6,8-dibromo-2-(4-methoxyphenyl)-2,3-dihydroquinolin-4(1H)-one | 1171953-49-3

• 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: 6,8-dibromo-2-(4-methoxyphenyl)-2,3-dihydroquinolin-4(1H)-one
• 英文别名: 6,8-dibromo-2-(4-methoxyphenyl)-2,3-dihydro-1H-quinolin-4-one
• CAS: 1171953-49-3
• 化学式: C₁₆H₁₃Br₂NO₂
• 分子量: 411.093
• InChiKey: BRDITIXGXDAPAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,8-dibromo-2-(4-methoxyphenyl)-2,3-dihydroquinolin-4(1H)-one 在 bis-triphenylphosphine-palladium(II) chloride 、 碘 、 potassium carbonate 、 thallium(III) p-tosylate 、 三环己基膦 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 水 为溶剂， 反应 21.0h， 生成 4-methoxy-2-(4-methoxyphenyl)-6,8-diphenylquinoline
  参考文献：
  名称：

  Suzuki–Miyaura cross-coupling of 2-aryl-6,8-dibromo-1,2,3,4-tetrahydroquinolin-4-ones and subsequent dehydrogenation and oxidative aromatization of the resulting 2,6,8-triaryl-1,2,3,4-tetrahydroquinolin-4-ones

  摘要：

  Dichlorobis(triphenylphosphine)palladium(II)/tricyclohexylphosphine-catalyzed Suzuki-Miyaura cross-coupling of the 2-aryl-6,8-dibromo-1,2,3,4-tetrahydroquinolin-4-ones with arylboronic acids afforded the corresponding 2,6,8-triaryl-1,2,3,4-tetrahydroquinolin-4-ones, exclusively. The latter was subjected to thallium(III) p-tolylsulfonate (TTS) in dimethoxyethane under reflux or to molecular iodine in methanol at reflux to afford the 2,6,8-triarylquinolin-4-(1H)-ones and 2,6,8-triaryl-4-methoxyquinoline derivatives, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.085
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 磷酸 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 6,8-dibromo-2-(4-methoxyphenyl)-2,3-dihydroquinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines

  摘要：

  碘-甲醇介导的2-芳基-6,8-二溴-2,3-二氢喹啉-4(1H)-酮的氧化芳构化以高浓度提供相应的2-芳基-6,8-二溴-4-甲氧基-喹啉。产量和纯度。异构体 1-(2-氨基-3,5-二溴苯基)-3-芳基-2-丙烯-1-酮在甲醇中与碘反应，在单锅操作中得到相应的 2-芳基-6,8-二溴- 4-甲氧基喹啉（主要）和2-芳基-6,8-二溴喹啉-4(1H)-酮（次要）产物，通过硅胶柱色谱依次分离。 6,8-二溴-4-甲氧基喹啉衍生物与过量芳基乙烯基硼酸的铃木-宫浦交叉偶联得到相应的2-芳基-6,8-双(2-芳基乙烯基)-4-甲氧基喹啉。还测定了这些化合物的吸收和荧光特性。

  DOI：

  10.3390/molecules171214186

文献信息

• Reactivity of the 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1$H)$-ones in a palladium catalyzed Sonogashira cross-coupling reaction
  作者：Malose Jack MPHAHLELE、Felix Adetunji OYEYIOLA

  DOI：10.3906/kim-1505-42

  日期：——

  Pd/C-PPh$_3}$--CuI catalyzed Sonogashira cross-coupling of the 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1$H)$-ones with phenyl acetylene or 3-butyn-1-ol afforded the corresponding 8-alkynylated quinolin-4(1$H)$-one derivatives, exclusively. Double carbo-substitution to afford the 6,8-dialkynyl derivatives was observed when PdCl$_2}$(PPh$_3})_2}$ was used as Pd(0) source. The monoalkynylated derivatives were, in turn, subjected to PdCl$_2}$ in acetonitrile under reflux to afford either the corresponding 2,4-diaryl-8-bromopyrrolo[3,2,1-\textitij}]quinolinones or the 8-(4-hydroxybutanoyl)-substituted quinolinone derivatives, exclusively. Suzuki--Miyaura cross-coupling of the 2-aryl-6-bromo-8-(alkynyl)quinolin-4-ones afforded the 2,4,8-trisubstituted pyrrolo[3,2,1-\textitij}]quinolin-6-ones.

  在Pd/C-PPh$_3}$--CuI催化的Sonogashira偶联反应中，2-芳基-6,8-二溴-2,3-二氢喹啉-4(1$H)$-酮与苯乙炔或3-丁炔-1-醇反应，专一性地得到相应的8-炔基喹啉-4(1$H)$-酮衍生物。当使用PdCl$_2}$(PPh$_3})_2}$作为Pd(0)源时，观察到双碳取代得到6,8-二炔基衍生物。单炔基化衍生物在回流条件下使用PdCl$_2}$在乙腈中进行反应，专一性地得到相应的2,4-二芳基-8-溴吡咯并[3,2,1-ij]喹啉酮或8-(4-羟基丁酰基)取代的喹啉酮衍生物。Suzuki--Miyaura偶联反应中，2-芳基-6-溴-8-(炔基)喹啉-4-酮得到2,4,8-三取代的吡咯并[3,2,1-ij]喹啉-6-酮。
• One-Pot Site-Selective Sonogashira Cross-Coupling–Heteroannulation of the 2-Aryl-6,8-Dibromoquinolin-4(1<i>H</i>)-Ones: Synthesis of Novel 6-<i>H</i>-Pyrrolo[3,2,1-<i>ij</i>]Quinolin-6-Ones
  作者：Malose J. Mphahlele、Felix A. Oyeyiola

  DOI：10.3184/174751914x14097554893763

  日期：2014.9

  The 2-aryl-6,8-dibromoquinolin-4(1 H)-ones were subjected to site-selective Sonogashira cross-coupling with terminal acetylenes as models for C sp²-C sp bond formation in the presence of Pd/C–PPh₃ and CuI as catalysts and K₂CO₃ as a base in dioxane to afford the 2-substituted 4-aryl-8-bromo-4 H-pyrrolo[3,2,1- ij]quinolin-6-ones. These were, in turn, subjected to Suzuki–Miyaura cross-coupling with 4-fluorophenylboronic acid as coupling partner to afford the 2-substituted 4,8-diaryl-4 H-pyrrolo[3,2,1- ij]quinolin-6-ones.

  2- 芳基-6,8-二溴喹啉-4(1 H)-酮在二噁烷中，以 Pd/C-PPh3 和 CuI 为催化剂，以 K2CO3 为碱的存在下，与作为 C sp2-C sp 键形成模型的末端乙炔进行位点选择性 Sonogashira 交叉偶联，得到 2-取代的 4- 芳基-8-溴-4 H-吡咯并[3,2,1-ij]喹啉-6-酮。然后，以 4-氟苯硼酸为偶联剂，对这些化合物进行 Suzuki-Miyaura 交叉偶联，得到 2-取代的 4,8-二芳基-4H-吡咯并[3,2,1-ij]喹啉-6-酮。
• NOVEL TETRAHYDROQUINOLINES AS AROMATASE INHIBITORS
  申请人：AKKINEPALLY Raghuram Rao

  公开号：US20100280070A1

  公开（公告）日：2010-11-04

  The invention relates to synthesis and biological screening of novel tetrahydroquinolines of formula (I), their derivatives, their stereoisomers, their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them for aromatase inhibition: (I). The present invention also relates to a process for the preparation of the novel tetrahydroquinolines, their derivatives, their stereoisomers, their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them. These compounds are useful in for aromatase inhibition, particularly in the treatment and/or prevention of cancer, particularly breast cancer, more particularly hormone dependent breast cancer.

  本发明涉及公式（I）的新型四氢喹啉的合成和生物筛选，其衍生物，其立体异构体，其药学上可接受的盐和含有它们的药学上可接受的组合物，用于芳香酶抑制：（I）。本发明还涉及一种制备新型四氢喹啉，其衍生物，其立体异构体，其药学上可接受的盐和含有它们的药学上可接受的组合物的方法。这些化合物在芳香酶抑制中有用，特别是在治疗和/或预防癌症，特别是乳腺癌，更特别是激素依赖性乳腺癌方面。
• [EN] NOVEL TETRAHYDROQUINOLINES AS AROMATASE INHIBITORS<br/>[FR] NOUVELLES TÉTRAHYDROQUINOLÉINES EN TANT QU'INHIBITEURS D'AROMATASE
  申请人：PANJAB UNIVERSITY

  公开号：WO2009087684A3

  公开（公告）日：2010-11-04
• Synthesis, evaluation of 6,8-dibromo-2-aryl-2,3-dihydroquinolin-4(1H)-ones in MCF-7 (breast cancer) cell lines and their docking studies
  作者：Lakshmi Narayana Bheemanapalli、Amandeep Kaur、Ramandish Arora、Sangeeta、Raghuram Rao Akkinepally、Narashima Murthy Javali

  DOI：10.1007/s00044-011-9688-z

  日期：2012.8

  A series of novel 6,8-dibromo-2-aryl-2,3-dihydroquinolin-4(1H)-ones have been synthesized and evaluated in vitro (in MCF-7 breast cancer cell lines). Compounds 5a, 5d, 5e, and 5g exhibited potent GI(50) and TGI values compared with reference standard and compounds 5b and 5c showed moderate activity. The docking studies (in silico) were conducted to recognize the hypothetical binding motif of the title compounds within the active site of aromatase enzyme employing GOLD docking software. The binding mode and SAR of the title compounds has been proposed based on the docking studies.