(5H)-2-Amino-3-hydroxy-5-phenyl-furan-4-one | 153280-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (5H)-2-Amino-3-hydroxy-5-phenyl-furan-4-one
• 英文别名: 5-amino-4-hydroxy-2-phenylfuran-3(2H)-one；5-amino-4-hydroxy-2-phenylfuran-3-one
• CAS: 153280-10-5
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: DEECGRFIVYDUJN-UHFFFAOYSA-N

物化性质

• 沸点：
  330.4±42.0 °C(Predicted)
• 密度：
  1.423±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5H)-2-Amino-3-hydroxy-5-phenyl-furan-4-one 在 Amberlite IR 120 、 硫酸 、 水 、 碘 作用下， 生成 苯丙酮酸
  参考文献：
  名称：

  Unstable 1,1,2-enetriols as (probable) intermediates in the decarboxylation of .alpha.,.beta.-diketo acids

  摘要：

  During the acid hydrolyis of (hydrated) 4-aryl-2,3-diketobutyramide 2 (aryl = phenyl, o-chlorophenyl, p-methoxyphenyl), 3-aryllactic acid (5) is formed by rapid decarboxylation of the intermediate diketo acid (3). In the decarboxylation step, a further unstable intermediate is formed. The latter manifests itself by reducing 1 mol of added iodine during the hydrolysis-decarboxylation reaction, thereby forming 3-arylpyruvic acid (6), isolated instead of 5. Thus, the oxidation of the unstable intermediate by iodine is more rapid than its ketonization. It is formulated as an 1,1,2-enetriol (4), more probable than an alpha-hydroxyketene.

  DOI：

  10.1021/jo00009a029
• 作为产物：
  描述：

  potassium cyanide 、 glyoxal sodium bisulfite 、 苯甲醛 在 sodium carbonate 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 以90%的产率得到(5H)-2-Amino-3-hydroxy-5-phenyl-furan-4-one
  参考文献：
  名称：

  基于NMR光谱和量子力学计算的咪唑和恶唑的简便结构解析

  摘要：

  1,2,3-三羰基衍生物与六亚甲基四胺和乙酸铵在乙酸中的反应为咪唑的合成提供了明确的方法，而α-卤代酮在甲酰胺中的布雷德克反应同时产生了咪唑和恶唑。本文中，我们描述了一种基于NMR光谱学和量子力学计算相结合的区分这些杂环化合物的简便方法。在NMR数据中，恶唑C-2的化学位移为。150 ppm，而在咪唑中则为约150 ppm。135 ppm，约1 J C-H。恶唑的频率为250 Hz，大约为250 Hz。咪唑为210 Hz。1 Ĵ C-H的值可以从门控去耦可以容易地获得13从1 H光谱中的H-2 13 C卫星的分离中获得C光谱，甚至更简单。此外，发现从密度泛函理论获得的NMR数据与实验数据非常吻合，并且可作为鉴定Bredereck反应产物的有价值的工具。

  DOI：

  10.1016/j.tet.2009.12.019

文献信息

• Inhibitors of beta-hydroxylase for treatment of cancer
  申请人：MIDWESTERN UNIVERSITY

  公开号：US10106532B2

  公开（公告）日：2018-10-23

  The present invention relates to compounds which modulate (e.g., inhibit) the activity of beta-hydrolase (e.g., ASPH), including novel 2-aryl-5-amino-3(2H)-furanone and 2-heteroaryl-5-amino-3(2H)-furanone compounds, pharmaceutical compositions thereof, methods for their synthesis, and methods of using these compounds to modulate the activity of ASPH in an a cell-free sample, a cell-based assay, and in a subject. Other aspects of the invention relate to use of the compounds disclosed herein to ameliorate or treat cell proliferation disorders.

  本发明涉及调节（如抑制）β-水解酶（如ASPH）活性的化合物，包括新型2-芳基-5-氨基-3(2H)-呋喃酮和2-杂芳基-5-氨基-3(2H)-呋喃酮化合物、其药物组合物、其合成方法以及使用这些化合物调节无细胞样本、基于细胞的测定和受试者体内ASPH活性的方法。本发明的其他方面涉及使用本文公开的化合物来改善或治疗细胞增殖障碍。
• Isotopically-stabilized tetronimide compounds
  申请人：Midwestern University

  公开号：US10961211B2

  公开（公告）日：2021-03-30

  Isotopically-stabilized tetronimide compounds comprising one or more deuterium atoms, derivatives, and intermediates, thereof, including methods for their synthesis, pharmaceutical compositions thereof, and methods of using these compounds to interact with target molecules in cell-free samples, cell- and tissue-based assays, animal models, and in a subject are disclosed. One aspect relates to molecules that modulate the expression or catalytic activity of aspartyl (asparaginyl) β-hydroxylase (ASPH) within or on the surface of a cell. Other aspects of the invention relate to use of the molecules disclosed herein to diagnose, ameliorate, or treat cell proliferation disorders and related diseases. Related aspects include uses of the compounds to modulate the activity of viruses, as anti-hyperlipidemia agents, and as agents to ameliorate or treat thrombosis and related cardiovascular and metabolic disorders.

  本发明公开了包含一个或多个氘原子的同位素稳定的四亚胺化合物、其衍生物和中间体，包括其合成方法、其药物组合物，以及使用这些化合物在无细胞样本、基于细胞和组织的检测、动物模型和受试者体内与靶分子相互作用的方法。一个方面涉及调节细胞内或细胞表面天冬氨酰（天冬酰胺酰）β-羟化酶（ASPH）的表达或催化活性的分子。本发明的其它方面涉及本文公开的分子用于诊断、改善或治疗细胞增殖障碍及相关疾病。相关方面包括使用本发明的化合物调节病毒的活性、作为抗高脂血症的药物、以及作为改善或治疗血栓形成及相关心血管和代谢疾病的药物。
• Schmidt, M.; Albert, K.; Brindle, R., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1993, vol. 48, # 10, p. 1372 - 1380
  作者：Schmidt, M.、Albert, K.、Brindle, R.、Maichle-Moessmer, C.、Eger, K.

  DOI：——

  日期：——
• INHIBITORS OF BETA-HYDROLASE FOR TREATMENT OF CANCER
  申请人：Rhode Island Hospital

  公开号：EP2897607A2

  公开（公告）日：2015-07-29
• Inhibitors of Beta-Hydroxylase for Treatment of Cancer
  申请人：MIDWESTERN UNIVERSITY

  公开号：US20180009798A1

  公开（公告）日：2018-01-11

  The present invention relates to compounds which modulate (e.g., inhibit) the activity of beta-hydrolase (e.g., ASPH), including novel 2-aryl-5-amino-3(2H)-furanone and 2-heteroaryl-5-amino-3(2H)-furanone compounds, pharmaceutical compositions thereof, methods for their synthesis, and methods of using these compounds to modulate the activity of ASPH in an a cell-free sample, a cell-based assay, and in a subject. Other aspects of the invention relate to use of the compounds disclosed herein to ameliorate or treat cell proliferation disorders.