methyl 4-(4-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate | 292852-48-3

• 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: methyl 4-(4-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
• 英文别名: methyl 4-(4-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• CAS: 292852-48-3
• 化学式: C₂₀H₂₃NO₄
• 分子量: 341.407
• InChiKey: VTNYBNGREGVNLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对溴甲基苯甲酸 、 methyl 4-(4-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 4.25h， 以25.3%的产率得到4-((4-(3-(methoxycarbonyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinolin-4-yl)phenoxy)methyl)benzoic acid
  参考文献：
  名称：

  Discovery of 1,8-acridinedione derivatives as novel GCN5 inhibitors via high throughput screening

  摘要：

  The general control nonrepressed protein 5 (GCN5) plays a crucial role in many biological processes. Dysregulation of GCN5 has been closely related to various human diseases, especially cancers. Hence, the exploitation of small molecules targeting GCN5 is essential for drug design and academic research. Based on the amplified luminescent proximity homogeneous assay screen methodology, we performed high throughput screening and discovered a novel GCN5 inhibitor DC_G16 with 1,8-acridinedione scaffold. Structure optimization led to the identification of a highly potent inhibitor, namely DC_G16-11 with the half-maximal inhibitory concentration (IC50) value of 6.8 mu M. The binding between DC_G16-11 and GCN5 was demonstrated by NMR and SPR with a K-D of 4.2 mu M. It could also inhibit proliferation and induce cell cycle arrest and apoptosis in cancer cells while it presented minimal effects on normal cells. Herein, DC_G16-11 could be applied as a validated chemical probe for GCN5-related biological function research and presented great potential for clinical disease treatment. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.005
• 作为产物：
  描述：

  对羟基苯甲醛 、 5,5-二甲基-1,3-环己二酮 、 乙酰乙酸甲酯 在 iron(III) oxide 、 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 5.0h， 以85%的产率得到methyl 4-(4-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  Nano-ferrous ferric oxide (nano-Fe₃O₄): magnetite catalytic system for the one-pot four-component tandem imine/enamine formation-Knoevenagel–Michael-cyclocondensation reaction of dimedone, aldehydes, β-ketoesters and ammonium acetate under green media

  摘要：

  在这项工作中，磁铁矿纳米-Fe3O4被用作一种绿色、高效、异相和可重复利用的催化系统，通过在温和且无溶剂的条件下，在50°C进行芳基醛、二美酮（5,5-二甲基环己烷-1,3-二酮）、β-酮酯和乙酸铵的一锅多组分反应，进行六氢喹啉的原子经济制备。催化剂通过包括傅里叶变换红外光谱（FT-IR）、X射线衍射（XRD）、振动样品磁力计（VSM）和透射电子显微镜（TEM）等多种技术进行了合成与表征。同时，使用响应面法（中央复合设计（CCD））对反应条件的优化进行了研究。

  DOI：

  10.1039/c4ra03980g

文献信息

• Zn/MCM-41-catalyzed unsymmetrical Hantzsch reaction and the evaluation of optical properties and anti-cancer activities of the polyhydroquinoline products
  作者：Elaheh Farajzadeh Oskuie、Sajjad Azizi、Zarrin Ghasemi、Mahtab Pirouzmand、Behnaz Nikzad Kojanag、Jafar Soleymani

  DOI：10.1007/s00706-020-02549-x

  日期：2020.2

  investigated in the presence of MCM-41-supported ZnNO3. The polyhydroquinoline products which were obtained under mild conditions and very easy workup were evaluated for anti-cancer activities against MCF-7, SK-BR-3, and HT-29 of breast and colon cancer cells. The fluorescence emission of some products was also studied and their optical parameters were reported. Graphic abstract

  摘要在MCM-41负载的ZnNO 3的存在下，研究了各种芳基醛，二甲酮和3-氨基巴豆酸甲酯的三组分Hantzsch缩合反应。评价了在温和条件下和很容易处理后获得的聚氢喹啉产品对乳腺癌和结肠癌细胞的MCF-7，SK-BR-3和HT-29的抗癌活性。还研究了一些产物的荧光发射，并报道了它们的光学参数。 图形摘要
• Nano-ferrous ferric oxide (nano-Fe₃O₄): magnetite catalytic system for the one-pot four-component tandem imine/enamine formation-Knoevenagel–Michael-cyclocondensation reaction of dimedone, aldehydes, β-ketoesters and ammonium acetate under green media
  作者：Ardeshir Khazaei、Ahmad Reza Moosavi-Zare、Hadis Afshar-Hezarkhani、Vahid Khakyzadeh

  DOI：10.1039/c4ra03980g

  日期：——

  In this work, magnetite nano-Fe3O4 was applied as a green, efficient, heterogeneous and reusable catalytic system for the atomic economic preparation of hexahydroquinolines via the one-pot multi-component reaction of aryl aldehydes, dimedone (5,5-dimethylcyclohexane-1,3-dione), β-ketoesters and ammonium acetate at 50 °C under mild and solvent-free conditions. The catalyst was synthesized and characterized by several techniques including Fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), vibrating sample magnetometry (VSM) and transmission electron microscopy (TEM). Also, optimization of the reaction conditions was investigated using the response surface method Central Composite Design (CCD)}.

  在这项工作中，磁铁矿纳米-Fe3O4被用作一种绿色、高效、异相和可重复利用的催化系统，通过在温和且无溶剂的条件下，在50°C进行芳基醛、二美酮（5,5-二甲基环己烷-1,3-二酮）、β-酮酯和乙酸铵的一锅多组分反应，进行六氢喹啉的原子经济制备。催化剂通过包括傅里叶变换红外光谱（FT-IR）、X射线衍射（XRD）、振动样品磁力计（VSM）和透射电子显微镜（TEM）等多种技术进行了合成与表征。同时，使用响应面法（中央复合设计（CCD））对反应条件的优化进行了研究。
• Novel magnetic nanoparticles with ionic liquid tags as a reusable catalyst in the synthesis of polyhydroquinolines
  作者：Meysam Yarie、Mohammad Ali Zolfigol、Yadollah Bayat、Asiye Asgari、Diego A. Alonso、Abbas Khoshnood

  DOI：10.1039/c6ra16459e

  日期：——

  electron microscopy (HRTEM), thermogravimetry (TG), derivative thermal gravimetric (DTG), differential thermal (DTA) and vibrating sample magnetometer (VSM) analyses. The nanomagnetic heterogeneous catalyst was successfully applied for the synthesis of polyhydroquinoline derivatives via a four component condensation of a good range of aryl aldehydes, dimedone, ethyl acetoacetate or methyl acetoacetate

  在这项研究中，我们介绍了Fe 3 O 4 @SiO 2 @（CH 2）3 Im} C（NO 2）3作为在温和，环保的反应条件下制备聚氢喹啉衍生物四组分的新型多相可重复使用催化剂。使用FT-IR，X射线衍射（XRD），场发射扫描电子显微镜（FESEM），能量色散光谱（EDS）元素映射分析，高分辨率透射电子显微镜对新型异质可重复使用的启动子进行了结构验证（HRTEM），热重（TG），微分热重（DTG），差热（DTA）和振动样品磁力计（VSM）分析。该纳米磁性非均相催化剂被成功地用于合成聚氢喹啉衍生物。在无溶剂条件下，由一系列芳基醛，二甲酮，乙酰乙酸乙酯或乙酰乙酸甲酯（作为β-酮酸酯）和乙酸铵（作为氮源）组成的四组分缩合反应。此外，实验证据表明，Fe 3 O 4 @SiO 2 @（CH 2）3 Im} C（NO 2）3可以作为可回收的纳米磁性和可重复使用的催化剂，而收率和反应时间没有明显下降。至少八次
• MoO₂Cl₂catalyzed efficient synthesis of functionalized 3,4-dihydropyrimidin-2(1H)-ones/thiones and polyhydroquinolines: recyclability, fluorescence and biological studies
  作者：Sravanthi Devi Guggilapu、Santosh Kumar Prajapti、Atulya Nagarsenkar、Guntuku Lalita、Ganga Modi Naidu Vegi、Bathini Nagendra Babu

  DOI：10.1039/c5nj02444g

  日期：——

  MoO₂Cl₂catalyzed Biginelli, Hantzsch reactions exploring spectroscopic and biological properties of novel compounds.

  MoO₂Cl₂催化的Biginelli，Hantzsch反应，探索新化合物的光谱和生物学特性。
• Design, characterization and application of silica-bonded imidazolium-sulfonic acid chloride as a novel, active and efficient nanostructured catalyst in the synthesis of hexahydroquinolines
  作者：Ahmad Reza Moosavi-Zare、Mohammad Ali Zolfigol、Mahmoud Zarei、Abdolkarim Zare、Javad Afsar

  DOI：10.1016/j.apcata.2015.08.004

  日期：2015.9

  A novel nanostructured catalyst namely silica-bonded imidazolium-sulfonic acid chloride (SBISAC) was prepared, and fully characterized by several techniques including Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), scanning electron microscope (SEM), transmission electron microscopy (TEM) and energy dispersive X-ray analysis (EDX). The nano-compound was applied as an efficient and heterogeneous catalyst in the synthesis of hexahydroquinolines via the one-pot multi-component condensation of arylaldehydes with dimedone (5,5-dimethylcyclohexane-1,3-dione), beta-ketoesters and ammonium acetate under mild and solvent-free conditions. (C) 2015 Elsevier B.V. All rights reserved.