(2S,4'S)-2-(benzyloxycarbonylamino)-4-(4'-methoxycarbonyloxazolin-2-yl)-butyric acid methyl ester | 1054639-93-8

• 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: (2S,4'S)-2-(benzyloxycarbonylamino)-4-(4'-methoxycarbonyloxazolin-2-yl)-butyric acid methyl ester
• 英文别名: methyl (4S)-2-[(3S)-4-methoxy-4-oxo-3-(phenylmethoxycarbonylamino)butyl]-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 1054639-93-8
• 化学式: C₁₈H₂₂N₂O₇
• 分子量: 378.382
• InChiKey: LFHAYKNSCLNWBA-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,4'S)-2-(benzyloxycarbonylamino)-4-(4'-methoxycarbonyloxazolin-2-yl)-butyric acid methyl ester 在 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以43%的产率得到
  参考文献：
  名称：

  A Rational Approach to the Design of Selective Substrates and Potent Nontransportable Inhibitors of the Excitatory Amino Acid Transporter EAAC1 (EAAT3). New Glutamate and Aspartate Analogues as Potential Neuroprotective Agents

  摘要：

  Two three-dimensional receptor interaction models for EAAT substrates and nontransportable inhibitors have been developed, and new glutamate (Glu) and aspartate (Asp) analogues have been synthesized. The analogues la and 3 represent novel lead compounds for the development of EAAT substrates and nontransportable inhibitors, selective for EAATs over iGluRs, as possible neuroprotective agents useful to minimize the progression of chronic or acute neurodegenerative diseases, The role played by the protonatable amine function in the interaction with EAATs has been discussed.

  DOI：

  10.1021/jm015509z
• 作为产物：
  描述：

  Z-L-GluOMe 在 伯吉斯试剂 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (2S,4'S)-2-(benzyloxycarbonylamino)-4-(4'-methoxycarbonyloxazolin-2-yl)-butyric acid methyl ester
  参考文献：
  名称：

  A Rational Approach to the Design of Selective Substrates and Potent Nontransportable Inhibitors of the Excitatory Amino Acid Transporter EAAC1 (EAAT3). New Glutamate and Aspartate Analogues as Potential Neuroprotective Agents

  摘要：

  Two three-dimensional receptor interaction models for EAAT substrates and nontransportable inhibitors have been developed, and new glutamate (Glu) and aspartate (Asp) analogues have been synthesized. The analogues la and 3 represent novel lead compounds for the development of EAAT substrates and nontransportable inhibitors, selective for EAATs over iGluRs, as possible neuroprotective agents useful to minimize the progression of chronic or acute neurodegenerative diseases, The role played by the protonatable amine function in the interaction with EAATs has been discussed.

  DOI：

  10.1021/jm015509z

文献信息

• A Rational Approach to the Design of Selective Substrates and Potent Nontransportable Inhibitors of the Excitatory Amino Acid Transporter EAAC1 (EAAT3). New Glutamate and Aspartate Analogues as Potential Neuroprotective Agents
  作者：Giuseppe Campiani、Meri De Angelis、Silvia Armaroli、Caterina Fattorusso、Bruno Catalanotti、Anna Ramunno、Vito Nacci、Ettore Novellino、Christof Grewer、Diana Ionescu、Thomas Rauen、Roger Griffiths、Colin Sinclair、Elena Fumagalli、Tiziana Mennini

  DOI：10.1021/jm015509z

  日期：2001.8.1

  Two three-dimensional receptor interaction models for EAAT substrates and nontransportable inhibitors have been developed, and new glutamate (Glu) and aspartate (Asp) analogues have been synthesized. The analogues la and 3 represent novel lead compounds for the development of EAAT substrates and nontransportable inhibitors, selective for EAATs over iGluRs, as possible neuroprotective agents useful to minimize the progression of chronic or acute neurodegenerative diseases, The role played by the protonatable amine function in the interaction with EAATs has been discussed.