3-(2-(prop-2-ynyloxy)ethyl)-2H-benzo[e][1,3]oxazin-4(3H)-one | 1567841-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-(2-(prop-2-ynyloxy)ethyl)-2H-benzo[e][1,3]oxazin-4(3H)-one
• CAS: 1567841-72-8
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: LMNAIGGFBXLUPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(2-iodo-4-nitrophenyl)methanesulfonamide 、 3-(2-(prop-2-ynyloxy)ethyl)-2H-benzo[e][1,3]oxazin-4(3H)-one 在 copper(l) iodide 、 palladium 10% on activated carbon 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以61%的产率得到3-(2-((1-(methylsulfonyl)-5-nitro-1H-indol-2-yl)methoxy)ethyl)-2H-benzo[e][1,3]oxazin-4(3H)-one
  参考文献：
  名称：

  Synthesis of 2H- 1,3-benzoxazin-4(3 H )-one derivatives containing indole moiety: Their in vitro evaluation against PDE4B

  摘要：

  A number of 2H-1,3-benzoxazin-4(3H)-one derivatives containing indole or benzofuran moieties were synthesized by using Pd/C-Cu mediated coupling-cyclization strategy as a key step. The o-iodoanilides or o-iodophenol were coupled with 3-{2-(prop-2-ynyloxy) ethyl}-2H-benzo[e][1,3] oxazin-4(3H)-one using 10% Pd/C-CuI-PPh3 as a catalyst system and Et3N as a base to give the target compounds. All the synthesized compounds were tested for their PDE4B inhibitory potential in vitro using a cell based cAMP reporter assay. Some of them showed fold increase of the cAMP level when tested at 30 lM. A representative compound showed encouraging PDE4B inhibitory properties that were supported by its docking results. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.117
• 作为产物：
  描述：

  水杨酸甲酯 在 盐酸 、 sodium hydride 、 溶剂黄146 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(2-(prop-2-ynyloxy)ethyl)-2H-benzo[e][1,3]oxazin-4(3H)-one
  参考文献：
  名称：

  Synthesis of 2H- 1,3-benzoxazin-4(3 H )-one derivatives containing indole moiety: Their in vitro evaluation against PDE4B

  摘要：

  A number of 2H-1,3-benzoxazin-4(3H)-one derivatives containing indole or benzofuran moieties were synthesized by using Pd/C-Cu mediated coupling-cyclization strategy as a key step. The o-iodoanilides or o-iodophenol were coupled with 3-{2-(prop-2-ynyloxy) ethyl}-2H-benzo[e][1,3] oxazin-4(3H)-one using 10% Pd/C-CuI-PPh3 as a catalyst system and Et3N as a base to give the target compounds. All the synthesized compounds were tested for their PDE4B inhibitory potential in vitro using a cell based cAMP reporter assay. Some of them showed fold increase of the cAMP level when tested at 30 lM. A representative compound showed encouraging PDE4B inhibitory properties that were supported by its docking results. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.117