tert-butyl 5-[(R)-[(2S,5R)-4-benzyl-2,5-dimethylpiperazinyl](3-methoxyphenyl)methyl]-1,3-dihydro-2H-isoindole-2-carboxylate | 253801-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: tert-butyl 5-[(R)-[(2S,5R)-4-benzyl-2,5-dimethylpiperazinyl](3-methoxyphenyl)methyl]-1,3-dihydro-2H-isoindole-2-carboxylate
• 英文别名: tert-butyl 5-[(R)-[(2S,5R)-4-benzyl-2,5-dimethylpiperazin-1-yl]-(3-methoxyphenyl)methyl]-1,3-dihydroisoindole-2-carboxylate
• CAS: 253801-16-0
• 化学式: C₃₄H₄₃N₃O₃
• 分子量: 541.734
• InChiKey: ZYQIEFXCJZRFBI-NPPPIGHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  45.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-[(R)-[(2S,5R)-4-benzyl-2,5-dimethylpiperazinyl](3-methoxyphenyl)methyl]-1,3-dihydro-2H-isoindole-2-carboxylate 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 生成 5-[(R)-[(2S,5R)-4-benzyl-2,5-dimethylpiperazin-1-yl]-(3-methoxyphenyl)methyl]-2,3-dihydro-1H-isoindole
  参考文献：
  名称：

  Highly potent and selective zwitterionic agonists of the δ-opioid receptor. Part 1

  摘要：

  A series of zwitterionic delta-opioid agonists, with targeted physicochemistry, as a strategy to limit potential for CNS exposure, were prepared. These agents were found to possess exquisite potency and selectivity over mu and K-opiate activity. Furthermore, analogue 3a was found to display restricted CNS exposure, as evidenced by its inactivity in a rodent hyperlocomotion assay of central opiate activity. Dog pharmacokinetic studies on 3a indicated encouraging oral bioavailability. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.102
• 作为产物：
  描述：

  5-甲酰基异吲哚啉-2-羧酸叔丁酯 、 (3-methoxyphenyl)magnesium bromide 、 (+/-)-trans-2,5-dimethyl-4-benzyl-piperazine 在 T406石油添加剂 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 反应 4.0h， 生成 tert-butyl 5-[(R)-[(2S,5R)-4-benzyl-2,5-dimethylpiperazinyl](3-methoxyphenyl)methyl]-1,3-dihydro-2H-isoindole-2-carboxylate
  参考文献：
  名称：

  Highly potent and selective zwitterionic agonists of the δ-opioid receptor. Part 1

  摘要：

  A series of zwitterionic delta-opioid agonists, with targeted physicochemistry, as a strategy to limit potential for CNS exposure, were prepared. These agents were found to possess exquisite potency and selectivity over mu and K-opiate activity. Furthermore, analogue 3a was found to display restricted CNS exposure, as evidenced by its inactivity in a rodent hyperlocomotion assay of central opiate activity. Dog pharmacokinetic studies on 3a indicated encouraging oral bioavailability. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.102

文献信息

• US6200978B1
  申请人：——

  公开号：US6200978B1

  公开（公告）日：2001-03-13
• Highly potent and selective zwitterionic agonists of the δ-opioid receptor. Part 1
  作者：Donald S. Middleton、Graham N. Maw、Clare Challenger、Alan Jessiman、Patrick S. Johnson、William A. Million、Carly L. Nichols、Jenny A. Price、Michael Trevethick

  DOI：10.1016/j.bmcl.2005.10.102

  日期：2006.2

  A series of zwitterionic delta-opioid agonists, with targeted physicochemistry, as a strategy to limit potential for CNS exposure, were prepared. These agents were found to possess exquisite potency and selectivity over mu and K-opiate activity. Furthermore, analogue 3a was found to display restricted CNS exposure, as evidenced by its inactivity in a rodent hyperlocomotion assay of central opiate activity. Dog pharmacokinetic studies on 3a indicated encouraging oral bioavailability. (c) 2005 Elsevier Ltd. All rights reserved.