6-ethyl-2-phenylquinoline | 860200-70-0

• 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: 6-ethyl-2-phenylquinoline
• 英文别名: 2-Phenyl-6-ethyl quinoline
• CAS: 860200-70-0
• 化学式: C₁₇H₁₅N
• 分子量: 233.313
• InChiKey: BMQIBXDNPUQJOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(6-Ethyl-2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one 在 sulfur 作用下， 反应 0.17h， 生成 6-ethyl-2-phenylquinoline
  参考文献：
  名称：

  Simple C-2-Substituted Quinolines and their Anticancer Activity

  摘要：

  对16种C-2取代的喹啉进行了人癌细胞系(MCF-7，H-460和SF-268)和正常细胞系(Vero和THP-1)的测试。初步结果表明，2-α呋喃基和2-γ吡啶基喹啉衍生物1，13和14对三种人癌细胞系具有活性，同时对正常细胞没有细胞毒性效应。生物活性和SAR结果与使用在线可用软件通过计算确定的不同的分子描述符进行了比较，试图展示这些喹啉衍生物可能的作用模式的关联。

  DOI：

  10.2174/157018012801319544

文献信息

• 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.
• Synthesis of Quinoline Derivatives by an Improved Döebner-von Miller Reaction Using a Recyclable Ag(I)-Exchanged Montmorillonite K10 Catalyst
  作者：Vineet Jeena、Janeeka Jayram

  DOI：10.3987/com-16-13564

  日期：——

  The Doebner-von Miller synthesis of quinolines under solvent-free conditions is described, catalyzed by recyclable Ag(I)-exchanged Montmorillonite K10. The desired products are obtained in good to excellent yields and the reaction accommodates both aromatic and aliphatic alpha,beta-unsaturated aldehydes making this process an attractive method for the synthesis of substituted quinolines. In addition, the Ag(I)-exchanged Montmorillonite K10 catalyst can be recovered and reused up to 5 times with excellent activity.
• Synthesis of quinolines by a solid acid-catalyzed microwave-assisted domino cyclization–aromatization approach
  作者：Omar De Paolis、Liliana Teixeira、Béla Török

  DOI：10.1016/j.tetlet.2009.03.208

  日期：2009.6

  A microwave-assisted solid acid-catalyzed synthesis of quinolines from anilines and cinnamaldehydes is described. Use of montmorillonite K-10 results in a one-pot process; the cyclization and oxidation steps readily take place in a domino approach. Reactions were completed in a matter of minutes and provided excellent yields. The efficient and ecofriendly catalyst and the convenience of the product isolation make this process an attractive alternative for the synthesis of these important heterocycles. (C) 2009 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.
• Simple C-2-Substituted Quinolines and their Anticancer Activity
  作者：Vladimir V. Kouznetsov、Fernando A. Rojas Ruiz、Leonor Y. Vargas Mendez、Mahabir P. Gupta

  DOI：10.2174/157018012801319544

  日期：2012.6.1

  Sixteen C-2-substituted quinolines were tested in both human cancer cell lines (MCF-7, H-460 and SF-268) and normal cell lines (Vero and THP-1). Preliminary results indicate that 2-α-furyl- and 2-γ-pyridinyl quinoline derivatives 1, 13 and 14 are active against three human cancer cell lines and, at the same time, were devoid of cytotoxic effect on normal cells. Biological activity and SAR results were compared with different molecular descriptors determined in silico using online available software, in an attempt to show a relationship with the possible mode of action of these quinoline derivatives.

  对16种C-2取代的喹啉进行了人癌细胞系(MCF-7，H-460和SF-268)和正常细胞系(Vero和THP-1)的测试。初步结果表明，2-α呋喃基和2-γ吡啶基喹啉衍生物1，13和14对三种人癌细胞系具有活性，同时对正常细胞没有细胞毒性效应。生物活性和SAR结果与使用在线可用软件通过计算确定的不同的分子描述符进行了比较，试图展示这些喹啉衍生物可能的作用模式的关联。