(alphaE)-alpha-[(3,4-二羟基-5-硝基苯基)亚甲基]-beta-氧代-1-哌啶丙腈 | 1150310-15-8

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: (alphaE)-alpha-[(3,4-二羟基-5-硝基苯基)亚甲基]-beta-氧代-1-哌啶丙腈
• 中文别名: (ALPHAE)-ALPHA-[(3,4-二羟基-5-硝基苯基)亚甲基]-BETA-氧代-1-哌啶丙腈
• 英文名称: (E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(piperidine-1-carbonyl)acrylonitrile
• 英文别名: (2E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(piperidin-yl-1-carbonyl)prop-2-ennitrile；(2E)-3-(3,4-Dihydroxy-5-nitrophenyl)-2-(piperidin-1-ylcarbonyl)prop-2-ennitrile；(E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(piperidine-1-carbonyl)prop-2-enenitrile
• CAS: 1150310-15-8
• 化学式: C₁₅H₁₅N₃O₅
• 分子量: 317.301
• InChiKey: NVHDZUJODMCISU-IZZDOVSWSA-N

物化性质

• 熔点：
  207-208℃ (ethanol )

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4-二羟基-5-硝基苯甲醛 在 哌啶 、 氯化亚砜 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (alphaE)-alpha-[(3,4-二羟基-5-硝基苯基)亚甲基]-beta-氧代-1-哌啶丙腈
  参考文献：
  名称：

  Efficient Approach to Pure Entacapone and Related Compounds

  摘要：

  A new and efficient process through a new intermediate, (2E)-2-cyano-3(3,4-dihydroxy-5-nirtrophenyl)prop-2-enoic acid 15, has been described for preparing substantially pure entacapone 1. This new intermediate 15 was prepared by Knoevenagel condensation of 3,4-dihydroxy-5-nitrobenzaldehyde 2 with 2-cyanoacetic acid 14 and was further condensed with diethylamine to get pure entacapone 1. Some of the important process-related impurities of entacapone (17, 18, 19, and 20) were also prepared easily from this intermediate 15.

  DOI：

  10.1080/00397911.2010.539894

文献信息

• [EN] FTO INHIBITORS<br/>[FR] INHIBITEURS DE FTO
  申请人：NAT INST OF BIOLOGICAL SCIENCES BEIJING

  公开号：WO2016206573A1

  公开（公告）日：2016-12-29

  The invention provides compounds that inhibit FTO (fat mass and obesity), including pharmaceutically acceptable salts, hydrides and stereoisomers thereof. The compounds are employed in pharmaceutical compositions, and methods of making and use, including treating a person in need thereof, particularly obesity, with an effective amount of the compound or composition, and detecting a resultant improvement in the person's health or condition.

  这项发明提供了抑制FTO（脂肪质量和肥胖）的化合物，包括药用可接受的盐、氢化物和立体异构体。这些化合物用于制备药物组合物，以及制备和使用的方法，包括使用有效量的化合物或组合物治疗有需要的人，特别是肥胖症，并检测人的健康或状况的改善。
• The synthesis and biological evaluation of some caffeic acid amide derivatives: E-2-Cyano-(3-substituted phenyl)acrylamides
  作者：Wei Zhou、Hai-bo Li、Chun-nian Xia、Xian-ming Zheng、Wei-xiao Hu

  DOI：10.1016/j.bmcl.2009.02.081

  日期：2009.4

  A series of caffeic acid amide derivatives 2-cyano-(3-substituted phenyl)acrylamides were synthesized via Knoevenogal condensation of substituted benzaldehydes with cyanoacetamides. The structure of compound 1f was determined as E-isomer by X-ray diffractive analysis. The biological screening tests in vitro showed that compound 1b has obvious inhibitory activities against human gastric carcinoma cell

  通过取代苯甲醛与氰基乙酰胺的Knoevenogal缩合反应，合成了一系列咖啡酸酰胺衍生物2-氰基-（3-取代的苯基）丙烯酰胺。通过X射线衍射分析确定化合物1f的结构为E-异构体。体外生物筛选试验表明，化合物1b对人胃癌细胞系BGC-823，人鼻咽癌细胞系KB和人肝癌细胞系BEL-7402具有明显的抑制活性，IC 50值为5.6μg/ mL，13.1μg。 / mL和12.5μg/ mL。还提出了一些初步的构效关系（SAR），这可能为进一步研究提供指导。
• FTO inhibitors
  申请人：National Institute of Biological Sciences, Beijing

  公开号：US10988440B2

  公开（公告）日：2021-04-27

  The invention provides compounds that inhibit FTO (fat mass and obesity), including pharmaceutically acceptable salts, hydrides and stereoisomers thereof. The compounds are employed in pharmaceutical compositions, and methods of making and use, including treating a person in need thereof, particularly obesity, with an effective amount of the compound or composition, and detecting a resultant improvement in the person's health or condition.

  本发明提供了抑制 FTO（脂肪量和肥胖）的化合物，包括其药学上可接受的盐、氢化物和立体异构体。这些化合物用于药物组合物中，其制造和使用方法包括用有效量的化合物或组合物治疗有需要的人，特别是肥胖症患者，并检测患者健康或病情的改善情况。
• FTO INHIBITORS
  申请人：National Institute Of Biological Sciences, Beijing

  公开号：EP3303283B1

  公开（公告）日：2021-04-21
• FTO Inhibitors
  申请人：National Institute of Biological Sciences, Beijing

  公开号：US20180118665A1

  公开（公告）日：2018-05-03

  The invention provides compounds that inhibit FTO (fat mass and obesity), including pharmaceutically acceptable salts, hydrides and stereoisomers thereof. The compounds are employed in pharmaceutical compositions, and methods of making and use, including treating a person in need thereof, particularly obesity, with an effective amount of the compound or composition, and detecting a resultant improvement in the person's health or condition.