1,6-di(2-pyridinyl)-3(Z)-hexene-1,5-diyne

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1,6-di(2-pyridinyl)-3(Z)-hexene-1,5-diyne
• 英文别名: (Z)-1,6-bis(pyridin-2-yl)hexa-3-en-1,5-diyne；2-[(Z)-6-pyridin-2-ylhex-3-en-1,5-diynyl]pyridine
• 化学式: C₁₆H₁₀N₂
• 分子量: 230.269
• InChiKey: LZWZFDBHUPCQIM-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,6-di(2-pyridinyl)-3(Z)-hexene-1,5-diyne 、 silver tetrafluoroborate 以 二氯甲烷-D2 为溶剂， 生成 [(Z)-1,6-bis(pyridin-2-yl)hexa-3-en-1,5-diyne silver(I)]⁺ tetrafluoroborate
  参考文献：
  名称：

  用卤素键、配位键和氢键调节光开关性能：相对键强度的比较

  摘要：

  烯二炔光开关的行为受卤素键、配位键和氢键的调节。通过核磁共振和计算研究，我们证明二级键的相对强度直接影响光异构化速率和光稳态。

  DOI：

  10.1039/d1cc01827b
• 作为产物：
  描述：

  2-碘吡啶 、 1,6-bis(trimethylsilyl)-3(Z)-hexene-1,5-diyne 在 四(三苯基膦)钯 copper(l) iodide 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以35%的产率得到1,6-di(2-pyridinyl)-3(Z)-hexene-1,5-diyne
  参考文献：
  名称：

  Cytotoxicities, cell cycle and caspase evaluations of 1,6-diaryl-3(Z)-hexen-1,5-diynes, 2-(6-aryl-3(Z)-hexen-1,5-diynyl)anilines and their derivatives

  摘要：

  Compounds 3, 6-7, 9-10, 15-17, and 20-21 showed growth inhibition effects on a full panel of 60 human cancer cell lines, and most of the average IC50 values of the indicated analogues were from < 0.01 to 96.6 mu M, in which analogues 16 and 17 revealed the highest cytotoxic activity with the cancer cell lines at 10(-7) M concentration range. During the cell cycle analysis, a moderate to high apoptotic progress induction was shown by 3, 9, 16-17, and 20 compared with the control, which 2-(6-(2-thienyl)-3(Z)-hexen-1,5-diynyl)aniline 16 showed the highest apoptotic effect. Structures 16-17 displayed a significant G2/M phase arrest in the cell growth cycle compared with other derivatives, which the proportions of the G2/M phase cells were accumulated to 71.5% and 82.6%, respectively. Moreover, the colorimetric assay of 16-17 also provided advanced evidence to the relationship between the compounds and the caspase-3 enzyme, which was one of the major promoters of apoptotic effect. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.062