ethyl 4-(2-nitrophenyl)-2,4-dioxobutanoate | 178114-28-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-(2-nitrophenyl)-2,4-dioxobutanoate
• CAS: 178114-28-8
• 化学式: C₁₂H₁₁NO₆
• mdl: MFCD07809017
• 分子量: 265.222
• InChiKey: JVOTVLRLNFEFOV-UHFFFAOYSA-N

物化性质

• 熔点：
  89-90 °C
• 沸点：
  432.3±25.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4-(2-nitrophenyl)-2,4-dioxobutanoate 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 baker's yeast 、 四丁基溴化铵 、 氢气 、 alpha-氯乙酰苯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醚 、 水 、 甲苯 为溶剂， 反应 107.0h， 生成 盐酸贝那普利
  参考文献：
  名称：

  Asymmetric synthesis of ACE inhibitor-Benazepril HCl via a bioreductive reaction

  摘要：

  An enantioselective synthesis of the potent angiotensin converting enzyme (ACE) inhibitor (2S, 3'S)-2-(1-carboxymethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl ester hydrochloride, Benazepril HCl 4, has been achieved through an asymmetric reduction of 4-(2-nitrophenyl)-2,4-dioxobutyric acid ethyl ester 6b employing baker's yeast as the reductive catalyst. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00453-1
• 作为产物：
  描述：

  邻硝基苯乙酮 、 草酸二乙酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 ethyl 4-(2-nitrophenyl)-2,4-dioxobutanoate
  参考文献：
  名称：

  [EN] AMINOPYRAZINE COMPOUNDS WITH A2A ANTAGONIST PROPERTIES
  [FR] COMPOSÉS D'AMINOPYRAZINE PRÉSENTANT DES PROPRIÉTÉS D'ANTAGONISTE A2A

  摘要：

  公开了具有公式I结构的化合物，或其任一药物可接受的盐，其中：“Z”，“R1”和“R2”按如下定义，这些化合物被认为适合用于选择性地拮抗A2a受体，例如，那些在基底神经节中密度高的受体。这种化合物和药物制剂被认为在治疗或管理神经退行性疾病方面是有用的，例如，帕金森病，或使用某些用于治疗或管理帕金森病的药物引起的运动障碍。

  公开号：

  WO2016200717A1

文献信息

• AROMATIC DERIVATIVE, PREPARATION METHOD FOR SAME, AND MEDICAL APPLICATIONS THEREOF
  申请人：Bioardis LLC

  公开号：EP3680236A1

  公开（公告）日：2020-07-15

  The present invention relates to an aromatic derivative, a preparation method thereof and medical applications thereof. Particularly, the present invention relates to a novel compound as shown in the general formula (I) and a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing the same, and a preparation method thereof. The present invention further relates to use of the derivative and a pharmaceutically acceptable salt thereof or a pharmaceutical composition containing the same, in the preparation of therapeutic agents and especially FGFR4 tyrosine kinase inhibitors, and in the preparation of a drug for treating and/or preventing diseases such as tumor and inflammation. Wherein each substituent of the general formula (I) is identical with the definition in the description.

  本发明涉及一种芳香族衍生物、其制备方法及其医学应用。特别是，本发明涉及一种通式（I）所示的新型化合物及其药学上可接受的盐、含有该化合物的药物组合物及其制备方法。本发明进一步涉及该衍生物及其药学上可接受的盐或含有该衍生物的药物组合物在制备治疗剂特别是FGFR4酪氨酸激酶抑制剂中的用途，以及在制备治疗和/或预防肿瘤和炎症等疾病的药物中的用途。其中通式（I）的各取代基与描述中的定义相同。
• Aminopyrazine compounds with A2A antagonist properties
  申请人：Merck Sharp & Dohme Corp.

  公开号：US10688082B2

  公开（公告）日：2020-06-23

  Disclosed are compounds having the structure of Formula I, or a pharmaceutically acceptable salt of any thereof, wherein: “Z”, R1 and R2 are defined herein, which compounds are believed suitable for use in selectively antagonizing the A2a receptors, for example, those found in high density in the basal ganglia. Such compounds and pharmaceutical formulations are believed to be useful in treatment or management of neurodegenerative diseases, for example, Parkinson's disease, or movement disorders arising from use of certain medications used in the treatment or management of Parkinson's disease.

  本发明公开了具有式 I 结构的化合物或其中任何一种的药学上可接受的盐，其中：Z"、R1 和 R2 在此定义，这些化合物被认为适合用于选择性拮抗 A2a 受体，例如基底神经节中高密度存在的 A2a 受体。此类化合物和药物制剂被认为可用于治疗或控制神经退行性疾病，例如帕金森病，或因使用某些用于治疗或控制帕金森病的药物而引起的运动障碍。
• Musajo et al., Gazzetta Chimica Italiana, 1950, vol. 80, p. 161,169
  作者：Musajo et al.

  DOI：——

  日期：——
• Makino et al., Kumamoto Medical Journal, 1954, vol. 6, p. 122,124
  作者：Makino et al.

  DOI：——

  日期：——
• “Untypical Aging Off-Flavor” in Wine:  Synthesis of Potential Degradation Compounds of Indole-3-acetic Acid and Kynurenine and Their Evaluation as Precursors of 2-Aminoacetophenone
  作者：Katrin Hoenicke、Ole Borchert、Kai Grüning、Thomas J. Simat

  DOI：10.1021/jf011672r

  日期：2002.7.1

  Kynurenine (1) and indole-3-acetic acid (2) are considered as potential precursors of 2-amino-acetophenone (3), which is regarded to be the aroma impact compound causing an "untypical aging off-flavor" (UTA) in Vitis vinifera wines. The mechanism of the formation of 3 was studied using model fermentation and model sulfuration media spiked with 1 or 2 as potential precursors. Possible degradation products such as kynurenamine (4) and kynurenic acid (5), or skatole (6), 2-oxoskatole (7), 2-formamidoacetophenone (8), 2-oxindole-3-acetic acid (9), and 3-(2-formylaminophenyl)-3-oxopropionic acid (10) were evaluated by HPLC-UV of the fermentation and sulfuration media and comparison with synthesized 7, 8, 9, and 10. The synthesis of the possible precursor 4-(2-aminophenyl)-2,4-dioxobutanoic acid (111), a proposed metabolite of 1 failed because a spontaneous cyclization yields 5 and N-oxo-kynurenic acid (12), but not 11. It could be shown that the formation of 3 is triggered by an oxidative degradation of 2 after sulfuration with potassium bisulfite via the intermediates 10 and 8. However, no formation of 3 occurred during sulfuration of a model wine spiked with 1 or during fermentation of a model must spiked with 1 or 2.