N-甲基-4-羟基-5-氧代-3-吡咯啉-3-羧酸乙酯铁螯合物 | 4450-97-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 中文名称: N-甲基-4-羟基-5-氧代-3-吡咯啉-3-羧酸乙酯铁螯合物
• 中文别名: 鸟苷,8-氯-2'-脱氧-(9CI)
• 英文名称: ethyl 4-hydroxy-1-methyl-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate
• 英文别名: Ethyl N-methyl-4-hydroxy-5-oxo-3-pyrroline-3-carboxylate iron chelate；ethyl 4-hydroxy-1-methyl-5-oxo-2H-pyrrole-3-carboxylate
• CAS: 4450-97-9
• 化学式: C₈H₁₁NO₄
• 分子量: 185.18
• InChiKey: DSDSKBLQRIVSTN-UHFFFAOYSA-N

物化性质

• 沸点：
  372.0±42.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  N-甲基-4-羟基-5-氧代-3-吡咯啉-3-羧酸乙酯铁螯合物 在 一水合肼 作用下， 以 乙醇 为溶剂， 以74%的产率得到Ethyl 4-hydrazinyl-1-methyl-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Facile Reduction of β-Enamino Oxopyrrolidine Carboxylates Mediated by Heterogeneous Palladium Catalyst

  摘要：

  The synthesis of diastereoisomers via diastereoselective hydrogenation of unreactive endocyclic enamine system of ethyl 4-hydrazinyl- and 4-(2-hydroxyethylamino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylates using palladium-based catalyst was developed. The steric and electronic properties of substituents, especially of the C(2)substituent, influenced both the yield and diastereoselectivity. Despite the reaction generated three chiral centers, the reduced compounds had eithercis-transor all-transconfiguration which was successfully determined by means of 1D and 2D NMR experiments.

  DOI：

  10.1134/s1070428020060184
• 作为产物：
  描述：

  3-(甲基氨基)丙酸甲酯 、 草酸二乙酯 在 乙醇 、 sodium ethanolate 作用下， 反应 3.0h， 生成 methyl 4-hydroxy-1-methyl-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate 、 N-甲基-4-羟基-5-氧代-3-吡咯啉-3-羧酸乙酯铁螯合物
  参考文献：
  名称：

  [EN] NOVEL PYRAZOLO-PYRROLO-PYRIMIDINE-DIONE DERIVATIVES AS P2X3 INHIBITORS
  [FR] NOUVEAUX DÉRIVÉS DE PYRAZOLO-PYRROLO-PYRIMIDINE-DIONE UTILISÉS EN TANT QU'INHIBITEURS DE P2X3

  摘要：

  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。

  公开号：

  WO2019081343A1

文献信息

• 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。
• A Facile Synthesis of Pyrrolidine-Based Iminosugars as Potential Alpha-Glucosidase Inhibitors
  作者：Muhamad Zulfaqar Bacho、Mohd Fazli Mohammat、Zurina Shaameri、Agustono Wibowo、Firdaus Kamarulzaman、Ahmad Sazali Hamzah

  DOI：10.13005/ojc/360214

  日期：2020.4.28

  stereoselective reduction reactions was used to synthesize new pyrrolidine-based iminosugars. The key step of this strategy involves the contruction of a highly functionalised pyrroldine ring skeleton through MCR approach. Subsequently, amination and reduction reactions to the ring skeleton provide a quick access to new pyrrolidine-based imino sugars. The iminosugars were then tested against alpha glucosidase

  包含MCR（多组分反应），胺化反应和立体选择性还原反应的多方面方法用于合成新的吡咯烷基亚氨基糖。该策略的关键步骤涉及通过MCR方法构建高度官能化的吡咯烷环骨架。随后，对环骨架的胺化和还原反应可快速获得新的基于吡咯烷的亚氨基糖。然后测试亚氨基糖的α-葡糖苷酶活性，其中发现一种化合物（4-（（4-甲氧基苯基）氨基）吡咯烷丁-3-醇）在低剂量下最有效。
• Diastereoselective Reduction of 2,3-Dioxo-4-carboxy-5-substituted Pyrrolidines Using NaBH₄/AcOH and Heterogenous Hydrogenation Reactions
  作者：Mohd Fazli Mohammat、Nurul Shulehaf Mansor、Zurina Shaameri、Ahmad Sazali Hamzah

  DOI：10.5012/jkcs.2015.59.1.31

  日期：2015.2.20

  Diastereoselective reduction of 2,3-dioxo-4-carboxy-5-(substituted)pyrrolidine 1 by $NaBH_4/AcOH$ and heterogenous hydrogenation were reported. Stereochemical assignment and diastereomeric ratios of the products were determined using $^1H$ NMR and single crystal X-ray analyses. The steric factors of the C-5 substituents of the pyrrolidinone was shown to have an interesting influence on both the yield and diastereoselectivity of the reduced product.

  $NaBH_4/AcOH$对2,3-二氧代-4-羧基-5-(取代)吡咯烷1的非对映选择性还原和异相氢化反应已得到报道。使用$^1H$ NMR和单晶X射线分析确定了产物的立体化学分配和非对映异构体比率。吡咯烷酮C-5取代基的空间位阻因素对还原产物的产率和非对映选择性都有显著影响。
• 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。
• Sano, Takehiro; Horiguchi, Yoshie; Tsuda, Yoshisuke, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 1, p. 110 - 120
  作者：Sano, Takehiro、Horiguchi, Yoshie、Tsuda, Yoshisuke

  DOI：——

  日期：——