(S,Z)-tert-butyl 4-(3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate | 1431611-01-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S,Z)-tert-butyl 4-(3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: tert-butyl (4S)-4-[(Z)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1431611-01-6
• 化学式: C₁₅H₂₅NO₅
• 分子量: 299.367
• InChiKey: UCMRQUXRYUIJBZ-IEHMKBBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S,Z)-tert-butyl 4-(3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 在 盐酸 、 4-二甲氨基吡啶 、 potassium permanganate 、 palladium diacetate 、 对甲苯磺酸 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 32.17h， 生成 (1S,2R)-2-((S)-amino(carboxy)methyl)-1-ethylcyclopropanecarboxylic acid hydrochloride
  参考文献：
  名称：

  Development of 2′-Substituted (2S,1′R,2′S)-2-(Carboxycyclopropyl)glycine Analogues as Potent N-Methyl-d-aspartic Acid Receptor Agonists

  摘要：

  A series of 2'-substituted analogues of the selective NMDA receptor ligand (2S,1'R,2'S)-2-(carboxycyclopropyl)glycine ((S)-CCG-IV) have been designed, synthesized, and pharmacologically characterized. The design was based on a docking study hypothesizing that substituents in the 2'-position would protrude into a region where differences among the NMDA receptor GluN2 subunits exist. Various synthetic routes were explored, and two different routes provided a series of alkyl-substituted analogues. Pharmacological characterization revealed that these compounds are NMDA receptor agonists and that potency decreases with increasing size of the alkyl groups. Variations in agonist activity are observed at the different recombinant NMDA receptor subtypes. This study demonstrates that it is possible to introduce substituents in the 2'-position of (S)-CCG-IV while maintaining agonist activity and that variation among NMDA receptor subtypes may be achieved by probing this region of the receptor.

  DOI：

  10.1021/jm400346a
• 作为产物：
  描述：

  (R)-(+)-3-Boc-2,2-二甲基恶唑啉-4-甲醛 、 bis(2,2,2-trifluoroethyl) 1-(methoxycarbonyl)ethylphosphonate 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以89%的产率得到(S,Z)-tert-butyl 4-(3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Development of 2′-Substituted (2S,1′R,2′S)-2-(Carboxycyclopropyl)glycine Analogues as Potent N-Methyl-d-aspartic Acid Receptor Agonists

  摘要：

  A series of 2'-substituted analogues of the selective NMDA receptor ligand (2S,1'R,2'S)-2-(carboxycyclopropyl)glycine ((S)-CCG-IV) have been designed, synthesized, and pharmacologically characterized. The design was based on a docking study hypothesizing that substituents in the 2'-position would protrude into a region where differences among the NMDA receptor GluN2 subunits exist. Various synthetic routes were explored, and two different routes provided a series of alkyl-substituted analogues. Pharmacological characterization revealed that these compounds are NMDA receptor agonists and that potency decreases with increasing size of the alkyl groups. Variations in agonist activity are observed at the different recombinant NMDA receptor subtypes. This study demonstrates that it is possible to introduce substituents in the 2'-position of (S)-CCG-IV while maintaining agonist activity and that variation among NMDA receptor subtypes may be achieved by probing this region of the receptor.

  DOI：

  10.1021/jm400346a

文献信息

• ANTIVIRAL AZASUGAR-CONTAINING NUCLEOSIDES
  申请人：BioCryst Pharmaceuticals, Inc.

  公开号：US20170267681A1

  公开（公告）日：2017-09-21

  Disclosed are compounds comprising an azasugar attached to a heterocyclic base, including pharmaceutically acceptable salts thereof, suitable for use in inhibiting viral RNA polymerase activity or viral replication, and treating viral infections. The compounds are characterized, in part, by favorable pharmacokinetics for the active pharmaceutical ingredient, particularly in conjunction with enteral administration, including, in particular, oral administration. Also disclosed are pharmaceutical compositions comprising one or more compounds mentioned above, or pharmaceutically acceptable salts thereof, as well as methods for preparing same. Also provided are methods for inhibiting viral RNA polymerase activity, viral replication, and treating viral infections.