2-(3',4'-methylenedioxyphenyl)-6-methyl-quinoline | 1075185-77-1

• 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-(3',4'-methylenedioxyphenyl)-6-methyl-quinoline
• 英文别名: 2-(1,3-Benzodioxol-5-yl)-6-methylquinoline
• CAS: 1075185-77-1
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: XCTBBDDLXQEPOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  C₂₁H₂₂N₂O₃ 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 生成 2-(3',4'-methylenedioxyphenyl)-6-methyl-quinoline
  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

• A Domino Heck Coupling–Cyclization–Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines
  作者：Santanu Ghora、Chinnabattigalla Sreenivasulu、Gedu Satyanarayana

  DOI：10.1055/a-1589-7548

  日期：2022.1

  An efficient, one-pot, domino synthesis of quinolines via the coupling of iodoanilines with allylic alcohols facilitated by palladium catalysis is described. The overall synthetic process involves an intermolecular Heck coupling between 2-iodoanilines and allylic alcohols, intramolecular condensation of in situ generated ketones with an internal amine functional group, and a dehydrogenation sequence

  描述了通过钯催化促进的碘苯胺与烯丙醇的偶联来高效、单锅、多米诺合成喹啉。整个合成过程包括 2-碘苯胺和烯丙醇之间的分子间 Heck 偶联，原位生成的酮与内部胺官能团的分子内缩合，以及脱氢序列。值得注意的是，该协议以绿色溶剂的形式出现在水中。值得注意的是，该方法具有广泛的底物范围，可用于通过氘交换过程合成氘化喹啉。
• In vitro antifungal activity of polyfunctionalized 2-(hetero)arylquinolines prepared through imino Diels–Alder reactions
  作者：Carlos M. Meléndez Gómez、Vladimir V. Kouznetsov、Maximiliano A. Sortino、Sandra L. Álvarez、Susana A. Zacchino

  DOI：10.1016/j.bmc.2008.07.079

  日期：2008.9

  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.
• 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.