17,17'-bis(cyclopropylmethyl)-6,6',7,7'-tetrahydro-4,5:4',5'-diepoxy-6,6'-(benzylimino)[7,7'-bimorphinan]-3,3',14,14'-tetrol

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 17,17'-bis(cyclopropylmethyl)-6,6',7,7'-tetrahydro-4,5:4',5'-diepoxy-6,6'-(benzylimino)[7,7'-bimorphinan]-3,3',14,14'-tetrol
• 英文别名: (1S,2S,7S,8S,12R,20R,24R,32R)-22-benzyl-11,33-bis(cyclopropylmethyl)-19,25-dioxa-11,22,33-triazaundecacyclo[24.9.1.18,14.01,24.02,32.04,23.05,21.07,12.08,20.030,36.018,37]heptatriaconta-4(23),5(21),14(37),15,17,26,28,30(36)-octaene-2,7,17,27-tetrol
• 化学式: C₄₇H₄₉N₃O₆
• 分子量: 751.923
• InChiKey: YFEFMSMEIWBCRN-CLLGMEHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  56
• 可旋转键数：
  6
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Benzyl-hydrazine; compound with sulfuric acid 、 纳曲酮 在 溶剂黄146 作用下， 以20%的产率得到(4R,4aS,7aR,12bS)-7-[2-[(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]hydrazinyl]-3-(cyclopropylmethyl)-1,2,4,5,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol
  参考文献：
  名称：

  Major Effect of Pyrrolic N-Benzylation in Norbinaltorphimine, the Selective κ-Opioid Receptor Antagonist

  摘要：

  Indolic N-benzylation of naltrindole reportedly extends the duration of delta-opioid receptor (DOR) antagonism. Similar modification of the kappa-opioid receptor (KOR) antagonist norBNI (1a) and its 17,17'-diNMe analogue (1d), a low potency mu-opioid receptor (MOR) partial agonist, was found to affect predominantly their MOR activity. When administered systemically in mouse antinociceptive assays, N-benzyl-norBNI (1b) had only MOR agonist activity of relatively short duration whereas on central administration it had only a KOR-antagonist action of extremely long duration.

  DOI：

  10.1021/jm049172n

文献信息

• Major Effect of Pyrrolic N-Benzylation in Norbinaltorphimine, the Selective κ-Opioid Receptor Antagonist
  作者：Cédric Chauvignac、Carl N. Miller、Sanjay K. Srivastava、John W. Lewis、Stephen M. Husbands、John R. Traynor

  DOI：10.1021/jm049172n

  日期：2005.3.1

  Indolic N-benzylation of naltrindole reportedly extends the duration of delta-opioid receptor (DOR) antagonism. Similar modification of the kappa-opioid receptor (KOR) antagonist norBNI (1a) and its 17,17'-diNMe analogue (1d), a low potency mu-opioid receptor (MOR) partial agonist, was found to affect predominantly their MOR activity. When administered systemically in mouse antinociceptive assays, N-benzyl-norBNI (1b) had only MOR agonist activity of relatively short duration whereas on central administration it had only a KOR-antagonist action of extremely long duration.