2-(6-(2-thioanisyl)-3(Z)-hexene-1,5-diynyl)aniline

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(6-(2-thioanisyl)-3(Z)-hexene-1,5-diynyl)aniline
• 英文别名: 2-(6-(2-methylthiophenyl)-3(Z)-hexen-1,5-diynyl)aniline；2-[(Z)-6-(2-methylsulfanylphenyl)hex-3-en-1,5-diynyl]aniline
• 化学式: C₁₉H₁₅NS
• 分子量: 289.401
• InChiKey: ABGMGRWKYRXUSZ-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(6-(2-thioanisyl)-3(Z)-hexene-1,5-diynyl)aniline 、 5-溴戊酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到5-bromo-N-(2-((Z)-6-(2-(methylthio)phenyl)hexa-3-en-1,5-diynyl)phenyl)pentanamide
  参考文献：
  名称：

  1-（2-（（Z）-6-（2-（三氟甲基）苯基）六-3-en-1,5-二炔基）苯基）哌啶-2-一作为新型有效的凋亡剂

  摘要：

  化合物4a – f，5a – f和6 – 9对人类肿瘤细胞系显示出显着的生长抑制活性。在这些化合物中，1-（2-（（Z）-6-（2-（三氟甲基）苯基）六-3-en-1,5-二炔基）苯基）哌啶-2-酮（8）显示出最有效的生长抑制活性。化合物8也将癌细胞阻滞在G2 / M期，并通过激活caspase-3和-9诱导细胞凋亡。根据蛋白质印迹分析，化合物8可以上调Bax，下调Bcl-2和XIAP，并促进细胞色素c的释放。

  DOI：

  10.1016/j.bmc.2009.09.042
• 作为产物：
  描述：

  2-[(三甲基甲硅烷基)乙炔基]苯胺 在 四(三苯基膦)钯 copper(l) iodide 、 potassium carbonate 、 正丁胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 12.0h， 生成 2-(6-(2-thioanisyl)-3(Z)-hexene-1,5-diynyl)aniline
  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

• 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.
• 1-(2-((Z)-6-(2-(Trifluoromethyl)phenyl)hexa-3-en-1,5-diynyl)phenyl)piperidin-2-one as a new potent apoptosis agent
  作者：Yu-Sheng Tu、Tsai-Hui Duh、Chen-Yi Tseng、Ying-Ting Lin、Yu-Hsiang Lo、Yi-Ling Hu、Chen-Hung Chen、Ching-Ming Chien、Sheng-Huei Yang、Shinne-Ren Lin、Shyh-Chyun Yang、Ming-Jung Wu

  DOI：10.1016/j.bmc.2009.09.042

  日期：2009.11

  Compounds 4a–f, 5a–f and 6–9, showed significant growth inhibition activity against human tumor cell lines. Of these compounds, 1-(2-((Z)-6-(2-(trifluoromethyl)phenyl)hexa-3-en-1,5-diynyl)phenyl)piperidin-2-one (8) displayed the most potent growth inhibition activity. Compound 8 also arrested cancer cells in G2/M phase and induced apoptosis via activation of caspase-3 and -9. According to western-blotting

  化合物4a – f，5a – f和6 – 9对人类肿瘤细胞系显示出显着的生长抑制活性。在这些化合物中，1-（2-（（Z）-6-（2-（三氟甲基）苯基）六-3-en-1,5-二炔基）苯基）哌啶-2-酮（8）显示出最有效的生长抑制活性。化合物8也将癌细胞阻滞在G2 / M期，并通过激活caspase-3和-9诱导细胞凋亡。根据蛋白质印迹分析，化合物8可以上调Bax，下调Bcl-2和XIAP，并促进细胞色素c的释放。