t-butyl N-[(17-cyclopropylmethyl-6β,14β-epoxy-3-methoxymorphinan-6α-yl)methyl]carbamate | 1130020-83-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: t-butyl N-[(17-cyclopropylmethyl-6β,14β-epoxy-3-methoxymorphinan-6α-yl)methyl]carbamate
• CAS: 1130020-83-5
• 化学式: C₂₇H₃₈N₂O₄
• 分子量: 454.61
• InChiKey: KYECVVUXTAVQKM-UUSJWDGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  60.03
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  t-butyl N-[(17-cyclopropylmethyl-6β,14β-epoxy-3-methoxymorphinan-6α-yl)methyl]carbamate 在 盐酸 、 水 、 1,8-双二甲氨基萘 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.67h， 生成 N-[(17-benzyl-6β,14β-epoxy-3-methoxymorphinan-6α-yl)methyl]-4-methoxybenzamide
  参考文献：
  名称：

  Synthesis of 6,14-epoxymorphinan derivatives and their pharmacologies

  摘要：

  A novel 6,14-epoxymorphinan benzamide derivative (NS22) that was previously reported showed opioid kappa receptor agonistic activity and analgesic activity. The unsatisfactory kappa selectivity of NS22 led us to synthesize its derivatives to improve the opioid kappa receptor selectivity and the agonist activity. In the course of SAR of the various derivatives, 17-benzyl-6,14-epoxymorphinan derivatives (KNT-33, 53, 55, 80, 90, 133) were found to show high selectivities and affinities for the opioid kappa receptor. In addition, KNT-33, 53, 55 showed dose-dependent analgesic effects in acetic acid writhing tests. Therefore, 17-benzyl substituents may play an important role for developing kappa selectivity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.035
• 作为产物：
  描述：

  (4bR,6R,8aS,9R)-6-(azidomethyl)-11-(cyclopropylmethyl)-3-methoxy-5,6,7,8,9,10-hexahydro-9,4b-(epiminoethano)-6,8a-epoxyphenanthrene 在 吡啶 、 palladium 10% on activated carbon 、 camphor-10-sulfonic acid 、 氢气 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 t-butyl N-[(17-cyclopropylmethyl-6β,14β-epoxy-3-methoxymorphinan-6α-yl)methyl]carbamate
  参考文献：
  名称：

  Synthesis of 6,14-epoxymorphinan derivatives and their pharmacologies

  摘要：

  A novel 6,14-epoxymorphinan benzamide derivative (NS22) that was previously reported showed opioid kappa receptor agonistic activity and analgesic activity. The unsatisfactory kappa selectivity of NS22 led us to synthesize its derivatives to improve the opioid kappa receptor selectivity and the agonist activity. In the course of SAR of the various derivatives, 17-benzyl-6,14-epoxymorphinan derivatives (KNT-33, 53, 55, 80, 90, 133) were found to show high selectivities and affinities for the opioid kappa receptor. In addition, KNT-33, 53, 55 showed dose-dependent analgesic effects in acetic acid writhing tests. Therefore, 17-benzyl substituents may play an important role for developing kappa selectivity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.035