(S)-5-methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyloxazolidine-3-carbonyl)hexanenitrile | 850079-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-5-methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyloxazolidine-3-carbonyl)hexanenitrile
• 英文别名: 5-methyl-3S-(4R-methyl-2-oxo-5S-phenyloxazolidine-3-carbonyl)hexanenitrile；(3S)-5-methyl-3-[(4R,5S)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidine-3-carbonyl]hexanenitrile
• CAS: 850079-96-8
• 化学式: C₁₈H₂₂N₂O₃
• 分子量: 314.384
• InChiKey: BTYSGKRSFXQMGF-FVQBIDKESA-N

物化性质

• 沸点：
  506.1±50.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-5-methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyloxazolidine-3-carbonyl)hexanenitrile 在 镍 lithium hydroxide 、 ammonium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 30.0h， 生成 (s)-2-(2-Aminoethyl)-4-methylpentanoic Acid
  参考文献：
  名称：

  Structure−Activity Relationships of Pregabalin and Analogues That Target the α₂-δ Protein

  摘要：

  Pregabalin exhibits robust activity in preclinical assays indicative of potential antiepileptic, anxiolytic, and antihyperalgesic clinical efficacy. It binds with high affinity to the alpha(2)-delta subunit of voltage-gated calcium channels and is a substrate of the system L neutral amino acid transporter. A series of pregabalin analogues were prepared and evaluated for their alpha(2)-delta binding affinity as demonstrated by their ability to inhibit binding of [H-3]gabapentin to pig brain membranes and for their potency to inhibit the uptake of [H-3]leucine into CHO cells, a measure of their ability to compete with the endogenous substrate at the system L transporter. Compounds were also assessed in vivo for their ability to promote anxiolytic, analgesic, and anticonvulsant actions. These studies suggest that distinct structure activity relationships exist for alpha(2)-delta binding and system L transport inhibition. However, both interactions appear to play an important role in the in vivo profile of these compounds.

  DOI：

  10.1021/jm049762l
• 作为产物：
  描述：

  (4R,5S)-(+)-4-甲基-5-苯基-2-恶唑啉酮 在 正丁基锂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 (S)-5-methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyloxazolidine-3-carbonyl)hexanenitrile
  参考文献：
  名称：

  [EN] BETA-TETRAZOLYL-PROPIONIC ACIDS AS METALLO-BETA-LACTAMASE INHIBITORS
  [FR] ACIDES BÊTA-TÉTRAZOLYLE-PROPIONIQUES UTILES EN TANT QU'INHIBITEURS DES MÉTALLO-BÊTA-LACTAMASES

  摘要：

  本发明涉及公式I的化合物，这些化合物是金属β-内酰胺酶抑制剂，以及这些化合物的合成和与β-内酰胺类抗生素一起使用以克服抗性的用途。

  公开号：

  WO2015171474A1

文献信息

• BETA-TETRAZOLYL-PROPIONIC ACIDS AS METALLO-BETA-LACTAMASE INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP3139918A1

  公开（公告）日：2017-03-15
• US9839642B2
  申请人：——

  公开号：US9839642B2

  公开（公告）日：2017-12-12
• [EN] BETA-TETRAZOLYL-PROPIONIC ACIDS AS METALLO-BETA-LACTAMASE INHIBITORS<br/>[FR] ACIDES BÊTA-TÉTRAZOLYLE-PROPIONIQUES UTILES EN TANT QU'INHIBITEURS DES MÉTALLO-BÊTA-LACTAMASES
  申请人：MERCK SHARP & DOHME

  公开号：WO2015171474A1

  公开（公告）日：2015-11-12

  The present invention relates to compounds of formula I that are metallo-β-lactamase inhibitors, the synthesis of such compounds, and the use of such compounds for use with β-lactam antibiotics for overcoming resistance.

  本发明涉及公式I的化合物，这些化合物是金属β-内酰胺酶抑制剂，以及这些化合物的合成和与β-内酰胺类抗生素一起使用以克服抗性的用途。
• Structure−Activity Relationships of Pregabalin and Analogues That Target the α₂-δ Protein
  作者：Thomas R. Belliotti、Thomas Capiris、I. Victor Ekhato、Jack J. Kinsora、Mark J. Field、Thomas G. Heffner、Leonard T. Meltzer、Jacob B. Schwarz、Charles P. Taylor、Andrew J. Thorpe、Mark G. Vartanian、Lawrence D. Wise、Ti Zhi-Su、Mark L. Weber、David J. Wustrow

  DOI：10.1021/jm049762l

  日期：2005.4.1

  Pregabalin exhibits robust activity in preclinical assays indicative of potential antiepileptic, anxiolytic, and antihyperalgesic clinical efficacy. It binds with high affinity to the alpha(2)-delta subunit of voltage-gated calcium channels and is a substrate of the system L neutral amino acid transporter. A series of pregabalin analogues were prepared and evaluated for their alpha(2)-delta binding affinity as demonstrated by their ability to inhibit binding of [H-3]gabapentin to pig brain membranes and for their potency to inhibit the uptake of [H-3]leucine into CHO cells, a measure of their ability to compete with the endogenous substrate at the system L transporter. Compounds were also assessed in vivo for their ability to promote anxiolytic, analgesic, and anticonvulsant actions. These studies suggest that distinct structure activity relationships exist for alpha(2)-delta binding and system L transport inhibition. However, both interactions appear to play an important role in the in vivo profile of these compounds.