds, and methods for treating cancer and/or malaria using these compounds and compositions.
• [EN] TRIOXANE DIMERS HAVING HIGH ANTICANCER AND LONG-LASTING ANTIMALARIAL ACTIVITIES<br/>[FR] DIMERES DE TRIOXANE PRESENTANT UNE FORTE ACTIVITE ANTICANCEREUSE ET UNE LONGUE ACTIVITE ANTIMALARIQUE
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2007067333A2

  公开（公告）日：2007-06-14

  [EN] The invention provides novel trioxane dimers having formulae III, IV or V: methods for their preparation, pharmaceutical compositions containing these compounds, and methods for treating cancer and/or malaria using these compounds and compositions.
  [FR] L'invention concerne de nouveaux dimères de trioxane représentés par les formules (III), (IV) ou (V), des procédés de fabrication de ces composés, des compositions pharmaceutiques contenant ces composés, et des procédés de traitement du cancer et/ou de la malaria faisant intervenir ces composés et compositions.
• Antimalarial Dual Drugs Based on Potent Inhibitors of Glutathione Reductase from <i>Plasmodium falciparum</i>
  作者：Wolfgang Friebolin、Beate Jannack、Nicole Wenzel、Julien Furrer、Thomas Oeser、Cecilia P. Sanchez、Michael Lanzer、Vanessa Yardley、Katja Becker、Elisabeth Davioud-Charvet

  DOI：10.1021/jm7009292

  日期：2008.3.13

  Plasmodium parasites are exposed to higher fluxes of reactive oxygen species and need high activities of intracellular antioxidant systems providing a steady glutathione flux. As a future generation of dual drugs, 18 naphthoquinones and phenols (or their reduced forms) containing three different linkers between the 4-aminoquinoline core and the redox active component were synthesized. Their antimalarial effects have been characterized in parasite assays using chloroquine-sensitive and -resistant strains of Plasmodium, alone or in drug combination, and in the Plasmodium berghei rodent model. In particular, two tertiary amides 34 and 36 showed potent antimalarial activity in the low nanomolar range against CQ-resistant parasites. The ability to compete both for (Fe-III)protoporphyrin and for chloroquine transporter was determined. The data are consistent with the presence of a carrier for uptake of the short chloroquine analogue 2 but not for the potent antimalarial amide 34, suggesting a mode of action distinct from chloroquine mechanism.
• Pearson; Jones; Cope, Journal of the American Chemical Society, 1946, vol. 68, p. 1227
  作者：Pearson、Jones、Cope

  DOI：——

  日期：——