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

文献信息

• Modulating photoswitch performance with halogen, coordinative and hydrogen bonding: a comparison of relative bond strengths
  作者：Sofia Lindblad、Daniel Sethio、Orion B. Berryman、Máté Erdélyi

  DOI：10.1039/d1cc01827b

  日期：——

  The behavior of an enediyne photoswitch is modulated with halogen bonding, coordinative bonding and hydrogen bonding. Through NMR and computational studies we demonstrate that the relative strength of the secondary bonding directly influences the rate of photoisomerization and the photostationary state.

  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。
• 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
  作者：Chi-Fong Lin、Yu-Hsiang Lo、Ming-Chu Hsieh、Yi-Hua Chen、Jeh-Jeng Wang、Ming-Jung Wu

  DOI：10.1016/j.bmc.2005.02.062

  日期：2005.5

  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.