2-[(2-吡啶基甲基)硫代]-1H-苯并咪唑-5-磺基酸 | 81919-18-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 2-[(2-吡啶基甲基)硫代]-1H-苯并咪唑-5-磺基酸
• 英文名称: 1,8-bis(β-naltrexamino)-3,6-dioxaoctane
• 英文别名: Tena；(4R,4aS,7R,7aR,12bS)-7-[2-[2-[2-[[(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]amino]ethoxy]ethoxy]ethylamino]-3-(cyclopropylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol
• CAS: 81919-18-8
• 化学式: C₄₆H₆₂N₄O₈
• 分子量: 799.02
• InChiKey: OPDFUQJBZZJZRG-WPJYNPJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  58
• 可旋转键数：
  15
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  148
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (5alpha,6beta)-6-氨基-17-(环丙基甲基)-4,5-环氧-吗喃-3,14-二醇 、 三乙二醇二(对甲苯磺酸酯) 在 sodium carbonate 作用下， 以 二乙二醇二甲醚 、 甲苯 为溶剂， 反应 3.0h， 以60%的产率得到2-[(2-吡啶基甲基)硫代]-1H-苯并咪唑-5-磺基酸
  参考文献：
  名称：

  Narcotic antagonistic potency of bivalent ligands which contain .beta.-naltrexamine. Evidence for simultaneous occupation of proximal recognition sites

  摘要：

  Two-bivalent ligands (P-X-P) containing the beta-naltrexamine pharmacophore (P) and a connecting oligoethylene glycol spanner (X) were synthesized and evaluated for narcotic antagonistic activity in the guinea pig ileum (GPI) and mouse vas deferens (MVD). The bivalent ligand 2 whose spanner contains three ethylene units possessed 10-fold greater antagonistic potency than its monovalent analogue (4) in antagonizing the effects of ethylketazocine (EK) on the GPI, while no differential antagonism of morphine was observed among the compounds. In the MVD, 2 was not substantially more potent than 4 as an antagonist against [D-Ala2,D-Leu5]enkephalin (DADLE). The bivalent ligand 3, whose spanner contains six ethylene units, exhibited 15 times greater potency in antagonizing the agonist effects of DADLE on the MVD than its monovalent ligand 4. No marked increase in the ability of 3 to antagonize the effects of morphine or EK on the GPI was observed. The data indicate that mu, kappa, and delta opioid receptors exhibit different selectivity toward bivalent ligands whose spanner lengths differ. The enhanced potency associated with different receptor interactions is consistent with simultaneous occupation of proximal recognition sites. Whether such proximal recognition sites are identical or different remains to be clarified. The distance between proximal sites appears to depend on the opioid receptor subtype involved.

  DOI：

  10.1021/jm00349a016