3,6-Bis(3-methoxyphenyl)-3,6-dimethyl-1,4-dioxane-2,5-diol | 1339050-59-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,6-Bis(3-methoxyphenyl)-3,6-dimethyl-1,4-dioxane-2,5-diol
• 英文别名: 3,6-bis(3-methoxyphenyl)-3,6-dimethyl-1,4-dioxane-2,5-diol
• CAS: 1339050-59-7
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: UKGIOUGILBMEKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-2-(3-methoxyphenyl)propanal 、 1-(3-methoxyphenyl)-1-[5-(3-methoxyphenyl)-5-methyl-2H-1,3-oxazol-2-yl]ethanol 、 3,6-Bis(3-methoxyphenyl)-3,6-dimethyl-1,4-dioxane-2,5-diol 在 D(+)-10-樟脑磺酸 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以15%的产率得到2,4,6-tris(3-methoxyphenyl)-2,4,6-trimethyl-1,3,5-trioxazatriquinane
  参考文献：
  名称：

  Synthesis and Pharmacology of a Novel κ Opioid Receptor (KOR) Agonist with a 1,3,5-Trioxazatriquinane Skeleton

  摘要：

  We designed and synthesized the 1,3,5-trioxazatriquinane derivatives with m-hydroxyphenyl groups. These compounds include the phenethylamine structure within them, which is a common structure observed in morphinan derivatives like morphine. Among the synthesized compounds, (-)-8c with two m-hydroxyphenyl groups selectively bound and exerted full agonist activity toward the κ opioid receptor (KOR). Subcutaneously administered (-)-8c exhibited significant antinociceptive effects via the KOR in a dose-dependent manner. These results suggest the emergence of a novel class of KOR agonist.

  DOI：

  10.1021/ml5000542
• 作为产物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 2-Hydroxy-2-(3-methoxyphenyl)propanal 、 3,6-Bis(3-methoxyphenyl)-3,6-dimethyl-1,4-dioxane-2,5-diol
  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