5-(3-甲氧基苯基)环己烷-1,3-二酮 | 27462-91-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5-(3-甲氧基苯基)环己烷-1,3-二酮
• 中文别名: 5-(3-甲氧苯基)环己烷-1,3-二酮
• 英文名称: 5-(3-Methoxyphenyl)cyclohexane-1,3-dione
• CAS: 27462-91-5
• 化学式: C₁₃H₁₄O₃
• mdl: MFCD06660538
• 分子量: 218.252
• InChiKey: AQUXWSRUHWNKNU-UHFFFAOYSA-N

物化性质

• 熔点：
  127-132 °C
• 沸点：
  391.0±42.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  5-(3-甲氧基苯基)环己烷-1,3-二酮 在 1H-1,2,4-三唑 、 四丁基溴化铵 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 4.0h， 生成 5-(3-hydroxyphenyl)-2-(1-(o-tolylamino)ethylidene)cyclohexane-1,3-dione
  参考文献：
  名称：

  Novel Colchicine-Site Binders with a Cyclohexanedione Scaffold Identified through a Ligand-Based Virtual Screening Approach

  摘要：

  Vascular disrupting agents (VDAs) constitute an innovative anticancer therapy that targets the tumor endothelium, leading to tumor necrosis. Our approach for the identification of new VDAs has relied on a ligand 3-D shape similarity virtual screening (VS) approach using the ROCS program as the VS tool and as query colchicine and TN-16, which both bind the alpha,beta-tubulin dimer. One of the hits identified, using TN-16 as query, has been explored by the synthesis of its structural analogues, leading to 2-(1-((2-methoxyphenyl)amino)ethylidene)-5-phenylcyclohexane-1,3-dione (compound 16c) with an IC50 = 0.09 +/- 0.01 mu M in HMEC-1 and BAEC, being 100-fold more potent than the initial hit. Compound 16c caused cell cycle arrest in the G2/M phase and interacted with the colchicine-binding site in tubulin, as confirmed by a competition assay with N,N'-ethylenebis(iodoacetamide) and by fluorescence spectroscopy. Moreover, 16c destroyed an established endothelial tubular network at 1 mu M and inhibited the migration and invasion of human breast carcinoma cells at 0.4 mu M. In conclusion, our approach has led to a new chemotype of promising antiproliferative compounds with antimitotic and potential VDA properties.

  DOI：

  10.1021/jm401939g
• 作为产物：
  描述：

  3-甲氧基苯甲醛 在 丙二酸二乙酯 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 5-(3-甲氧基苯基)环己烷-1,3-二酮
  参考文献：
  名称：

  Novel Colchicine-Site Binders with a Cyclohexanedione Scaffold Identified through a Ligand-Based Virtual Screening Approach

  摘要：

  Vascular disrupting agents (VDAs) constitute an innovative anticancer therapy that targets the tumor endothelium, leading to tumor necrosis. Our approach for the identification of new VDAs has relied on a ligand 3-D shape similarity virtual screening (VS) approach using the ROCS program as the VS tool and as query colchicine and TN-16, which both bind the alpha,beta-tubulin dimer. One of the hits identified, using TN-16 as query, has been explored by the synthesis of its structural analogues, leading to 2-(1-((2-methoxyphenyl)amino)ethylidene)-5-phenylcyclohexane-1,3-dione (compound 16c) with an IC50 = 0.09 +/- 0.01 mu M in HMEC-1 and BAEC, being 100-fold more potent than the initial hit. Compound 16c caused cell cycle arrest in the G2/M phase and interacted with the colchicine-binding site in tubulin, as confirmed by a competition assay with N,N'-ethylenebis(iodoacetamide) and by fluorescence spectroscopy. Moreover, 16c destroyed an established endothelial tubular network at 1 mu M and inhibited the migration and invasion of human breast carcinoma cells at 0.4 mu M. In conclusion, our approach has led to a new chemotype of promising antiproliferative compounds with antimitotic and potential VDA properties.

  DOI：

  10.1021/jm401939g

文献信息

• [EN] INHIBITORS OF CYSTATHIONINE BETA SYNTHASE TO REDUCE THE NEUROTOXIC OVERPRODUCTION OF ENDOGENOUS HYDROGEN SULFIDE<br/>[FR] INHIBITEURS DE LA CYSTATHIONINE BÊTA SYNTHASE UTILISABLES EN VUE DE LA RÉDUCTION DE LA SURPRODUCTION NEUROTOXIQUE DE SULFURE D'HYDROGÈNE ENDOGÈNE
  申请人：FOND JEROME LEJEUNE

  公开号：WO2013068592A1

  公开（公告）日：2013-05-16

  The invention is directed to inhibitors of cystathionine beta synthase which, among other biochemical effects, allow reduction of the neurotoxic overproduction of endogenous hydrogen sulphide. These compounds and pharmaceutical compositions containing them are useful for the prevention and treatment of cognitive disorders such as cognitive disorders in Down syndrome. The invention also relates to methods for preventing or treating cognitive disorders including cognitive disorders in Down Syndrome.

  本发明涉及胱硫醚β合酶抑制剂，除其他生化作用外，还允许减少内源性硫化氢的神经毒性过度产生。这些化合物以及含有它们的药物组合物对于预防治疗认知障碍，如下氏综合症中的认知障碍等是有用的。本发明还涉及用于预防或治疗认知障碍的方法，包括下氏综合症中的认知障碍。
• Copper-catalyzed one-pot [3 + 2] cycloadditions of ethynyl indoloxazolidones with 1,3-cyclohexanediones
  作者：Qing-Qiang Su、Ruo-Nan Wang、Yong-Zheng Lv、Ya-Xin Fan、Shan Li、Hong-Li Huang、Ji-Yuan Du

  DOI：10.1039/d3ob00332a

  日期：——

  units in natural products and medicinal molecules, and methods for their introduction are of fundamental importance. Here we report one-pot cycloadditions of ethynyl indoloxazolidones with 1,3-cyclohexanediones enabled by copper catalysis, leading to a series of functionalized furan derivatives in good yields. This method features mild reaction conditions, high efficiency, and wide substrate scope

  稠合呋喃是天然产物和药用分子中常见的单元，引入它们的方法至关重要。在这里，我们报告了通过铜催化实现的乙炔基吲哚恶唑烷酮与 1,3-环己二酮的一锅法环加成，从而以良好的收率生成了一系列功能化的呋喃衍生物。该方法反应条件温和、效率高、底物适用范围广。
• A library synthesis of 4-hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as anti-tumor agents
  作者：Ichiro Hayakawa、Rieko Shioya、Toshinori Agatsuma、Hidehiko Furukawa、Shunji Naruto、Yuichi Sugano

  DOI：10.1016/j.bmcl.2004.06.067

  日期：2004.9

  As a result of a hit-to-lead program using a technique of solution-phase parallel synthesis, a highly potent (2,4-dimethoxyphenyl)- [6- (3 -fluorophenyl)-4-hydroxy- 3 -methylbenzofuran -2 -yl] methanone (15b) was synthesized as an optimized derivative of 4-hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester (1), which was discovered as a screening hit from small-molecule libraries and exhibited selective cytotoxicity against a tumorigenic cell line. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and Antimalarial Effects of Phenothiazine Inhibitors of a <i>Plasmodium falciparum</i> Cysteine Protease
  作者：José N. Domínguez、Simón López、Jaime Charris、Lúcido Iarruso、Gricela Lobo、Andrey Semenov、Jed E. Olson、Philip J. Rosenthal

  DOI：10.1021/jm970266p

  日期：1997.8.1

  Acridinediones have previously been shown to have potent antimalarial activity. A series of sulfur isosteres of acridinediones Slave been synthesized and evaluated for their inhibition of the Plasmodium falciparum cysteine protease falcipain and for their antimalarial activity. A number of these phenothiazines inhibited falcipain and demonstrated activity against cultured P, falciparum parasites at low micromolar concentrations. Wie propose that the compounds exerted their antimalarial effects by two mechanisms, one of which involves the inhibition of falcipain and a consequent block in parasite degradation of hemoglobin. These compounds and related phenothiazines are worthy of further study as potential antimalarial agents.
• Cyclohexane-1,3-Diones for Use in the Treatment of Amyotrophic Lateral Sclerosis
  申请人：Northwestern University

  公开号：US20140371313A1

  公开（公告）日：2014-12-18

  The present invention relates to the identification of provided cyclohexane-1,3-diones (CHD compounds) and pharmaceutical compositions thereof for treating subjects with amyotrophic lateral sclerosis (ALS) and other neurodegenerative diseases. The invention also provides methods of preparing the provided CHD compounds.