1-methyl-N-((3aR,5r,6aS)-2-methyloctahydrocyclopenta[c]pyrrol-5-yl)-N-(3-(trifluoromethoxy)benzyl)-1H-imidazole-4-carboxamide | 1031332-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-methyl-N-((3aR,5r,6aS)-2-methyloctahydrocyclopenta[c]pyrrol-5-yl)-N-(3-(trifluoromethoxy)benzyl)-1H-imidazole-4-carboxamide
• CAS: 1031332-83-8
• 化学式: C₂₁H₂₅F₃N₄O₂
• 分子量: 422.45
• InChiKey: BPFSRDSVMKDEAX-BJWYYQGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  50.6
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 1-methyl-N-((3aR,5r,6aS)-2-methyloctahydrocyclopenta[c]pyrrol-5-yl)-N-(3-(trifluoromethoxy)benzyl)-1H-imidazole-4-carboxamide
  参考文献：
  名称：

  An octahydro-cyclopenta[c]pyrrole series of inhibitors of the type 1 glycine transporter

  摘要：

  We describe a novel series of inhibitors of the type 1 glycine transporter (GlyT1) as an approach to relieving the glutamatergic deficit that is thought to underlie schizophrenia. Synthesis and SAR follow-up of a series of octahydro-cyclopenta[c]pyrrole derivatives afforded potent in vitro inhibition of GlyT1 as well as in vivo activity in elevating CSF glycine. We also found that a 3-O(c-pentyl), 4-F substituent may serve as a surrogate for the widely used 3-trifluoromethoxy group, suggesting its application as an isostere for future medicinal chemistry studies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.071

文献信息

• An octahydro-cyclopenta[c]pyrrole series of inhibitors of the type 1 glycine transporter
  作者：John A. Lowe、Shari L. DeNinno、Susan E. Drozda、Christopher J. Schmidt、Karen M. Ward、F. David Tingley、Mark Sanner、Don Tunucci、James Valentine

  DOI：10.1016/j.bmcl.2009.12.071

  日期：2010.2

  We describe a novel series of inhibitors of the type 1 glycine transporter (GlyT1) as an approach to relieving the glutamatergic deficit that is thought to underlie schizophrenia. Synthesis and SAR follow-up of a series of octahydro-cyclopenta[c]pyrrole derivatives afforded potent in vitro inhibition of GlyT1 as well as in vivo activity in elevating CSF glycine. We also found that a 3-O(c-pentyl), 4-F substituent may serve as a surrogate for the widely used 3-trifluoromethoxy group, suggesting its application as an isostere for future medicinal chemistry studies. (C) 2009 Elsevier Ltd. All rights reserved.