2-(4-methoxyphenyl)-7,8-dihydroquinolin-5(6H)-one | 59838-66-3

• 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: 2-(4-methoxyphenyl)-7,8-dihydroquinolin-5(6H)-one
• 英文别名: 2-(4-methoxyphenyl)-7,8-dihydro-6H-quinolin-5-one
• CAS: 59838-66-3
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: ONRIYMNONIBKPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-7,8-dihydroquinolin-5(6H)-one 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 7'-(4-chlorophenyl)-2''-(4-methoxyphenyl)-7',7a',7'',8''-tetrahydro-1'H,3'H,5''H-dispiro[indoline-3,5'-pyrrolo[1,2-c]thiazole-6',6''-quinoline]-2,5''-dione
  参考文献：
  名称：

  Synthesis of spiro-linked quinolinone-pyrrolidine/pyrrolo[1,2-c]thiazole-oxindole/acenaphthalene hybrids via multi-component [3 + 2] cycloaddition

  摘要：

  The syntheses of novel spiro-linked quinolinone-pyrrolidine/pyrrolo[1,2-c]thiazole-oxindole/acenaphthalene hybrid heterocycles have been achieved through a one-pot three-component [3 + 2] cycloaddition strategy. The reaction proceeded stereoselectively affording these structurally intriguing multi-spiro compounds in excellent yields. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.10.002
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 cerium(III) chloride heptahydrate 、 ammonium acetate 、 sodium iodide 作用下， 以 N,N-二甲基乙酰胺 、 异丙醇 、 甲苯 为溶剂， 反应 11.0h， 生成 2-(4-methoxyphenyl)-7,8-dihydroquinolin-5(6H)-one
  参考文献：
  名称：

  Pd-catalyzed site selective C–H acetoxylation of aryl/heteroaryl/thiophenyl tethered dihydroquinolinones

  摘要：

  本文描述了一种高效的选择性氧化C–H活化/乙酰氧基化协议，适用于一系列连接有2-芳基/杂芳基/噻吩基的二氢喹啉酮，使用醋酸钯作为催化剂，碘苯二乙酸作为氧化剂。所有这些反应在立体障碍较小且电子性质良好的C–H键上进行良好，生成相应的邻位乙酰氧基化衍生物，收率良好。此外，嵌入噻吩基的二氢喹啉酮的乙酰氧基化反应导致产生单一的区域异构体，乙酰氧基在噻吩基部分的C-2位上。然而，当噻吩单元的C-2位被阻塞时，乙酰氧基则会独占性地安装在C-4位上。此外，我们注意到，二氢喹啉-5(6H)-酮-肟的乙酰氧基化并未改变配体的优先性，仍然生成邻位乙酰氧基化产物。

  DOI：

  10.1039/c3ra41312h

文献信息

• Tetrahydroquinolinones and their use as antagonists of metabotropic glutamate receptors
  申请人：Jirgensons Aigars

  公开号：US20050197361A1

  公开（公告）日：2005-09-08

  The invention relates to tetrahydroquinolinone derivatives as well as their pharmaceutially acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are group I mGluR antagonists and are therefore useful for the control and prevention of acute and/or chronic neurological disorders.

  该发明涉及四氢喹诺酮衍生物及其药用可接受的盐。该发明还涉及一种制备这种化合物的方法。该发明的化合物是I组mGluR拮抗剂，因此对于控制和预防急性和/或慢性神经系统疾病非常有用。
• Novel 5,6,7,8-tetrahydro-5-quinolines and their use as anti-inflammatory
  申请人：Schering, A.G.

  公开号：US04117135A1

  公开（公告）日：1978-09-26

  Pyridine derivatives of the formula ##STR1## wherein R.sub.1 is an alkyl, aliphatic, a cycloalkyl, or a substituted or unsubstituted hydrocarbon aryl and the substituent is halogen, alkoxy or methylenedioxy; R.sub.2 is H or Cl; X is CN, 5-tetrazolyl, or COOH or a carboxylic acid derivative; Y is H, OH, OCOR.sub.7, NH.sub.2, NHCOR.sub.8, R.sub.9, COOH or COOR.sub.10 and R.sub.7, R.sub.8, R.sub.9 and R.sub.10 are alkyl groups of 1-10 carbon atoms; A is methylene or a carbon-to-carbon bond; and R.sub.3 and R.sub.4 are each H or alkyl groups of 1-4 carbon atoms, are useful as anti-inflammatory agents.

  Pyridine衍生物的化学式为##STR1##其中R.sub.1是烷基、脂肪烷基、环烷基或取代或未取代的碳氢基芳基，取代基是卤素、烷氧基或亚甲二氧基；R.sub.2是H或Cl；X是CN、5-四唑基或COOH或羧酸衍生物；Y是H、OH、OCOR.sub.7、NH.sub.2、NHCOR.sub.8、R.sub.9、COOH或COOR.sub.10，而R.sub.7、R.sub.8、R.sub.9和R.sub.10是1-10碳原子的烷基基团；A是亚甲基或碳-碳键；而R.sub.3和R.sub.4分别是H或1-4碳原子的烷基基团，可用作抗炎药物。
• An unorthodox metal-free synthesis of dihydro-6<i>H</i>-quinoline-5-ones in ethanol/water using a non-nucleophilic base and their cytotoxic studies on human cancer cell line
  作者：Arijit Kundu、Bhaswati Bhattacharyya、Kaliprasanna Dhara、Subhabrata Paul、Indira Majumder、Rita Kundu

  DOI：10.1039/c9nj06346c

  日期：——

  DBU-catalysed metal-free domino reaction strategy has been developed for the facile synthesis of dihydro-6H-quinoline-5-ones. This protocol employs a very expedient route to the synthesis of pyridine frameworks using β-chloro-α,β-unsaturated aldehydes, 1,3-diketones, and ammonium acetate in ethanol : water (1 : 1) solvent under eco-friendly conditions. Diverse types of acyclic and cyclic β-chloro-α,β-unsaturated

  已经开发了一种DBU催化的无金属多米诺反应策略，可轻松合成二氢-6 H-喹啉-5-酮。该方案采用非常方便的途径，在生态友好的条件下，在乙醇：水（1：1）的溶剂中，使用β-氯-α，β-不饱和醛，1，3-二酮和乙酸铵合成吡啶骨架。使用多种类型的无环和环状β-氯-α，β-不饱和醛来获得各种二氢-6 H-喹啉-5-酮。通过分离中间体化合物来建立多米诺反应的机理，将其进行下一步反应以获得目标产物。中间体的结构由光谱和单晶XRD研究确定。大部分合成的二氢-6发现H-喹啉-5-酮衍生物对HeLa细胞系具有细胞毒性，在MTT分析中显示出深远的细胞毒性。DNA片段化验结果表明，处理组中没有片段化的DNA，这表明该化合物不会诱导HeLa细胞凋亡。在大多数情况下，尽管在某些情况下也观察到坏死，但从荧光显微镜研究中可明显看到自噬细胞死亡。
• Chemoselective Condensation of 3-Amino-2-cyclohexenones with Cinnamaldehydes: Switchable Synthesis of Dihydroquinolinones and Hexahydroacridinediones
  作者：Ling Jiang、Kun He、Weikun Zeng、Zhi Qiao、Xizhong Song、Kaixiu Luo、Jingbo Chen、Jun Lin、Yi Jin

  DOI：10.1021/acs.joc.3c00011

  日期：2023.5.5

  cinnamaldehydes for switchable synthesis of dihydroquinolinones and hexahydroacridinediones was developed. Mechanism analysis showed that the formation of dihydroquinolinones involved trimolecular condensation and oxidative aromatization, while the formation of hexahydroacridinediones involved acid hydrolysis of enaminone and dehydration-aromatization. This strategy provides a convenient way to switch from the

  在此，开发了 3-氨基-2-环己烯酮和肉桂醛的化学选择性缩合，用于二氢喹啉酮和六氢吖啶二酮的可切换合成。机理分析表明，二氢喹啉酮的形成涉及三分子缩合和氧化芳构化，而六氢吖啶二酮的形成涉及烯胺酮的酸水解和脱水-芳构化。该策略提供了一种从相同底物转换为生产两种不同喹啉酮衍生物的便捷方法。
• Synthesis, in vitro, and in vivo (Zebra fish) antitubercular activity of 7,8-dihydroquinolin-5(6H)-ylidenehydrazinecarbothioamides
  作者：Sandeep kumar Marvadi、Vagolu Siva Krishna、Goverdhan Surineni、Rudraraju Srilakshmi Reshma、Balasubramanian Sridhar、Dharmarajan Sriram、Srinivas Kantevari

  DOI：10.1016/j.bioorg.2020.103626

  日期：2020.3

  We, herein, describe the synthesis of a series of novel aryl tethered 7,8-dihydroquinolin-5(6H)-ylidenehydrazinecarbothioamides 4a-v, which showed in vitro and in vivo antimycobacterial activity against Mycobacterium tuberculosis (Mtb) H37Rv. The intermediates dihydro-6H-quinolin-5-ones 3a-v were synthesized from beta-enaminones, reacting with cyclochexane-1,3-dione/5,5-dimethylcyclohexane-1,3-dione and ammonium acetate using a modified Bohlmann-Rahtz reaction conditions. They were further reacted with thiosemicarbazide to give the respective hydrazine carbothioamides 4a-v. All the new analogues 4a-v, were characterized by their NMR and mass spectral data analysis. Among the twenty-two compounds screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (ATCC27294), two compounds, 4e and 4j, exhibited the highest inhibition with an MIC of 0.39 mu g/mL. Compounds 4a, 4g, and 4k were found to inhibit Mtb at an MIC of 0.78 mu g/mL. Hydrazinecarbothioamides 4a-k, exhibited enhanced activity than dihydroquinolinones 3a-k. The observed increase in potency provides a clear evidence that hydrazinecarbothioamide is a potential pharmacophore, collectively imparting synergistic effect in enhancing antitubercular activity of the dihydroquinolinone core. The in vivo (Zebra fish) antimycobacterial screening of the in vitro active molecules led to the identification of a hit compound, 4j, with significant activity in the Mtb nutrient starvation model (2.2-fold reduction). Docking studies of 4j showed a hydrogen bond with the P156 residue of the protein.