14β-benzyloxy-17-cyclopropylmethyl-4,5α-epoxy-3-hydroxy-6β-(cinnamoylamino)morphinan | 1137990-45-4

• 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: 14β-benzyloxy-17-cyclopropylmethyl-4,5α-epoxy-3-hydroxy-6β-(cinnamoylamino)morphinan
• 英文别名: (2E)-N-[(1S,5R,13R,14R,17S)-17-(benzyloxy)-4-(cyclopropylmethyl)-10-hydroxy-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-yl]-3-phenylprop-2-enamide；(E)-N-[(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-9-hydroxy-4a-phenylmethoxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]-3-phenylprop-2-enamide
• CAS: 1137990-45-4
• 化学式: C₃₆H₃₈N₂O₄
• 分子量: 562.709
• InChiKey: NBNXLAMYDYEUPQ-ZUXJCJRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  14β-benzyloxy-17-cyclopropylmethyl-4,5α-epoxy-3-methoxy-6β-(cinnamoylamino)morphinan 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以18%的产率得到14β-benzyloxy-17-cyclopropylmethyl-4,5α-epoxy-3-hydroxy-6β-(cinnamoylamino)morphinan
  参考文献：
  名称：

  Mixed κ/μ Opioid Receptor Agonists: The 6β-Naltrexamines

  摘要：

  Ligands from the naltrexamine series have consistently demonstrated agonist activity at kappa opioid receptors (KOR), with varying activity at the mu opioid receptor (MOR). Various 6 beta-cinnamoylamino derivatives were made with the aim of generating ligands with a KOR agonist/MOR partial agonist profile, as ligands with this activity may be of interest as treatment agents for cocaine abuse. The ligands all displayed the desired high affinity, nonselective binding in vitro and in the functional assays were high efficacy KOR agonists with some partial agonist activity at MOR. Two of the new ligands (12a, 12b) have been evaluated in vivo, with 12a acting as a KOR agonist and therefore somewhat similar to the previously evaluated analogues 3-6, while 12b displayed predominant MOR agonist activity.

  DOI：

  10.1021/jm8015552

文献信息

• Mixed κ/μ Opioid Receptor Agonists: The 6β-Naltrexamines
  作者：Gerta Cami-Kobeci、Adrian P. Neal、Faye A. Bradbury、Lauren C. Purington、Mario D. Aceto、Louis S. Harris、John W. Lewis、John R. Traynor、Stephen M. Husbands

  DOI：10.1021/jm8015552

  日期：2009.3.26

  Ligands from the naltrexamine series have consistently demonstrated agonist activity at kappa opioid receptors (KOR), with varying activity at the mu opioid receptor (MOR). Various 6 beta-cinnamoylamino derivatives were made with the aim of generating ligands with a KOR agonist/MOR partial agonist profile, as ligands with this activity may be of interest as treatment agents for cocaine abuse. The ligands all displayed the desired high affinity, nonselective binding in vitro and in the functional assays were high efficacy KOR agonists with some partial agonist activity at MOR. Two of the new ligands (12a, 12b) have been evaluated in vivo, with 12a acting as a KOR agonist and therefore somewhat similar to the previously evaluated analogues 3-6, while 12b displayed predominant MOR agonist activity.