5-ethynyl-2-(2-(4-(thiophen-2-yl)benzylidene)hydrazinyl)pyridine | 1293385-68-8

• 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: 5-ethynyl-2-(2-(4-(thiophen-2-yl)benzylidene)hydrazinyl)pyridine
• CAS: 1293385-68-8
• 化学式: C₁₈H₁₃N₃S
• 分子量: 303.387
• InChiKey: UNTYPJSQFPZEHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.51
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-ethynyl-2-(2-(4-(thiophen-2-yl)benzylidene)hydrazinyl)pyridine 在 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以83%的产率得到6-ethynyl-3,3-difluoro-2-(4-(thiophen-2-yl)benzylidene)-2,3-dihydro[1,2,4,3]triazaborolo[4,5-a]pyridin-2-ium-3-uide
  参考文献：
  名称：

  Design and Synthesis of a New Class of Membrane-Permeable Triazaborolopyridinium Fluorescent Probes

  摘要：

  A new class of fluorescent triazaborolopyridinium compounds was synthesized from hydrazones of 2-hydrazinylpyridine (HPY) and evaluated as potential dyes for live-cell imaging applications. The HPY dyes are small, their absorption/emission properties are tunable through variation of pyridyl or hydrazone substituents, and they offer favorable photophysical characteristics featuring large Stokes shifts and general insensitivity to solvent or pH. The stability, neutral charge, cell membrane permeability, and favorable relative influences on the water solubility of HPY conjugates are complementary to existing fluorescent dyes and offer advantages for the development of receptor-targeted small-molecule probes. This potential was assessed through the development of a new class of cysteine-derived HPY-conjugate imaging agents for the kinesin spindle protein (KSP) that is expressed in the cytoplasm during mitosis and is a promising chemotherapeutic target. Conjugates possessing the neutral HPY or charged Alexa Fluor dyes that function as potent, selective allosteric inhibitors of the KSP motor were compared using biochemical and cell-based phenotypic assays and live-cell imaging. These results demonstrate the effectiveness of the HPY dye moiety as a component of probes for an intracellular protein target and highlight the importance of dye structure in determining the pathway of cell entry and the overall performance of small-molecule conjugates as imaging agents.

  DOI：

  10.1021/ja2005175
• 作为产物：
  描述：

  2-氯-5-乙炔吡啶 在 吡啶 、 肼 作用下， 反应 20.0h， 生成 5-ethynyl-2-(2-(4-(thiophen-2-yl)benzylidene)hydrazinyl)pyridine
  参考文献：
  名称：

  Design and Synthesis of a New Class of Membrane-Permeable Triazaborolopyridinium Fluorescent Probes

  摘要：

  A new class of fluorescent triazaborolopyridinium compounds was synthesized from hydrazones of 2-hydrazinylpyridine (HPY) and evaluated as potential dyes for live-cell imaging applications. The HPY dyes are small, their absorption/emission properties are tunable through variation of pyridyl or hydrazone substituents, and they offer favorable photophysical characteristics featuring large Stokes shifts and general insensitivity to solvent or pH. The stability, neutral charge, cell membrane permeability, and favorable relative influences on the water solubility of HPY conjugates are complementary to existing fluorescent dyes and offer advantages for the development of receptor-targeted small-molecule probes. This potential was assessed through the development of a new class of cysteine-derived HPY-conjugate imaging agents for the kinesin spindle protein (KSP) that is expressed in the cytoplasm during mitosis and is a promising chemotherapeutic target. Conjugates possessing the neutral HPY or charged Alexa Fluor dyes that function as potent, selective allosteric inhibitors of the KSP motor were compared using biochemical and cell-based phenotypic assays and live-cell imaging. These results demonstrate the effectiveness of the HPY dye moiety as a component of probes for an intracellular protein target and highlight the importance of dye structure in determining the pathway of cell entry and the overall performance of small-molecule conjugates as imaging agents.

  DOI：

  10.1021/ja2005175