[2-(1-chloroethyl)-[1,3]dioxolan-4-yl]methanol | 857785-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: [2-(1-chloroethyl)-[1,3]dioxolan-4-yl]methanol
• 英文别名: [2-(1-Chloroethyl)-1,3-dioxolan-4-yl]methanol；[2-(1-chloroethyl)-1,3-dioxolan-4-yl]methanol
• CAS: 857785-13-8
• 化学式: C₆H₁₁ClO₃
• 分子量: 166.605
• InChiKey: BERSFIHQWZMYOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [2-(1-chloroethyl)-[1,3]dioxolan-4-yl]methanol 在 potassium hydroxide 作用下， 以61%的产率得到4-methyl-3,6,8-trioxabicyclo[3.2.1]octane
  参考文献：
  名称：

  Properly substituted 1,4-dioxane nucleus favours the selective M3 muscarinic receptor activation

  摘要：

  Novel analogues of cis-N,N,N-trimethyl-(6-methyl-1,4-dioxan-2-yl)methanaminium iodide (2a) were synthesized by inserting methyl groups alternatively or simultaneously in positions 5 and 6 of the 1,4-dioxane nucleus in all combinations. Their biological profile was assessed by receptor binding assays at human muscarinic M-1-M-5 receptors stably expressed in CHO cells and by functional studies performed on classical isolated organ preparations, namely, rabbit electrically stimulated vas deferens, and guinea pig electrically stimulated left atrium, ileum, and lung strips. The results showed that the simultaneous presence of one methyl group in both positions 5 and 6 with a trans stereochemical relationship with each other (diastereomers 4 and 5) or the geminal dimethylation in position 6 (compound 8) favour the selective activation of M-3 receptors. Compounds 4, 5, and 8 might be valuable tools in the characterization of the M-3 receptor, as well as provide useful information for the design and development of novel selective M3 antagonists. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.027
• 作为产物：
  描述：

  2-氯-1,1-二甲氧基丙烷 、 甘油 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以75%的产率得到[2-(1-chloroethyl)-[1,3]dioxolan-4-yl]methanol
  参考文献：
  名称：

  Properly substituted 1,4-dioxane nucleus favours the selective M3 muscarinic receptor activation

  摘要：

  Novel analogues of cis-N,N,N-trimethyl-(6-methyl-1,4-dioxan-2-yl)methanaminium iodide (2a) were synthesized by inserting methyl groups alternatively or simultaneously in positions 5 and 6 of the 1,4-dioxane nucleus in all combinations. Their biological profile was assessed by receptor binding assays at human muscarinic M-1-M-5 receptors stably expressed in CHO cells and by functional studies performed on classical isolated organ preparations, namely, rabbit electrically stimulated vas deferens, and guinea pig electrically stimulated left atrium, ileum, and lung strips. The results showed that the simultaneous presence of one methyl group in both positions 5 and 6 with a trans stereochemical relationship with each other (diastereomers 4 and 5) or the geminal dimethylation in position 6 (compound 8) favour the selective activation of M-3 receptors. Compounds 4, 5, and 8 might be valuable tools in the characterization of the M-3 receptor, as well as provide useful information for the design and development of novel selective M3 antagonists. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.027

文献信息

• Properly substituted 1,4-dioxane nucleus favours the selective M3 muscarinic receptor activation
  作者：Alessandro Piergentili、Wilma Quaglia、Fabio Del Bello、Mario Giannella、Maria Pigini、Elisabetta Barocelli、Simona Bertoni、Rosanna Matucci、Marta Nesi、Bruno Bruni

  DOI：10.1016/j.bmc.2009.10.027

  日期：2009.12.15

  Novel analogues of cis-N,N,N-trimethyl-(6-methyl-1,4-dioxan-2-yl)methanaminium iodide (2a) were synthesized by inserting methyl groups alternatively or simultaneously in positions 5 and 6 of the 1,4-dioxane nucleus in all combinations. Their biological profile was assessed by receptor binding assays at human muscarinic M-1-M-5 receptors stably expressed in CHO cells and by functional studies performed on classical isolated organ preparations, namely, rabbit electrically stimulated vas deferens, and guinea pig electrically stimulated left atrium, ileum, and lung strips. The results showed that the simultaneous presence of one methyl group in both positions 5 and 6 with a trans stereochemical relationship with each other (diastereomers 4 and 5) or the geminal dimethylation in position 6 (compound 8) favour the selective activation of M-3 receptors. Compounds 4, 5, and 8 might be valuable tools in the characterization of the M-3 receptor, as well as provide useful information for the design and development of novel selective M3 antagonists. (C) 2009 Elsevier Ltd. All rights reserved.