(2S,1'S,2'R,3'R,1''R)-N-[(2''-hydroxy-1''-phenyl)ethyl]-2-[3'-benzyloxymethyl-2'-(methoxycarbonyl)cyclopropyl] glycinonitrile | 653598-81-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,1'S,2'R,3'R,1''R)-N-[(2''-hydroxy-1''-phenyl)ethyl]-2-[3'-benzyloxymethyl-2'-(methoxycarbonyl)cyclopropyl] glycinonitrile
• 英文别名: methyl (1R,2S,3R)-2-[(S)-cyano-[[(1R)-2-hydroxy-1-phenylethyl]amino]methyl]-3-(phenylmethoxymethyl)cyclopropane-1-carboxylate
• CAS: 653598-81-3
• 化学式: C₂₃H₂₆N₂O₄
• 分子量: 394.47
• InChiKey: NNOFHGGKAPBFCW-BDHVOXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,1'S,2'R,3'R,1''R)-N-[(2''-hydroxy-1''-phenyl)ethyl]-2-[3'-benzyloxymethyl-2'-(methoxycarbonyl)cyclopropyl] glycinonitrile 在 lead(IV) acetate 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 18.17h， 生成 ethyl (2S,1'S,2'R,3'R)-N-(tert-butoxycarbonyl)-2-[3'-benzyloxymethyl-2'-(ethoxycarbonyl)cyclopropyl] glycinate
  参考文献：
  名称：

  (2S,1‘S,2‘R,3‘R)-2-(2‘-Carboxy-3‘-hydroxymethylcyclopropyl) Glycine Is a Highly Potent Group 2 and 3 Metabotropic Glutamate Receptor Agonist with Oral Activity

  摘要：

  The asymmetric synthesis and biological activity of (2S,1'S,2R,3R)-2-(2 -carboxy-3'-hydroxy-methylcyclopropyl) glycine ((+)-3) is described. This novel C-3' substituted carboxy cyclopropyl glycine is a highly potent group 2 and group 3 mGluR agonist that has proven to be orally active in both fear potentiated startle (animal model for anxiety) and PCP-induced motor activation (animal model for psychosis) assays in rats.

  DOI：

  10.1021/jm030967o
• 作为产物：
  描述：

  顺-4-苄氧基-2-丁烯-1-醇 在 咪唑 、 lithium hydroxide 、 四丙基高钌酸铵 、 Rh₂(4S-MPPIM)4 、 4-乙酰氨基苯磺酰叠氮 、 四丁基氟化铵 、 sodium acetate 、 双(三甲基硅烷基)氨基钾 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 14.67h， 生成 (2S,1'S,2'R,3'R,1''R)-N-[(2''-hydroxy-1''-phenyl)ethyl]-2-[3'-benzyloxymethyl-2'-(methoxycarbonyl)cyclopropyl] glycinonitrile
  参考文献：
  名称：

  (2S,1‘S,2‘R,3‘R)-2-(2‘-Carboxy-3‘-hydroxymethylcyclopropyl) Glycine Is a Highly Potent Group 2 and 3 Metabotropic Glutamate Receptor Agonist with Oral Activity

  摘要：

  The asymmetric synthesis and biological activity of (2S,1'S,2R,3R)-2-(2 -carboxy-3'-hydroxy-methylcyclopropyl) glycine ((+)-3) is described. This novel C-3' substituted carboxy cyclopropyl glycine is a highly potent group 2 and group 3 mGluR agonist that has proven to be orally active in both fear potentiated startle (animal model for anxiety) and PCP-induced motor activation (animal model for psychosis) assays in rats.

  DOI：

  10.1021/jm030967o

文献信息

• (2<i>S</i>,1‘<i>S</i>,2‘<i>R</i>,3‘<i>R</i>)-2-(2‘-Carboxy-3‘-hydroxymethylcyclopropyl) Glycine Is a Highly Potent Group 2 and 3 Metabotropic Glutamate Receptor Agonist with Oral Activity
  作者：Iván Collado、Concepción Pedregal、Ana Belén Bueno、Alicia Marcos、Rosario González、Jaime Blanco-Urgoiti、Javier Pérez-Castells、Darryle D. Schoepp、Rebecca A. Wright、Bryan G. Johnson、Ann E. Kingston、Eric D. Moher、David W. Hoard、Kelly I. Griffey、Joseph P. Tizzano

  DOI：10.1021/jm030967o

  日期：2004.1.1

  The asymmetric synthesis and biological activity of (2S,1'S,2R,3R)-2-(2 -carboxy-3'-hydroxy-methylcyclopropyl) glycine ((+)-3) is described. This novel C-3' substituted carboxy cyclopropyl glycine is a highly potent group 2 and group 3 mGluR agonist that has proven to be orally active in both fear potentiated startle (animal model for anxiety) and PCP-induced motor activation (animal model for psychosis) assays in rats.