ethyl 4-hydroxy-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate | 57056-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: ethyl 4-hydroxy-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate
• 英文别名: ethyl 4-hydroxy-5-oxo-1-phenyl-2H-pyrrole-3- carboxylate；EBPC；Ethyl 2,5-dihydro-4-hydroxy-5-oxo-1-phenyl-1H-pyrrole-3-carboxylate；ethyl 4-hydroxy-5-oxo-1-phenyl-2H-pyrrole-3-carboxylate
• CAS: 57056-57-2
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: GQWLFHZHHVTAOT-UHFFFAOYSA-N

物化性质

• 熔点：
  132-134°C
• 沸点：
  380.5±42.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-hydroxy-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate 在 potassium cyanate 作用下， 以 水 、 溶剂黄146 为溶剂， 以82%的产率得到4-amino-5-oxo-1-phenyl-2,5-dihydro-pyrrole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Potassium Cyanate as an Amino-dehydroxylating Agent: Synthesis of Aminooxypyrrole Mono, Dicarboxylic Acid Esters, and Carbonitrile

  摘要：

  DOI：

  10.1081/scc-120021502
• 作为产物：
  描述：

  2-苯基氨基丙酸乙酯 在 sodium ethanolate 、 sodium 作用下， 以 乙醇 为溶剂， 生成 ethyl 4-hydroxy-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  N-substituted lactams useful as cholecystokinin antagonists

  摘要：

  这项发明涉及具有以下结构式的新型N-取代内酰胺，有助于治疗和预防与脊髓胆囊素（CCK）相关的哺乳动物的胃肠道、中枢神经和食欲调节系统的紊乱。

  公开号：

  US05202344A1

文献信息

• [EN] NOVEL PYRAZOLO-PYRROLO-PYRIMIDINE-DIONE DERIVATIVES AS P2X3 INHIBITORS<br/>[FR] NOUVEAUX DÉRIVÉS DE PYRAZOLO-PYRROLO-PYRIMIDINE-DIONE UTILISÉS EN TANT QU'INHIBITEURS DE P2X3
  申请人：BAYER AG

  公开号：WO2019081343A1

  公开（公告）日：2019-05-02

  The present invention covers substituted Pyrazolo-pyrrolo-pyrimidine-dione (PPPD) compounds of general formula (I): in which R1, R2 and R3 are as defined herein, methods of preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of neurogenic diseases, as a sole agent or in combination with other active ingredients.

  本发明涵盖了一般式(I)的取代吡唑基-吡咯基-嘧啶二酮（PPPD）化合物：其中R1、R2和R3如本文所定义，制备所述化合物的方法，包含所述化合物的药物组合物和配方，以及利用所述化合物制造用于治疗或预防疾病的药物组合物，特别是神经源性疾病，作为唯一活性成分或与其他活性成分组合使用。
• Synthesis and hypocholesterolemic activity of 6,7-dihydro-4H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidine-5,8-diones, novel inhibitors of acylCoA: cholesterol O-acyltransferase
  作者：Scott D. Larsen、Charles H. Spilman、Frank P. Bell、Dac M. Dinh、Esther Martinborough、Gracella J. Wilson

  DOI：10.1021/jm00109a028

  日期：1991.5

  A novel series of 6,7-dihydro-4H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidine-5,8-dione inhibitors of the enzyme acyl-CoA:cholesterol O-acyltransferase is described. A number of these derivatives were found to be potent modulators of serum lipoprotein levels in cholesterol-fed rats. Further evaluation of one of the most effective analogues confirmed that it was significantly blocking the absorption of cholesterol

  描述了酶-CoA：胆固醇O-酰基转移酶的一系列新的6,7-二氢-4H-吡唑并[1,5-a]吡咯并[3,4-d]嘧啶-5,8-二酮抑制剂。发现这些衍生物中的许多是胆固醇喂养的大鼠中血清脂蛋白水平的有效调节剂。对最有效的类似物之一的进一步评估证实，它明显阻止了肠道中胆固醇的吸收。
• Pyrazolo-pyrrolo-pyrimidine-dione derivatives as P2X3 inhibitors
  申请人：Bayer Aktiengesellschaft

  公开号：US11319324B2

  公开（公告）日：2022-05-03

  The present invention covers substituted. Pyrazolo-pyrrolo-pyrimidine-dione (PPPD) compounds of general formula (I): in which R1, R2 and R3 are as defined herein, methods of preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of neurogenic diseases, as a sole agent or in combination with other active ingredients.

  本发明涉及取代的。通式（I）的吡唑-吡咯-嘧啶二酮（PPPD）化合物（其中 R1、R2 和 R3 如本文所定义）、制备所述化合物的方法、包含所述化合物的药物组合物和组合物，以及使用所述化合物制造治疗或预防疾病（特别是神经源性疾病）的药物组合物，作为单独制剂或与其他活性成分组合使用。
• Aurora kinase A inhibitors: Identification, SAR exploration and molecular modeling of 6,7-dihydro-4H-pyrazolo-[1,5-a]pyrrolo[3,4-d]pyrimidine-5,8-dione scaffold
  作者：Mohane Selvaraj Coumar、Jian-Sung Wu、Jiun-Shyang Leou、Uan-Kang Tan、Chung-Yu Chang、Teng-Yuan Chang、Wen-Hsing Lin、John T.-A. Hsu、Yu-Sheng Chao、Su-Ying Wu、Hsing-Pang Hsieh

  DOI：10.1016/j.bmcl.2008.01.068

  日期：2008.3

  Tricyclic 6,7-dihydro-4H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidine-5,8-dione was identified as a novel scaffold for Aurora kinase A inhibition through virtual screening. SAR exploration coupled with molecular modeling of 8a reveals the minimum pharmacophore requirements for Aurora kinase A inhibition. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of New N‐(5‐Oxo‐2,5‐dihydro)pyrrol‐3‐yl Glycines and N‐(5‐Oxo‐2,5‐dihydro)pyrrol‐3‐yl Glycines Esters
  作者：Fabrice Jourdan、Jens T. Kaiser、David J. Lowe

  DOI：10.1080/00397910500191219

  日期：2005.9.1

  Following our efforts towards the synthesis of new potential inhibitors of Xanthine Dehydrogenase (XDH), we describe here a general method for the preparation of N-(5-oxo-2,5-dihydro)pyrrol-3-yl glycines and N-(5-oxo-2,5-dihydro)pyrrol-3-yl glycine esters from glycine ethyl ester hydrochloride and various 4-hydroxy5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid esters and carbonitriles.