trans hydroxy-L-proline N,N-dimethyl amide | 114357-98-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans hydroxy-L-proline N,N-dimethyl amide
• 英文别名: Hyp-NMe2；(2S,4R)-2-dimethylaminocarbonyl-4-hydroxypyrrolidine；(2S,4R)-4-hydroxy-N,N-dimethylpyrrolidine-2-carboxamide
• CAS: 114357-98-1
• 化学式: C₇H₁₄N₂O₂
• 分子量: 158.2
• InChiKey: ZOHZTBXVKULCNB-RITPCOANSA-N

物化性质

• 沸点：
  326.2±42.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans hydroxy-L-proline N,N-dimethyl amide 在 聚合甲醛 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 生成 (4R)-4-羟基-N,N,1-三甲基-L-脯氨酰胺
  参考文献：
  名称：

  Beta-lactam compounds

  摘要：

  一种β-内酰胺化合物，化学式为：##STR1##或其药学上可接受的盐，可用作抗微生物剂或合成抗微生物剂的中间体。

  公开号：

  US05093328A1
• 作为产物：
  描述：

  (2S,4R)-1-benzyloxycarbonyl-2-dimethylaminocarbonyl-4-hydroxypyrrolidine 在 palladium-carbon 作用下， 以 乙醇 、 水 为溶剂， 生成 trans hydroxy-L-proline N,N-dimethyl amide
  参考文献：
  名称：

  Beta-lactam compounds

  摘要：

  一种β-内酰胺化合物，化学式为：##STR1##或其药学上可接受的盐，可用作抗微生物剂或合成抗微生物剂的中间体。

  公开号：

  US05093328A1

文献信息

• Novel, potent, selective and brain penetrant vasopressin 1b receptor antagonists
  作者：Hervé Geneste、Swati Bhowmik、Marcel M. van Gaalen、Wilfried Hornberger、Charles W. Hutchins、Astrid Netz、Thorsten Oost、Liliane Unger

  DOI：10.1016/j.bmcl.2018.07.043

  日期：2018.10

  Herein we report the discovery of a novel oxindole-based series of vasopressin 1b (V1b) receptor antagonists. Introducing a substituted piperazine moiety and optimizing the southern and the northern aromatic rings resulted in potent, selective and brain penetrant V1b receptor antagonists. Compound 9c was found to be efficacious in a rat model of anti-depressant activity (3 mg/kg, ip). Interestingly

  在这里，我们报告发现一种新型的基于羟吲哚的系列加压素1b（V1b）受体拮抗剂。引入取代的哌嗪部分并优化南部和北部芳香环可产生有效，选择性和脑渗透性的V1b受体拮抗剂。发现化合物9c在抗抑郁活性的大鼠模型（3mg / kg，ip）中有效。有趣的是，尽管微粒体稳定性欠佳，但仍可实现中等的终末半衰期和中等的生物利用度。
• Beta-lactam compounds, and their production and use
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0472062A1

  公开（公告）日：1992-02-26

  A compound of the formula: which is useful as an antimicrobial agent.

  一个化学式为的化合物，可用作抗微生物剂。
• Potent and selective oxindole-based vasopressin 1b receptor antagonists with improved pharmacokinetic properties
  作者：Thorsten Oost、Gisela Backfisch、Swati Bhowmik、Marcel M. van Gaalen、Hervé Geneste、Wilfried Hornberger、Wilfried Lubisch、Astrid Netz、Liliane Unger、Wolfgang Wernet

  DOI：10.1016/j.bmcl.2011.03.012

  日期：2011.6

  Herein we report the discovery of a novel series of vasopressin 1b (V1b) receptor antagonists, starting from potent but metabolically labile oxindole SSR149415. Masking the proline N,N-dimethyl amide moiety as an oxazole and attaching a benzylic amine moiety to the northern phenyl ring resulted in potent and selective V1b receptor antagonists with improved metabolic stability and improved pharmacokinetic properties in rat. Compound 18c was found to be efficacious in a rat model of anti-depressant activity. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of [11C]SSR149415 and preliminary imaging studies using positron emission tomography
  作者：Matthias Schönberger、Carmine Leggett、Sung Won Kim、Jacob M. Hooker

  DOI：10.1016/j.bmcl.2010.03.108

  日期：2010.5

  SSR149415 was the first non-peptide vasopressin-(V-1b) receptor antagonist reported. It has been used to probe the role of V-1b receptors in animal models of depression, aggression, and stress-anxiety, and was progressed to clinical trials for the treatment of depression. Due to the interest in V-1b receptors as a therapeutic target and the growing use of SSR149415 in preclinical research, we developed a method to label SSR145419 with carbon-11 and have studied its pharmacokinetics in non-human primates using positron emission tomography. (C) 2010 Elsevier Ltd. All rights reserved.
• Beta-lactam compounds, and their production
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0243686B1

  公开（公告）日：1992-07-15