2-(benzo[d][1,3]dioxol-5-yl)-6-methoxyquinoline | 1075185-78-2

• 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: 2-(benzo[d][1,3]dioxol-5-yl)-6-methoxyquinoline
• 英文别名: 2-(1,3-Benzodioxol-5-yl)-6-methoxyquinoline
• CAS: 1075185-78-2
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: VDYQPGFCLJNJTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

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

  In vitro antifungal activity of polyfunctionalized 2-(hetero)arylquinolines prepared through imino Diels–Alder reactions

  摘要：

  Diverse polyfunctionalized quinolines, easily prepared using Lewis acid-catalyzed imino Diels-Alder reactions between corresponding aldimines, were tested for antifungal properties against standardized as well as clinical isolates of clinically important fungi. Among them, 4-pyridyl derivatives displayed the best activities mainly against dermatophytes. The activity appears not to be related neither to the lipophilicity nor to the basicity of compounds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.079

文献信息

• Facile synthesis of substituted quinolines by iron(<scp>iii</scp>)-catalyzed cascade reaction between anilines, aldehydes and nitroalkanes
  作者：Sachinta Mahato、Anindita Mukherjee、Sougata Santra、Grigory V. Zyryanov、Adinath Majee

  DOI：10.1039/c9ob01294j

  日期：——

  A library of substituted quinolines has been synthesized by the reaction of aldehydes, anilines and nitroalkanes using a catalytic amount of Fe(iii) chloride. The reaction is a simple, efficient, one-pot, three-component domino strategy in ambient air which afforded the products in high yields. A probable pathway of the reaction is a sequential aza-Henry reaction/cyclization/denitration. The use of

  通过醛，苯胺和硝基烷烃的催化反应，使用催化量的三价氯化铁（Fe（iii））合成了取代的喹啉文库。该反应是在环境空气中的一种简单，有效，一锅，三组分的多米诺骨牌策略，从而以高收率提供了产物。反应的可能途径是顺序的氮杂-亨利反应/环化/脱硝。使用可商购的化学品作为起始原料，廉价的金属催化剂，好氧反应条件，宽泛的官能团耐受性和操作简便性是本方案的显着优点。
• Copper-Catalyzed Decarboxylative Cascade Cyclization for the Synthesis of 2-Arylquinolines
  作者：Rana Chatterjee、Mohanreddy Pothireddy、Rambabu Dandela

  DOI：10.1055/a-1990-3283

  日期：——

  efficient copper-catalyzed intermolecular decarboxylative cascade cyclization has been developed that uses readily accessible starting materials and less-expensive reagents. A one-pot reaction of an aryl aldehyde, an aniline, and acrylic acid permits the direct synthesis of 2-substituted quinolines through the sequential formation of C–N and C–C bonds. Furthermore, the three-component, one-pot, domino

  已经开发出一种有效的铜催化分子间脱羧级联环化，它使用容易获得的起始材料和较便宜的试剂。芳基醛、苯胺和丙烯酸的一锅反应允许通过依次形成 C-N 和 C-C 键直接合成 2-取代的喹啉。此外，三组分、一锅、多米诺骨牌策略具有良好的化学和区域选择性，并且还可以耐受多种底物，具有出色的官能团耐受性、高产率、自由基反应途径和好氧反应条件。
• 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.