N¹-(7-chloroquinolin-4-yl)-N³-cyclohexylpropane-1,3-diamine | 47218-35-9

• 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: N¹-(7-chloroquinolin-4-yl)-N³-cyclohexylpropane-1,3-diamine
• 英文别名: AM1009；N-(7-chloro-[4]quinolyl)-N'-cyclohexyl-propanediyldiamine；N-(7-Chlor-[4]chinolyl)-N'-cyclohexyl-propandiyldiamin；N'-(7-chloroquinolin-4-yl)-N-cyclohexylpropane-1,3-diamine
• CAS: 47218-35-9
• 化学式: C₁₈H₂₄ClN₃
• 分子量: 317.862
• InChiKey: BEDDWNMGYOHYNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-环己氨基丙腈 在 氨 、 镍 作用下， 120.0~155.0 ℃ 、17.16 MPa 条件下， 生成 N¹-(7-chloroquinolin-4-yl)-N³-cyclohexylpropane-1,3-diamine
  参考文献：
  名称：

  合成抗疟药；某些4-氨基喹啉的制备。

  摘要：

  DOI：

  10.1021/ja01211a021

文献信息

• A chloroquinoline derivate presents effective in vitro and in vivo antileishmanial activity against Leishmania species that cause tegumentary and visceral leishmaniasis
  作者：Jessica K.T. Sousa、Luciana M.R. Antinarelli、Débora V.C. Mendonça、Daniela P. Lage、Grasiele S.V. Tavares、Daniel S. Dias、Patrícia A.F. Ribeiro、Fernanda Ludolf、Vinicio T.S. Coelho、João A. Oliveira-da-Silva、Luísa Perin、Bianka A. Oliveira、Denis F. Alvarenga、Miguel A. Chávez-Fumagalli、Geraldo C. Brandão、Vandack Nobre、Guilherme R. Pereira、Elaine S. Coimbra、Eduardo A.F. Coelho

  DOI：10.1016/j.parint.2019.101966

  日期：2019.12

  The identification of new therapeutics to treat leishmaniasis is desirable,,since available drugs are toxic and present high cost and/or poor availability. Therefore, the discovery of safer, more effective and selective pharmaceutical options is of utmost importance. Efforts towards the development of new candidates based on molecule analogs with known biological functions have been an interesting and cost-effective strategy. In this context, quinoline derivatives have proven to be effective biological activities against distinct diseases. In the present study, a new chloroquinoline derivate, AM1009, was in vitro tested against two Leishmania species that cause leishmaniasis. The present study analyzed the necessary inhibitory concentration to preclude 50% of the Leishmania promastigotes and axenic amastigotes (EC50 value), as well as the inhibitory concentrations to preclude 50% of the murine macrophages and human red blood cells (CC50 and RBC50 values, respectively). In addition, the treatment of infected macrophages and the inhibition of infection using pre-treated parasites were also investigated, as was the mechanism of action of the molecule in L. amazonensis. To investigate the in vivo therapeutic effect, BALB/c mice were infected with L. amazonensis and later treated with AM1009. Parasitological and immunological parameters were also evaluated. Clioquinol, a known antileishmanial quinoline derivate, and amphotericin B (AmpB), were used as molecule and drug controls, respectively. Results in both in vitro and in vivo experiments showed a better and more selective action of AM1009 to kill the in vitro parasites, as well as in treating infected mice, when compared to results obtained using clioquinol or AmpB. AM1009-treated animals presented significantly lower average lesion diameter and parasite burden in the infected tissue and organs evaluated in this study, as well as a more polarized antileishmanial Th1 immune response and low renal and hepatic toxicity. This result suggests that AM1009 should be considered a possible therapeutic target to be evaluated in future studies for treatment against leishmaniasis.
• 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