KNT-2 | 1130021-10-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: KNT-2
• 英文别名: N-[(17-cyclopropylmethyl-6β,14β-epoxy-3-hydroxymorphinan-6α-yl)methyl]-N-methylbenzamide
• CAS: 1130021-10-1
• 化学式: C₂₉H₃₄N₂O₃
• 分子量: 458.601
• InChiKey: VVJCVMDRMJXXII-YXINZVNLSA-N

物化性质

• 沸点：
  654.5±55.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  53.01
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  KNT-2 在 盐酸 作用下， 以 甲醇 为溶剂， 以59%的产率得到KNT-2 hydrochloride
  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 、 丙烷-1-硫醇 、 palladium 10% on activated carbon 、 camphor-10-sulfonic acid 、 potassium tert-butylate 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 15.5h， 生成 KNT-2
  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