N-cyano-6,14-endoethano-7α-(1-(R)-hydroxy-1-cyclopropyl-ethyl)-tetrahydronorthebaine | 201011-78-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N-cyano-6,14-endoethano-7α-(1-(R)-hydroxy-1-cyclopropyl-ethyl)-tetrahydronorthebaine
• 英文别名: (1S,2S,6R,14R,15R,16R)-16-[(1R)-1-cyclopropyl-1-hydroxyethyl]-11,15-dimethoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-triene-5-carbonitrile
• CAS: 201011-78-1
• 化学式: C₂₆H₃₂N₂O₄
• 分子量: 436.551
• InChiKey: RYQVAKRDJHUOKK-IFABYKJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  74.95
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-cyano-6,14-endoethano-7α-(1-(R)-hydroxy-1-cyclopropyl-ethyl)-tetrahydronorthebaine 在 氢氧化钾 、 magnesium acetate 作用下， 以 N,N-二甲基甲酰胺 、 二乙二醇 为溶剂， 反应 7.5h， 生成 N-cyclobutylmethyl-6,14-endoethano-7α-(1-(R)-hydroxy-1-cyclopropyl-ethyl)-tetrahydronorthebaine
  参考文献：
  名称：

  A highly selective κ-opioid receptor agonist with low addictive potential and dependence liability

  摘要：

  Buprenorphine analogs have been synthesized. In the studies of analgesic and addictive effects in mice and [S-35]GTP gamma S binding assay in human brain tissue, an analog of buprenorphine where the tert-butyl is replaced by a cyclobutyl moiety (16) has been identified as a selective K-partial agonist which gives antinociceptive effects, but has low abuse potential. The results may lead to lower degrees of dysphoria than full K-agonists. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.017
• 作为产物：
  描述：

  1-[(5alpha,7alpha)-4,5-环氧-3,6-二甲氧基-17-甲基-6,14-乙烯桥吗喃-7-基]乙酮 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 30.0 ℃ 、413.68 kPa 条件下， 反应 25.5h， 生成 N-cyano-6,14-endoethano-7α-(1-(R)-hydroxy-1-cyclopropyl-ethyl)-tetrahydronorthebaine
  参考文献：
  名称：

  A highly selective κ-opioid receptor agonist with low addictive potential and dependence liability

  摘要：

  Buprenorphine analogs have been synthesized. In the studies of analgesic and addictive effects in mice and [S-35]GTP gamma S binding assay in human brain tissue, an analog of buprenorphine where the tert-butyl is replaced by a cyclobutyl moiety (16) has been identified as a selective K-partial agonist which gives antinociceptive effects, but has low abuse potential. The results may lead to lower degrees of dysphoria than full K-agonists. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.017