双[(炔丙氧基)甲基]醚 | 139758-75-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 双[(炔丙氧基)甲基]醚
• 英文名称: bis<(propargyloxy)methyl> ether
• 英文别名: 3-(Prop-2-ynoxymethoxymethoxy)prop-1-yne
• CAS: 139758-75-1
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: KBLHZLUIVAGQBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 2-丙炔-1-醇 在 盐酸 作用下， 以 水 为溶剂， 反应 0.75h， 以60%的产率得到3-chloromethoxy-propyne
  参考文献：
  名称：

  Synthesis and biological studies of unsaturated acyclonucleoside analogs of S-adenosyl-L-homocysteine hydrolase inhibitors

  摘要：

  The design, synthesis, and biological evaluation of several unsaturated acyclonucleosides related to augustmycin A are described. The (propargyloxy)methyl acyclonucleoside analogues of 6-chloropurine, adenine, 6-methoxypurine, hypoxanthine, 6-mercaptopurine, and azathioprine have been prepared. The 9-[(propargyloxy)methyl]adenine (5) and 9-[(propargyloxy)methyl]hypoxanthine (12) analogues were converted to the corresponding 5'-tributylstannyl intermediates (9 and 13), respectively, which gave 9-[[[(Z)-5-iodo-5-propenyl]oxy]methyl]adenine (10) and 9-[[[(Z)-5-iodo-5-propenyl]oxy]methyl]hypoxanthine (14), respectively, after iododestannylation. The [I-125]-radiolabeled congeners of 10 and 14 were prepared as potential metabolic markers. Among the unsaturated acyclonucleosides tested, 9-[(propargyloxy)methyl]-6-chloropurine (3), 9-[(propargyloxy)methyl]-6-mercaptopurine (15), 9-[(proparglyoxy)methyl]azathioprine (17), and angustmycin A analogue 10 showed inhibition of cancer cell growth, but only at a minimal level, and 17 also showed 14% cancer cel death in vitro. Compound 10 provided approximately 50% protection against HIV at 10(-4) M concentrations. Biodistribution results of [I-125]-10 in mice indicate that compound 10 is readily metabolized via deiodination in vivo, possibly by serving as a substrate for the enzyme S-adenosyl-L-homocysteine hydrolase.

  DOI：

  10.1021/jm00086a012