[5-(3-phenylpropoxy)oxolan-3-yl]methyl N-(pyridin-2-ylmethyl)carbamate | 132183-97-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: [5-(3-phenylpropoxy)oxolan-3-yl]methyl N-(pyridin-2-ylmethyl)carbamate
• CAS: 132183-97-2；132184-14-6
• 化学式: C₂₁H₂₆N₂O₄
• 分子量: 370.448
• InChiKey: AONBRXOBRGSEHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [5-(3-phenylpropoxy)oxolan-3-yl]methyl N-(pyridin-2-ylmethyl)carbamate 、 乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  4-Substituted 2-alkoxytetrahydrofurans as potent and long-lasting PAF antagonists

  摘要：

  A series of 4-substituted 2-alkoxytetrahydrofuran derivatives featuring an acetal group were prepared and evaluated for PAF antagonist activity in the PAF-induced in vitro platelet-aggregation and in vivo hypotension tests. Compound 2-[[N-acetyl-N-[[[2-(octadecyloxy)tetrahydrofuran-4-yl]methoxy]carbonyl]amino]methyl]1-ethylpyridinium chloride (4e, UR-11353) was selected for further development on the basis of its high activity and long-lasting action. The compound maintained a significant activity even 24 h after administration of a single dose of 1 mg/kg iv in the PAF-induced mortality test in mice and 10 h after administration of the same dose in the PAF-induced hypotension test in rats. Comparison with previously reported carba analogues suggests that the presence of the acetal group is the structural characteristic that confers its long-lasting activity.

  DOI：

  10.1021/jm00082a007
• 作为产物：
  描述：

  4-<<(phenoxycarbonyl)oxy>methyl>-2-methoxytetrahydrofuran 在 Dowex HCR-S-H⁺ 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 55.0h， 生成 [5-(3-phenylpropoxy)oxolan-3-yl]methyl N-(pyridin-2-ylmethyl)carbamate
  参考文献：
  名称：

  4-Substituted 2-alkoxytetrahydrofurans as potent and long-lasting PAF antagonists

  摘要：

  A series of 4-substituted 2-alkoxytetrahydrofuran derivatives featuring an acetal group were prepared and evaluated for PAF antagonist activity in the PAF-induced in vitro platelet-aggregation and in vivo hypotension tests. Compound 2-[[N-acetyl-N-[[[2-(octadecyloxy)tetrahydrofuran-4-yl]methoxy]carbonyl]amino]methyl]1-ethylpyridinium chloride (4e, UR-11353) was selected for further development on the basis of its high activity and long-lasting action. The compound maintained a significant activity even 24 h after administration of a single dose of 1 mg/kg iv in the PAF-induced mortality test in mice and 10 h after administration of the same dose in the PAF-induced hypotension test in rats. Comparison with previously reported carba analogues suggests that the presence of the acetal group is the structural characteristic that confers its long-lasting activity.

  DOI：

  10.1021/jm00082a007

文献信息

• New 4-substituted 2-alkoxytetrahydrofuran derivatives
  申请人：J. URIACH & CIA. S.A.

  公开号：EP0381098A2

  公开（公告）日：1990-08-08

  The present invention describes a process to obtain 4-substituted 2-­alkoxytetrahydrofuran derivatives of formula I. wherein, -R₁ represents an alkyl or phenylalkyl radical; -R₂ is hydrogen, C₁-C₄-acyl or C₁-C₄-alkoxycarbonyl; -R₃ is either an electron pair, in which case t means nothing and q is zero, or R₃ is hydrogen or C₁-C₄-alkyl, in which case t is (+) and q=1;.A⁻ is a pharmaceutically acceptable anion. These compounds are antagonists of PAF and, therefore, useful for the treatment of the diseases in which this substance is involved

  本发明描述了一种获得式 I 的 4-取代的 2-烷氧基四氢呋喃衍生物的工艺。 其中 -R₁代表烷基或苯基烷基； -R₂是氢、C₁-C₄-酰基或 C₁-C₄-烷氧基羰基；-R₃或者是电子对，在这种情况下，t 表示无，q 为零，或者 R₃ 是氢或 C₁-C₄- 烷基，在这种情况下，t 为 (+)，q=1；。A- 是药学上可接受的阴离子。这些化合物是 PAF 的拮抗剂，因此可用于治疗与 PAF 有关的疾病。
• 4-Substituted 2-alkoxytetrahydrofurans as potent and long-lasting PAF antagonists
  作者：Elena Carceller、Manuel Merlos、Marta Giral、Javier Bartroli、Julian Garcia-Rafanell、Javier Forn

  DOI：10.1021/jm00082a007

  日期：1992.2

  A series of 4-substituted 2-alkoxytetrahydrofuran derivatives featuring an acetal group were prepared and evaluated for PAF antagonist activity in the PAF-induced in vitro platelet-aggregation and in vivo hypotension tests. Compound 2-[[N-acetyl-N-[[[2-(octadecyloxy)tetrahydrofuran-4-yl]methoxy]carbonyl]amino]methyl]1-ethylpyridinium chloride (4e, UR-11353) was selected for further development on the basis of its high activity and long-lasting action. The compound maintained a significant activity even 24 h after administration of a single dose of 1 mg/kg iv in the PAF-induced mortality test in mice and 10 h after administration of the same dose in the PAF-induced hypotension test in rats. Comparison with previously reported carba analogues suggests that the presence of the acetal group is the structural characteristic that confers its long-lasting activity.