N-((2R,6R,11R)-3-Cyclopropylmethyl-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl)-formamide

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 6,7-苯并吗啡烷
• 英文名称: N-((2R,6R,11R)-3-Cyclopropylmethyl-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl)-formamide
• 英文别名: N-[10-(cyclopropylmethyl)-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-yl]formamide
• 化学式: C₁₉H₂₆N₂O
• 分子量: 298.428
• InChiKey: GRERSJXDCJKLDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-((2R,6R,11R)-3-Cyclopropylmethyl-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl)-formamide 、 碘甲烷 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 以79%的产率得到N-((2R,6R,11R)-3-Cyclopropylmethyl-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl)-N-methyl-formamide
  参考文献：
  名称：

  Redefining the structure–activity relationships of 2,6-methano-3-benzazocines. Part 2: 8-formamidocyclazocine analogues

  摘要：

  High affinity binding for p and K opioid receptors has been observed in analogues of cyclazocine, ethylketocyclazocine and naltrexone where the prototypic (of opiates) phenolic OH group was replaced with a formamide (-NHCHO) group. For the 8-formamide analogue of cyclazocine, binding is highly enantiospecific (eudismic ratios similar to2000 for mu and kappa) with K-i values less than or equal to 1 nM observed for the (2R,6R, 11R)-isomer, (-)-4. A preliminary SAR revealed that affinity is very sensitive to substitution on the formamide appendage. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00295-6
• 作为产物：
  描述：

  甲酸 、 8-amino-3-(cyclopropylmethyl)-1,2,3,4,5,6-hexahydro-cis-6,11-dimethyl-2,6-methano-3-benzazocine 反应 14.0h， 以65%的产率得到N-((2R,6R,11R)-3-Cyclopropylmethyl-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl)-formamide
  参考文献：
  名称：

  8-substituted-2,6-methano-3-benzazocines and 3-substituted morphinanes as opioid receptor binding agents

  摘要：

  公开号：

  EP1944292B9

文献信息

• 8-substituted-2,6-methano-3-benzazocines and 3-substituted morphinanes as opioid receptor binding agents
  申请人：RENSSELAER POLYTECHNIC INSTITUTE

  公开号：EP1944292B9

  公开（公告）日：2016-07-06
• Redefining the structure–activity relationships of 2,6-methano-3-benzazocines. Part 2: 8-formamidocyclazocine analogues
  作者：Mark P. Wentland、Xufeng Sun、Yingchun Ye、Rongliang Lou、Jean M. Bidlack

  DOI：10.1016/s0960-894x(03)00295-6

  日期：2003.6

  High affinity binding for p and K opioid receptors has been observed in analogues of cyclazocine, ethylketocyclazocine and naltrexone where the prototypic (of opiates) phenolic OH group was replaced with a formamide (-NHCHO) group. For the 8-formamide analogue of cyclazocine, binding is highly enantiospecific (eudismic ratios similar to2000 for mu and kappa) with K-i values less than or equal to 1 nM observed for the (2R,6R, 11R)-isomer, (-)-4. A preliminary SAR revealed that affinity is very sensitive to substitution on the formamide appendage. (C) 2003 Elsevier Science Ltd. All rights reserved.