(2'R,5α,6R,7R,14α)-2'-(1-chloro-17-cyclopropylmethyl-7,8-dihydro-4,5-epoxy-6,14-ethano-3-hydroxy-6-methoxy-morphinan-7-yl)-3',3'-dimethylbutan-2'-ol hydrochloride | 1333904-18-9

• 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: (2'R,5α,6R,7R,14α)-2'-(1-chloro-17-cyclopropylmethyl-7,8-dihydro-4,5-epoxy-6,14-ethano-3-hydroxy-6-methoxy-morphinan-7-yl)-3',3'-dimethylbutan-2'-ol hydrochloride
• 英文别名: 1-chlorobuprenorphine；(1S,2S,6R,14R,15R,16R)-9-chloro-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8,10,12(20)-trien-11-ol;hydrochloride
• CAS: 1333904-18-9
• 化学式: C₂₉H₄₀ClNO₄*ClH
• 分子量: 538.555
• InChiKey: MZJHQIVHLFXVLL-RZIPZOSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  62.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2'R,5α,6R,7R,14α)-2'-(1-chloro-17-cyclopropylmethyl-7,8-dihydro-3,6-dimethoxy-4,5-epoxy-6,14-ethano-morphinan-7-yl)-3',3'-dimethylbutan-2'-ol 在 丙烷-1-硫醇 、 sodium hydride 、 盐酸 作用下， 以 六甲基磷酰三胺 、 乙醚 、 异丙醇 为溶剂， 反应 3.0h， 以56%的产率得到(2'R,5α,6R,7R,14α)-2'-(1-chloro-17-cyclopropylmethyl-7,8-dihydro-4,5-epoxy-6,14-ethano-3-hydroxy-6-methoxy-morphinan-7-yl)-3',3'-dimethylbutan-2'-ol hydrochloride
  参考文献：
  名称：

  Structural Determinants of Opioid and NOP Receptor Activity in Derivatives of Buprenorphine

  摘要：

  The unique pharmacological profile of buprenorphine has led to its considerable success as an analgesic and as a treatment agent for drug abuse. Activation of nociceptin/orphanin FQ peptide (NOP) receptors has been postulated to account for certain aspects of buprenorphine's behavioral profile. In order to investigate the role of NOP activation further, a series of buprenorphine analogues has been synthesized with the aim of increasing affinity for the NOP receptor. Binding and functional assay data on these new compounds indicate that the area around C20 in the orvinols is key to NOP receptor activity, with several compounds displaying higher affinity than buprenorphine. One compound, 1b, was found to be a mu opioid receptor partial agonist of comparable efficacy to buprenorphine but with higher efficacy at NOP receptors.

  DOI：

  10.1021/jm2003238