6-ethynyl-4-morpholinobenzo[c][1,2,5]oxadiazole | 1284231-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 6-ethynyl-4-morpholinobenzo[c][1,2,5]oxadiazole
• 英文别名: 6-Ethynyl-4-(morpholin-4-yl)-2,1,3-benzoxadiazole；6-ethynyl-4-morpholin-4-yl-2,1,3-benzoxadiazole
• CAS: 1284231-75-9
• 化学式: C₁₂H₁₁N₃O₂
• mdl: MFCD25976098
• 分子量: 229.238
• InChiKey: SWVZCRNKUNBPLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-ethynyl-4-morpholinobenzo[c][1,2,5]oxadiazole 、 5-碘-2'-脱氧胞苷 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 生成 5-(2-(4-ethynyl-6-morpholinobenzo[c][1,2,5]oxadiazolyl))-2'-deoxycytidine
  参考文献：
  名称：

  Novel Fluorescent Pyrimidine Nucleosides Containing 2,1,3-Benzoxadiazole and Naphtho-[1,2,3-CD] Indole-6 (2H)-One Fragments

  摘要：

  A series of novel fluorescent pyrimidine nucleosides containing 2,1,3-benzoxadiazole or naphtho[1,2,3-cd]indole-6 (2h)-one fragments was designed and synthesized. Introduction of fluorescent fragments into the position 5 of the uridine or cytidine heterocycle was carried out in two ways: by Sonogashira Coupling Reaction and CuI-catalyzed cycloaddition ("click" reaction). The obtained nucleoside derivatives became fluorescent due to the inserted fragments. The excitation wavelength (440-450 nm) was outside the absorption band of many biomolecules and significantly differed from the emission wavelength (560-600 nm). In addition, the intended nucleoside analogs were shown to kill cultured human tumor cells at submicromolar concentrations.

  DOI：

  10.1080/15257770.2014.913064
• 作为产物：
  描述：

  2-methyl-4-(7-morpholino-2,1,3-benzoxadiazol-5-yl)but-3-yn-2-ol 在 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以80%的产率得到6-ethynyl-4-morpholinobenzo[c][1,2,5]oxadiazole
  参考文献：
  名称：

  N-烷基-6（4）-溴-2,1,3-苯并恶二唑-4（6）-胺与末端炔烃的反应

  摘要：

  N-烷基-6（4）-溴-2,1,3-苯并恶二唑-4（6）-胺与末端炔烃反应，得到氨基取代的2,1,3-苯并恶二唑，其含有直接连接至碳环的炔属片段。

  DOI：

  10.1134/s1070428012010228

文献信息

• Reaction of N-Alkyl-6(4)-bromo-2,1,3-benzoxadiazol-4(6)-amines with terminal alkynes
  作者：L. M. Gornostaev、A. S. Kuznetsova、N. V. Geets、E. A. Bocharova

  DOI：10.1134/s1070428012010228

  日期：2012.1

  N-Alkyl-6(4)-bromo-2,1,3-benzoxadiazol-4(6)-amines reacted with terminal alkynes to give aminosubstituted 2,1,3-benzoxadiazoles containing acetylenic fragments directly attached to the carbocycle.

  N-烷基-6（4）-溴-2,1,3-苯并恶二唑-4（6）-胺与末端炔烃反应，得到氨基取代的2,1,3-苯并恶二唑，其含有直接连接至碳环的炔属片段。
• Novel Fluorescent Pyrimidine Nucleosides Containing 2,1,3-Benzoxadiazole and Naphtho-[1,2,3-CD] Indole-6 (2H)-One Fragments
  作者：Svetlana V. Vasilyeva、Anastasya S. Kuznetsova、Juliya G. Khalyavina、Valeria A. Glazunova、Alexander A. Shtil、Leonid M. Gornostaev、Vladimir N. Silnikov

  DOI：10.1080/15257770.2014.913064

  日期：2014.9.2

  A series of novel fluorescent pyrimidine nucleosides containing 2,1,3-benzoxadiazole or naphtho[1,2,3-cd]indole-6 (2h)-one fragments was designed and synthesized. Introduction of fluorescent fragments into the position 5 of the uridine or cytidine heterocycle was carried out in two ways: by Sonogashira Coupling Reaction and CuI-catalyzed cycloaddition ("click" reaction). The obtained nucleoside derivatives became fluorescent due to the inserted fragments. The excitation wavelength (440-450 nm) was outside the absorption band of many biomolecules and significantly differed from the emission wavelength (560-600 nm). In addition, the intended nucleoside analogs were shown to kill cultured human tumor cells at submicromolar concentrations.