(4S,1'R)-4-(1'-naphthalene-2-yl-ethylcarbamoyl)-2-aza-spiro<4.5>decane-2,4-dicarboxylic acid benzyl ester | 235791-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (4S,1'R)-4-(1'-naphthalene-2-yl-ethylcarbamoyl)-2-aza-spiro<4.5>decane-2,4-dicarboxylic acid benzyl ester
• 英文别名: benzyl (4S)-4-[[(1R)-1-naphthalen-2-ylethyl]carbamoyl]-2-azaspiro[4.5]decane-2-carboxylate
• CAS: 235791-25-0
• 化学式: C₃₀H₃₄N₂O₃
• 分子量: 470.612
• InChiKey: GEUZZQQJQUGFTL-AMGIVPHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,1'R)-4-(1'-naphthalene-2-yl-ethylcarbamoyl)-2-aza-spiro<4.5>decane-2,4-dicarboxylic acid benzyl ester 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到(S)-2-azaspiro[4.5]decane-4-carboxylic acid hydrochloride
  参考文献：
  名称：

  An in vitro investigation into conformational aspects of gabapentin

  摘要：

  Conformational analysis of constrained cyclohexane systems was pioneered fifty years ago by Barton and Hassel. We now report an investigation based on a conformational analysis of a number of novel cyclohexane based Gabapentin analogues coupled with their in vitro evaluation at the Gabapentin binding site. These data are used to propose a possible binding conformation for Gabapentin. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00023-1
• 作为产物：
  描述：

  2-aza-spiro<4.5>decane-2,4-dicarboxylic acid 2-benzyl ester 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 (4S,1'R)-4-(1'-naphthalene-2-yl-ethylcarbamoyl)-2-aza-spiro<4.5>decane-2,4-dicarboxylic acid benzyl ester
  参考文献：
  名称：

  An in vitro investigation into conformational aspects of gabapentin

  摘要：

  Conformational analysis of constrained cyclohexane systems was pioneered fifty years ago by Barton and Hassel. We now report an investigation based on a conformational analysis of a number of novel cyclohexane based Gabapentin analogues coupled with their in vitro evaluation at the Gabapentin binding site. These data are used to propose a possible binding conformation for Gabapentin. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00023-1

文献信息

• Synthesis and biological evaluation of conformationally restricted gabapentin analogues
  作者：Jean-Marie Receveur、Justin S. Bryans、Mark J. Field、Lakhbir Singh、David C. Horwell

  DOI：10.1016/s0960-894x(99)00383-2

  日期：1999.8

  A series of conformationally restricted Gabapentin analogues has been synthesised. The pyrrolidine analogue (R)-2-Aza-spiro[4.5]decane-4-carboxylic acid hydrochloride (3a) had an IC(50) of 120nM, similar to that of Gabapentin (IC(50) = 140nM), at the Gabapentin binding site on the alpha(2)delta subunit of a calcium channel. Compound (3a) also reversed carrageenan induced hyperalgesia in rats, (C) 1999 Elsevier Science Ltd. All rights reserved.