2-(1,3-Benzodioxol-5-yl)-6-ethylquinoline | 1443428-32-7

• 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: 2-(1,3-Benzodioxol-5-yl)-6-ethylquinoline
• 英文别名: 2-(1,3-benzodioxol-5-yl)-6-ethylquinoline
• CAS: 1443428-32-7
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: YFFNTRZKXVNLHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(2-(benzo[d][1,3]dioxol-5-yl)-6-ethyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 生成 2-(1,3-Benzodioxol-5-yl)-6-ethylquinoline
  参考文献：
  名称：

  Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensis

  摘要：

  A series of diverse simple C2-aryl quinolines was synthesized de novo via a straightforward synthesis based on the acid-catalyzed multicomponent imino Diels-Alder reactions. Seven selected quinolines were evaluated at different stages of Leishmania braziliensis parasite. Among them, the 6-ethyl-2-phenylquinoline 5f was able to inhibit the growth of promastigotes of this parasite without affecting the mammalian cells viability and decreasing the number of intracellular L. braziliensis amastigotes on BMDM macrophages. The mechanism of action studied for the selected compound consisted in: (1) alteration of parasite bioenergetics, by disrupting mitochondrial electrochemical potential and alkalinization of acidocalcisomes, and (2) inhibition of ergosterol biosynthetic pathway in promastigote forms. These results validate the efficiency of quinoline molecules as leishmanicide compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.063

文献信息

• Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensis
  作者：Daznia Bompart、Jorge Núñez-Durán、Daniel Rodríguez、Vladimir V. Kouznetsov、Carlos M. Meléndez Gómez、Felipe Sojo、Francisco Arvelo、Gonzalo Visbal、Alvaro Alvarez、Xenón Serrano-Martín、Yael García-Marchán

  DOI：10.1016/j.bmc.2013.04.063

  日期：2013.7

  A series of diverse simple C2-aryl quinolines was synthesized de novo via a straightforward synthesis based on the acid-catalyzed multicomponent imino Diels-Alder reactions. Seven selected quinolines were evaluated at different stages of Leishmania braziliensis parasite. Among them, the 6-ethyl-2-phenylquinoline 5f was able to inhibit the growth of promastigotes of this parasite without affecting the mammalian cells viability and decreasing the number of intracellular L. braziliensis amastigotes on BMDM macrophages. The mechanism of action studied for the selected compound consisted in: (1) alteration of parasite bioenergetics, by disrupting mitochondrial electrochemical potential and alkalinization of acidocalcisomes, and (2) inhibition of ergosterol biosynthetic pathway in promastigote forms. These results validate the efficiency of quinoline molecules as leishmanicide compounds. (C) 2013 Elsevier Ltd. All rights reserved.