6-<2-(trimethylsilyl)ethynyl>-3,4-dihydroquinolin-2(1H)-one | 138260-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-<2-(trimethylsilyl)ethynyl>-3,4-dihydroquinolin-2(1H)-one
• 英文别名: 6-((trimethylsilyl)ethynyl)-3,4-dihydro-1H-quinolin-2-one；6-(2-trimethylsilylethynyl)-3,4-dihydro-1H-quinolin-2-one
• CAS: 138260-91-0
• 化学式: C₁₄H₁₇NOSi
• 分子量: 243.381
• InChiKey: WXNZIOHMKIEEFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-<2-(trimethylsilyl)ethynyl>-3,4-dihydroquinolin-2(1H)-one 在 劳森试剂 、 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 溶剂黄146 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 反应 35.33h， 生成 2’-deoxy-5-(2-(diphenylmethylene)-7-ethynyl-4,5-dihydroimidazo[1,2-a]quinolin-1(2H)-one)cytidine
  参考文献：
  名称：

  4-（二芳基亚甲基）咪唑啉酮共轭荧光核酸的合成与性质

  摘要：

  一种新颖的荧光胞苷衍生物（DC DAIN）轴承4-（二芳）咪唑啉酮类（DAINs）在C5位上成功地合成并掺入寡核苷酸。带有dC DAIN的寡核苷酸与互补链以序列特异性方式杂交，并且荧光强度根据双链DNA或RNA中与dC DAIN相反的核碱基而改变。有趣的是，当含dC DAIN的寡核苷酸与错配序列杂交时，荧光强度更高。特别是当dC DAIN 荧光强度位于无碱基位置的相反位置，荧光强度是单链状态下的四倍。

  DOI：

  10.1016/j.tetlet.2016.06.012
• 作为产物：
  描述：

  3,4-二氢-2(1H)-喹啉酮 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 作用下， 以 吡啶 、 三乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.25h， 生成 6-<2-(trimethylsilyl)ethynyl>-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  3,4-Dihydroquinolin-2(1H)-ones as combined inhibitors of thromboxane A2 synthase and cAMP phosphodiesterase

  摘要：

  A series of 1H-imidazol-1-yl- and 3-pyridyl-substituted 3,4-dihydroquinolin-2(1H)-ones was designed and synthesized as combined inhibitors of thromboxane (TXA2) synthase and cAMP phosphodiesterase (PDE) in human blood platelets. A number of structures, e.g. 4b, 7a, 7e, 13a, and 21-25, were superior to dazoxiben 26 as inhibitors of TXA2 synthase in in vitro ADP-induced aggregation experiments with human blood platelets. The TXA2 synthase inhibitory activity was confirmed by measurement of the prostanoid metabolites derived from C-14-labeled arachidonic acid. Three compounds (7a, 7e, and 25) demonstrated in vitro inhibition of human platelet cAMP PDE at micromolar concentrations in conjunction with their TXA2 synthase inhibitory activity. Synergistic enhancement of antiaggregatory and antithrombotic actions was expected when simultaneous stimulation of adenylate cyclase (through increased PGI2 production) and inhibition of platelet cAMP PDE were possible from the same compound. Ex vivo and in vivo experiments were conducted in rats and mice, respectively, to evaluate the effects of compounds 7e and 23 on platelet aggregation and thrombotic events within these animals. Compound 7e, which has a comparable level of TXA2 synthase (IC50 1.2-mu-M) and human platelet cAMP PDE (IC50 6.4-mu-M) inhibitory activities, was found to be orally bioavailable with a long duration of action and offered effective protection against mortality in a collagen-epinephrine-induced pulmonary thromboembolism model in mice. Significant blood pressure and heart rate effects were observed for several compounds, e.g. 7e, 9e, 13a, 13d, 18, 20, 21, and 23, when dosed orally in conscious spontaneously hypertensive rats.

  DOI：

  10.1021/jm00082a002