3-(4-methoxyphenyl)-4(1H)-quinolinone | 68305-29-3

• 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: 3-(4-methoxyphenyl)-4(1H)-quinolinone
• 英文别名: 3-(4-methoxyphenyl)quinolin-4(1H)-one；3-(4'-Methoxyphenyl)-4(1H)-quinolone；3-(4-methoxyphenyl)-1,4-dihydro-4-quinolinone；3-(4-methoxyphenyl)-1H-quinolin-4-one
• CAS: 68305-29-3
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: NOIBTXABKRMFSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  3-(4-methoxyphenyl)-4(1H)-quinolinone 在 氢溴酸 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 75.0h， 生成 1-甲基-3-(4-羟基苯基)-1H-喹啉-4-酮
  参考文献：
  名称：

  Design and synthesis of azaisoflavone analogs as phytoestrogen mimetics

  摘要：

  A series of azaisoflavone analogs were designed and synthesized and their transactivation activities and binding affinities for ER alpha and ER beta were investigated. Among these compounds, 2b and 3a were the most potent with 6.5 and 1.1 mu M of EC50, respectively. Molecular modeling study showed putative binding modes of the compound 3a in the active site of ER alpha and ER beta, which were similar with that of genistein and provided insight of the effect of N-alkyl substitution of azaisoflavones on ER beta activity. Also, a biphasic effect of azaisoflavone analogs on MCF-7 cell growth depending on their concentrations was investigated. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.030
• 作为产物：
  描述：

  4-methoxy-2′-nitrochalcone 在 三氟化硼乙醚 、 铁粉 、 溶剂黄146 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 5.08h， 生成 3-(4-methoxyphenyl)-4(1H)-quinolinone
  参考文献：
  名称：

  通过原位Meinwald重排/ 2'-硝基查耳酮环氧化物的分子内还原环化反应，可有效构建3-芳基喹啉-4（1 H）-ones

  摘要：

  通过原位Meinwald重排/分子内2'-硝基查尔酮环氧化物还原环化反应，构建3-芳基喹啉-4（1 H）-ones的一种有效方法已得到开发。实用的方法是在温和的反应条件下具有优异的官能团相容性，且产率高达98％。有关转化关键中间体的捕获和NMR分析为提出分子内还原环化的合理机理提供了见识。此外，进一步的衍生成功地提供了羟基取代的和N-甲基取代的衍生物，这可能在探索3-芳基喹啉-4（1H）-一的生物活性化合物中提供有希望的潜在应用。

  DOI：

  10.1016/j.tet.2016.09.039

文献信息

• Palladium-Catalyzed Oxidative Carbonylation for the Synthesis of Polycyclic Aromatic Hydrocarbons (PAHs)
  作者：Fanghua Ji、Xianwei Li、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/jo502013s

  日期：2014.11.21

  A direct and facile palladium-catalyzed C–H bond oxidative carbonylation reaction and oxidative cyclization for the synthesis of polycyclic aromatic hydrocarbons (PAHs) is reported herein. The intramolecular cyclocarbonylation, through C–H activation and C–C, C–O bond formations under mild conditions, proceeds smoothly with good functional group tolerance in high to excellent yields. The intramolecular

  本文报道了直接和简便的钯催化的CH键的羰基化羰基化反应和氧化环化反应，以合成多环芳烃（PAHs）。在温和的条件下，通过C–H活化和C–C，C–O键形成的分子内环羰基化可顺利进行，并具有良好的官能团耐受性，且产率高至优异。还证明了分子内钯催化的C–O键形成的直接氧化C–H键功能化，这为构建各种PAH提供了有效的方法。
• Pharmaceutical compositions comprising 4-quinolones for treating cancers
  申请人：Laboratoire L. Lafon

  公开号：US06645983B1

  公开（公告）日：2003-11-11

  A non-cytotoxic pharmaceutical composition acting on the proliferation of clonogenic cells in malignant tumors and including an efficient amount of a compound selected among the compounds of formula (I) and (Ia).

  一种非细胞毒性药物组合物，对恶性肿瘤中克隆细胞的增殖起作用，包括在式(I)和(Ia)的化合物中选择的有效量的化合物。
• Synthesis of azaisoflavones and their inhibitory activities of NO production in activated microglia
  作者：Guo Hua Jin、Sang Keun Ha、Hye Min Park、Bomi Kang、Sun Yeou Kim、Hee-Do Kim、Jae-Ha Ryu、Raok Jeon

  DOI：10.1016/j.bmcl.2008.05.106

  日期：2008.7

  A series of azaisoflavones were synthesized and their biological activities were evaluated for nitric oxide (NO) production and inducible NO synthase (iNOS) expression in BV-2 microglia cell lines. Among these compounds, compound 8d was the most potent with IC50 7.83 mu M for inhibition of NO production. Also, compound 8d inhibited expression of iNOS in LPS-induced BV2 cells. This result suggests that compound 8d inhibited the production of NO by suppressing the expression of iNOS. (c) 2008 Elsevier Ltd. All rights reserved.
• Toekes, Adrienne L.; Antus, Sandor, Liebigs Annalen der Chemie, 1993, # 8, p. 927 - 930
  作者：Toekes, Adrienne L.、Antus, Sandor

  DOI：——

  日期：——
• Construction of Azaisoflavone Derivatives by Hypervalent Iodine Reagent-Mediated Oxidative Rearrangement of 2’-Nitrochalcone
  作者：Tomohiro Maegawa、Akira Nakamura、Reo Takane、Junki Tanaka、Junya Morimoto

  DOI：10.3987/com-18-s(t)51

  日期：——

  Fabrication of a synthetic azaisoflavone skeleton from 2'-nitrochalcone was done using oxidative rearrangement with a hypervalent iodine reagent. A key intermediate compound, aminoacetal, was prepared from readily available 2'-nitrochalcone via a PhI(OH)OTs-mediated rearrangement, followed by reduction of the nitro group. A variety of azaisoflavones were obtained in moderate to high yields by treatment of the intermediate compound under acidic conditions.