| 1160948-03-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• CAS: 1160948-03-7
• 化学式: C₂₂H₂₉NO₄
• 分子量: 371.477
• InChiKey: KBFPWQPWPDHSQU-CIAFKFPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  70.0
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 sodium acetate 、 氯化铵 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of novel triplet drugs with 1,3,5-trioxazatriquinane skeletons and their pharmacologies. Part 2: Synthesis of novel triplet drugs with the epoxymethano structure (capped homotriplet)

  摘要：

  An improved synthetic method for triplet drugs with the 1,3,5-trioxazatriquinane skeleton was developed that used p-toluenesulfonylmethyl isocyanide (TosMIC) instead of 1,3-dithiane. Using the improved method, we synthesized compounds with two identical pharmacophore units and an epoxymethano group, that is, capped homotriplets. Among the synthesized capped homotriplets, KNT-123 showed high selectivity for the p receptor over the kappa receptor, and the mu selectivity was the highest among the reported p selective nonpeptide ligands. KNT-123 administered subcutaneously induced a dose-dependent analgesic effect in the acetic acid writhing assay, and its potency was 11-fold more potent than that of morphine. KNT-123 may serve as a useful tool for the study of the pharmacological actions mediated specifically via the mu receptor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.065
• 作为产物：
  描述：

  (4bR,6S,8aS,9R)-11-(cyclopropylmethyl)-6-(1,3-dithian-2-yl)-3-methoxy-5,6,7,8,9,10-hexahydro-8aH-9,4b-(epiminoethano)phenanthrene-6,8a-diol 在 盐酸 、 copper(II) choride dihydrate 、 水 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of novel triplet drugs with 1,3,5-trioxazatriquinane skeletons and their pharmacologies. Part 2: Synthesis of novel triplet drugs with the epoxymethano structure (capped homotriplet)

  摘要：

  An improved synthetic method for triplet drugs with the 1,3,5-trioxazatriquinane skeleton was developed that used p-toluenesulfonylmethyl isocyanide (TosMIC) instead of 1,3-dithiane. Using the improved method, we synthesized compounds with two identical pharmacophore units and an epoxymethano group, that is, capped homotriplets. Among the synthesized capped homotriplets, KNT-123 showed high selectivity for the p receptor over the kappa receptor, and the mu selectivity was the highest among the reported p selective nonpeptide ligands. KNT-123 administered subcutaneously induced a dose-dependent analgesic effect in the acetic acid writhing assay, and its potency was 11-fold more potent than that of morphine. KNT-123 may serve as a useful tool for the study of the pharmacological actions mediated specifically via the mu receptor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.065

文献信息

• Synthesis of a new opioid ligand having the oxabicyclo[3.2.1]octane skeleton using a new rearrangement reaction
  作者：Akio Watanabe、Hideaki Fujii、Mayumi Nakajima、Ko Hasebe、Hidenori Mochizuki、Hiroshi Nagase

  DOI：10.1016/j.bmcl.2009.03.068

  日期：2009.5

  the 1,3,5-trioxazatriquinane skeleton led to discovery of a novel rearrangement reaction that afforded a compound with an oxabicyclo[3.2.1]octane skeleton whose reaction mechanism was proposed. On the basis of this mechanism, we synthesized the rearranged product from a dimethyl acetal intermediate in excellent yield. The compound with an oxabicyclo[3.2.1]octane skeleton showed high affinity for μ and

  制备具有1,3,5-三氧杂氮杂三喹烷骨架的三聚体的尝试导致发现了新的重排反应，该反应提供了具有氧杂环[3.2.1]辛烷骨架的化合物，提出了其反应机理。基于这种机理，我们以优异的收率从二甲基乙缩醛中间体合成了重排产物。具有氧杂双环[3.2.1]辛烷骨架的化合物显示出对μ和κ的高亲和力，但对δ阿片受体类型没有亲和力。该化合物有望成为新型κ选择性配体的关键中间体。