8-[3-(trifluoromethyl)phenyl]-4H-[1,2,4]oxadiazolo[3,4-c][1,4]benzoxazin-1-one | 1219717-31-3

• 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: 8-[3-(trifluoromethyl)phenyl]-4H-[1,2,4]oxadiazolo[3,4-c][1,4]benzoxazin-1-one
• CAS: 1219717-31-3
• 化学式: C₁₆H₉F₃N₂O₃
• 分子量: 334.254
• InChiKey: ONFFPJSVOQJKBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-[3-(trifluoromethyl)phenyl]-2H-1,4-benzoxazin-3(4H)-one oxime 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 反应 24.0h， 以69%的产率得到8-[3-(trifluoromethyl)phenyl]-4H-[1,2,4]oxadiazolo[3,4-c][1,4]benzoxazin-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of oxadiazole derivatives as inhibitors of soluble guanylyl cyclase

  摘要：

  Soluble guanylyl cyclase (sGC) is an ubiquitously expressed enzyme that generates the second messenger cGMP and hence, leads to a number of physiological responses including vasodilation, inhibition of platelet aggregation and neurotransmission. Whilst many activating and stimulating modulators of sGC were identified and studied in recent years, only two selective inhibitors are known: ODQ and NS 2028. Furthermore, a synthetic approach to these inhibitors has not been reported yet. Herein, we describe a novel and efficient synthesis of these inhibitors, as well as the preparation of three different classes of NS 2028 analogues. Biological evaluation of this library using rat aortic smooth muscle cells revealed four new compounds with good to moderate sGC inhibitory activity. Our experiments underline the major importance of the oxadiazole ring in ODQ and NS 2028 for the efficiency of this class of inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.027

文献信息

• Synthesis and biological evaluation of oxadiazole derivatives as inhibitors of soluble guanylyl cyclase
  作者：Margarete von Wantoch Rekowski、Anastasia Pyriochou、Nektarios Papapetropoulos、Anne Stößel、Andreas Papapetropoulos、Athanassios Giannis

  DOI：10.1016/j.bmc.2009.12.027

  日期：2010.2

  Soluble guanylyl cyclase (sGC) is an ubiquitously expressed enzyme that generates the second messenger cGMP and hence, leads to a number of physiological responses including vasodilation, inhibition of platelet aggregation and neurotransmission. Whilst many activating and stimulating modulators of sGC were identified and studied in recent years, only two selective inhibitors are known: ODQ and NS 2028. Furthermore, a synthetic approach to these inhibitors has not been reported yet. Herein, we describe a novel and efficient synthesis of these inhibitors, as well as the preparation of three different classes of NS 2028 analogues. Biological evaluation of this library using rat aortic smooth muscle cells revealed four new compounds with good to moderate sGC inhibitory activity. Our experiments underline the major importance of the oxadiazole ring in ODQ and NS 2028 for the efficiency of this class of inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.