dimethyl (2S,3R)-N-tritylamino-β-3,5-dimethylbenzyl aspartate

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: dimethyl (2S,3R)-N-tritylamino-β-3,5-dimethylbenzyl aspartate
• 化学式: C₃₄H₃₅NO₄
• 分子量: 521.656
• InChiKey: PNUQFVDVKKULCA-JSOSNVBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	dimethyl (2S)-2-(tritylamino)butandioate	116393-72-7	C25H25NO4	403.478

反应信息

• 作为产物：
  描述：

  3,5-二甲基溴苄 、 dimethyl (2S)-2-(tritylamino)butandioate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 dimethyl (2S,3R)-N-tritylamino-β-3,5-dimethylbenzyl aspartate 、 dimethyl (2S,3S)-N-tritylamino-β-3,5-dimethylbenzyl aspartate
  参考文献：
  名称：

  Synthesis and preliminary pharmacological evaluation of novel derivatives of l-β-threo-benzylaspartate as inhibitors of the neuronal glutamate transporter EAAT3

  摘要：

  A series of beta-benzylaspartate derivatives were prepared from N-trityl-L-aspartate dimethyl ester and evaluated as inhibitors of neuronal glutamate transporter EAAT3. The result of the structure-activity studies suggests that the position occupied by the aromatic ring of beta-benzylaspartate within the binding site of EAAT3 may be different from that occupied by comparable groups in previously identified inhibitors, such as L-threo-benzyloxy aspartate (TBOA). Further, halogen substitutions at the 3-postition of the aromatic ring of beta-benzylaspartate can increase the potency with which the analogues inhibit EAAT3. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.001

文献信息

• Synthesis and preliminary pharmacological evaluation of novel derivatives of l-β-threo-benzylaspartate as inhibitors of the neuronal glutamate transporter EAAT3
  作者：Terri L. Mavencamp、Joseph F. Rhoderick、Richard J. Bridges、C. Sean Esslinger

  DOI：10.1016/j.bmc.2008.07.001

  日期：2008.8

  A series of beta-benzylaspartate derivatives were prepared from N-trityl-L-aspartate dimethyl ester and evaluated as inhibitors of neuronal glutamate transporter EAAT3. The result of the structure-activity studies suggests that the position occupied by the aromatic ring of beta-benzylaspartate within the binding site of EAAT3 may be different from that occupied by comparable groups in previously identified inhibitors, such as L-threo-benzyloxy aspartate (TBOA). Further, halogen substitutions at the 3-postition of the aromatic ring of beta-benzylaspartate can increase the potency with which the analogues inhibit EAAT3. (C) 2008 Elsevier Ltd. All rights reserved.