3-chloro-1-(2-hydroxy-4,5-dimethoxyphenyl)-propan-1-one | 352210-85-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-chloro-1-(2-hydroxy-4,5-dimethoxyphenyl)-propan-1-one
• 英文别名: 3-chloro-1-(2-hydroxy-4,5-dimethoxyphenyl)propan-1-one；6-(3-chloropropanoyl)-3,4-dimethoxyphenol
• CAS: 352210-85-6
• 化学式: C₁₁H₁₃ClO₄
• 分子量: 244.675
• InChiKey: WGXLUCGUTVUSBW-UHFFFAOYSA-N

物化性质

• 沸点：
  398.4±42.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-1-(2-hydroxy-4,5-dimethoxyphenyl)-propan-1-one 在 pyridinium hydrobromide perbromide 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 氯仿 为溶剂， 反应 68.67h， 生成 1-(7,8-dimethoxy-4H-chromeno[4,3-d]thiazol-2-yl)hydrazine
  参考文献：
  名称：

  Synthesis of Rigidified eIF4E/eIF4G Inhibitor-1 (4EGI-1) Mimetic and Their in Vitro Characterization as Inhibitors of Protein–Protein Interaction

  摘要：

  The 4EGI-1 is the prototypic inhibitor of eIF4E/eIF4G interaction, a potent inhibitor of translation initiation in vitro and in vivo and an efficacious anticancer agent in animal models of human cancers. We report on the design, synthesis, and in vitro characterization of a series of rigidified mimetic of this prototypic inhibitor in which the phenyl in the 2-(4-(3,4-dichlorophenyl)thiazol-2-yl) moiety was bridged into a tricyclic system. The bridge consisted one of the following: ethylene, methylene oxide, methylenesulfide, methylenesulfoxide, and methylenesulfone. Numerous analogues in this series were found to be markedly more potent than the parent prototypic inhibitor in the inhibition of eIF4E/eIF4G interaction, thus preventing the eIF4F complex formation, a rate limiting step in the translation initiation cascade in eukaryotes, and in inhibition of human cancer cell proliferation.

  DOI：

  10.1021/jm401733v
• 作为产物：
  描述：

  3,4-二甲氧基苯酚 、 3-氯丙酰氯 在 三氟化硼乙醚 作用下， 反应 5.0h， 生成 3-chloro-1-(2-hydroxy-4,5-dimethoxyphenyl)-propan-1-one
  参考文献：
  名称：

  对抗阿尔茨海默氏病的多靶点药物设计策略：异黄酮类曼尼希碱衍生物可作为乙酰胆碱酯酶和单胺氧化酶B双重抑制剂，具有多种功能

  摘要：

  设计，合成和评估了一系列高异黄酮类曼尼希碱衍生物，作为对抗阿尔茨海默氏病的多功能药物。结果表明，大多数衍生物是具有良好多功能性能的选择性AChE和MAO-B双重抑制剂。其中，化合物10D显示的综合优势，具有优良的胆碱酯酶和MAO-B的抑制活性（IC 50  = 2.49±0.08 nM的和1.74±0.0581μM，分别地），良好的自我和Cu 2+诱导的阿β 1-42聚集抑制能力，抗氧化活性，生物金属螯合能力和高BBB渗透性。这些多功能特性使10d 作为开发有效的抗AD药物的优秀候选者。

  DOI：

  10.1016/j.bmc.2016.11.048

文献信息

• [EN] PYRAZOLE COMPOUNDS AS MODULATORS OF FSHR AND USES THEREOF<br/>[FR] COMPOSÉS DE PYRAZOLE À TITRE DE MODULATEURS DE FSHR ET LEURS UTILISATIONS
  申请人：MERCK PATENT GMBH

  公开号：WO2014209980A1

  公开（公告）日：2014-12-31

  The present invention relates to pyrazole compounds, and pharmaceutically acceptable compositions thereof, useful as positive allosteric modulators of follicle stimulating hormone receptor (FSHR).

  本发明涉及吡唑化合物及其药用可接受的组合物，用作促卵泡生成素受体（FSHR）的阳性别构调节剂。
• Synthesis and Absolute Configuration of (−)-Neuchromenin, a Neurotrophic Metabolite ofEupenicillium javanicum var.meloforme, and Its Enantiomer
  作者：Yoshihisa Tanada、Kenji Mori

  DOI：10.1002/1099-0690(200105)2001:10<1963::aid-ejoc1963>3.0.co;2-k

  日期：2001.5

  Both the enantiomers of neuchromenin 1 (2,3-dihydro-8,9-dihydroxy-2-methyl-4H,5H-pyrano[3,2-c][1]benzopyran-4-one) were synthesized starting from the enantiomers of ethyl 3-hydoxybutanoate (7). The naturally occurring (−)-neuchromenin, a neurotrophic metabolite of Eupenicillium javanicum var. meloforme, was shown to be (S)-1.

  神经色素素 1 的两种对映体（2,3-dihydro-8,9-dihydroxy-2-methyl-4H,5H-pyrano[3,2-c][1]benzopyran-4-one）都是从对映体开始合成的3-羟基丁酸乙酯 (7)。天然存在的 (-)-neuchromenin，Eupenicillium javanicum var. 的神经营养代谢物。meloforme，显示为 (S)-1。
• PYRAZOLE COMPOUNDS AS MODULATORS OF FSHR AND USES THEREOF
  申请人：YU Henry

  公开号：US20160152626A1

  公开（公告）日：2016-06-02

  The present invention relates to pyrazole compounds, and pharmaceutically acceptable compositions thereof, useful as positive allosteric modulators of follicle stimulating hormone receptor (FSHR).

  本发明涉及吡唑化合物及其药学上可接受的组合物，作为卵泡刺激素受体（FSHR）的正向变构调节剂。
• Pyrazole compounds as modulators of FSHR and uses thereof
  申请人：MERCK PATENT GMBH

  公开号：US10081637B2

  公开（公告）日：2018-09-25

  The present invention relates to pyrazole compounds, and pharmaceutically acceptable compositions thereof, useful as positive allosteric modulators of follicle stimulating hormone receptor (FSHR).

  本发明涉及吡唑化合物及其药学上可接受的组合物，可用作促卵泡激素受体（FSHR）的正异构调节剂。
• Synthesis of Rigidified eIF4E/eIF4G Inhibitor-1 (4EGI-1) Mimetic and Their in Vitro Characterization as Inhibitors of Protein–Protein Interaction
  作者：Poornachandran Mahalingam、Khuloud Takrouri、Ting Chen、Rupam Sahoo、Evangelos Papadopoulos、Limo Chen、Gerhard Wagner、Bertal H. Aktas、Jose A. Halperin、Michael Chorev

  DOI：10.1021/jm401733v

  日期：2014.6.26

  The 4EGI-1 is the prototypic inhibitor of eIF4E/eIF4G interaction, a potent inhibitor of translation initiation in vitro and in vivo and an efficacious anticancer agent in animal models of human cancers. We report on the design, synthesis, and in vitro characterization of a series of rigidified mimetic of this prototypic inhibitor in which the phenyl in the 2-(4-(3,4-dichlorophenyl)thiazol-2-yl) moiety was bridged into a tricyclic system. The bridge consisted one of the following: ethylene, methylene oxide, methylenesulfide, methylenesulfoxide, and methylenesulfone. Numerous analogues in this series were found to be markedly more potent than the parent prototypic inhibitor in the inhibition of eIF4E/eIF4G interaction, thus preventing the eIF4F complex formation, a rate limiting step in the translation initiation cascade in eukaryotes, and in inhibition of human cancer cell proliferation.