1-phthalimido-8-(β-naltrexamino)-3,6-dioxaoctane | 101858-67-7

• 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: 1-phthalimido-8-(β-naltrexamino)-3,6-dioxaoctane
• CAS: 101858-67-7
• 化学式: C₃₄H₄₁N₃O₇
• 分子量: 603.715
• InChiKey: LHWJYYAEYBOMHL-ZJHWPQAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  120.8
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  2-{2-[2-(2-羟基乙氧基)乙氧基]乙基}-1H-异吲哚-1,3(2H)-二酮 在 吡啶 、 碳酸氢钠 作用下， 以 二乙二醇二甲醚 、 甲苯 为溶剂， 反应 35.0h， 生成 1-phthalimido-8-(β-naltrexamino)-3,6-dioxaoctane
  参考文献：
  名称：

  Investigation of the structural requirements for the .kappa.-selective opioid receptor antagonist 6.beta.,6.beta.'-[ethylenebis(oxyethyleneimino)]bis[17-(cyclopropylmethyl)-4,5.alpha.-epoxymorphinan-3,14-diol](TENA)

  摘要：

  In an effort to determine whether or not the basic nitrogens in the spacer of the bivalent ligand 6 beta,6 beta'-[ethylenebis(oxyethyleneimino)]bis[17-(cyclopropylmethyl)4,5 alpha-epoxymorphinan-3,14-diol] (TENA, 1) is responsible for its selective kappa opioid antagonist activity, we have synthesized monovalent analogues 2-4 that contain a C-6 side chain with basic nitrogens. Analogue 2 behaved as a potent opioid agonist in the guinea pig ileum preparation (GPI) and possessed no significant kappa opioid antagonist activity (IC50 ratio = 1) relative to TENA (IC50 ratio = 20). The agonist activity of 3 and 4 interfered with the opioid antagonist assay and therefore did not permit evaluation of antagonist activity in a concentration range where TENA is effective. Although the results obtained with 2 are consistent with the requirement of a second opiate pharmacophore (rather than a second basic nitrogen in the spacer) for the kappa antagonist activity of TENA, the potent agonism associated with these monomers do not allow a firm conclusion in this regard.

  DOI：

  10.1021/jm00155a048