2-Hydroxy-2-(3-methoxyphenyl)propanal | 1339050-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Hydroxy-2-(3-methoxyphenyl)propanal
• CAS: 1339050-57-5
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: WPSHAMQWHWGQEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-2-(3-methoxyphenyl)propanal 、 2-((4-methoxybenzyl)oxy)-2-phenylpropanal 在 sodium acetate 、 氯化铵 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以66%的产率得到2-(1-((4-Methoxybenzyl)oxy)-1-phenylethyl)-5-(3-methoxyphenyl)-5-methyl-2,5-dihydrooxazole
  参考文献：
  名称：

  由三种不同羰基化合物组成的不对称1,3,5-三恶杂三喹烷衍生物的实用合成

  摘要：

  DOI：

  10.3987/com-18-s(f)65
• 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

文献信息

• Synthesis and Pharmacology of a Novel κ Opioid Receptor (KOR) Agonist with a 1,3,5-Trioxazatriquinane Skeleton
  作者：Shigeto Hirayama、Naohisa Wada、Toru Nemoto、Takashi Iwai、Hideaki Fujii、Hiroshi Nagase

  DOI：10.1021/ml5000542

  日期：2014.8.14

  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.
• The Practical Synthesis of Dissymmetrical 1,3,5-Trioxazatriquinane Derivatives Comprised of Three Distinct Carbonyl Compounds
  作者：Hideaki Fujii、Shigeto Hirayama、Koji Obayashi、Naohisa Wada、Kousuke Ohyama、Shizuho Fuku、Koji Koyano、Fumika Karaki、Kennosuke Itoh、Hiroshi Nagase

  DOI：10.3987/com-18-s(f)65

  日期：——
• 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)
  作者：Hiroshi Nagase、Koji Koyano、Naohisa Wada、Shigeto Hirayama、Akio Watanabe、Toru Nemoto、Mayumi Nakajima、Kaoru Nakao、Hidenori Mochizuki、Hideaki Fujii

  DOI：10.1016/j.bmcl.2011.07.065

  日期：2011.10

  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.