2-(1H-pyrrol-1-yl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile | 26176-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(1H-pyrrol-1-yl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile
• 英文别名: 2-pyrrol-1-yl-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carbonitrile；2-(1H-pyrrol-1-yl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile；2-pyrrol-1-yl-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile
• CAS: 26176-18-1
• 化学式: C₁₃H₁₂N₂S
• mdl: MFCD00278545
• 分子量: 228.318
• InChiKey: ILTJBWKQAIWNLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(1H-pyrrol-1-yl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile 在 盐酸羟胺 、 caesium carbonate 作用下， 以 乙二醇二甲醚 、 正丁醇 为溶剂， 反应 0.45h， 生成
  参考文献：
  名称：

  Design, synthesis, and cytotoxicity screening of 5-aryl-3-(2-(pyrrolyl) thiophenyl)-1, 2, 4-oxadiazoles as potential antitumor molecules on breast cancer MCF-7 cells

  摘要：

  The work representing the design and the cytotoxic screening of synthetic small molecules (SSMs) such as carbonitriles 3a-c, carboximidamides 4a-c, and oxadiazoles 5-19 as antitumor molecules. Molecules 4c, 9, 12, and 14 show promising cytotoxicity profiles against two cell lines higher than prodigiosin (PG). The results of topoisomerase enzyme inhibition assay show that compounds 4c and 14 display potent inhibitory activity in nano-molar concentration. In addition, DNA-flow cytometry and annexin V analysis also display that compounds 4c, 9, 12, and 14 exhibit antiproliferative activities over MCF-7 cells by cell cycle arrest at G1 phase and apoptosis-inducing activity by increasing cell percentages at pre G1 phase. Moreover, Elisa measurement of p53 and apoptosis mediators, show that carboximidamide 4c and oxadiazoles 9, 12, and 14 significantly up-regulate p53 and cell death mediators as puma and Bax/Bcl-2 ratio levels. Subsequently, pro-apoptotic activities are confirmed by active caspase 3/7 percentages green fluorescence

  DOI：

  10.1016/j.bioorg.2019.01.067
• 作为产物：
  描述：

  环己酮 在 吗啉 、 sulfur 、 溶剂黄146 作用下， 以 正丁醇 为溶剂， 反应 0.5h， 生成 2-(1H-pyrrol-1-yl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile
  参考文献：
  名称：

  Design, Synthesis, and Screening of 5-Aryl-3-(2-(pyrrolyl)thiophenyl)-1,2,4-oxadiazoles as Potential Antitumor Molecules on Breast Cancer MCF-7 Cell Line

  摘要：

  报告的工作涉及合成小分子（碳腈3a-c、羧基咪唑胺4a-c和噁二唑5-19）作为抗肿瘤分子的设计和细胞毒性筛选。分子4c、9、12和14对两种细胞系的细胞毒性特征优于灵菌红素（PG）。拓扑异构酶抑制试验结果显示，羧基咪唑胺4c和噁二唑14在纳摩尔浓度下表现出比PG更强的抑制活性。此外，羧基咪唑胺4c和噁二唑9、12、和14通过DNA流式细胞术和 annexin V 分析显示，在G1期阻滞细胞周期并诱导凋亡活性，通过增加pre G1和G2/M期的细胞比例。此外，对p53和细胞死亡介质的测量表明，羧基咪唑胺4c和噁二唑9、12、和14显著上调p53、Puma和Bax/Bcl-2比率水平。随后的绿色荧光活性caspase 3/7百分比测定证实了促凋亡活性。

  DOI：

  10.1248/cpb.c18-00636

文献信息

• Design, Synthesis, and Screening of 5-Aryl-3-(2-(pyrrolyl)thiophenyl)-1,2,4-oxadiazoles as Potential Antitumor Molecules on Breast Cancer MCF-7 Cell Line
  作者：Mohammed K. Abd el hameid

  DOI：10.1248/cpb.c18-00636

  日期：2018.12.1

  The work reported the design and cytotoxic screening of synthetic small molecules: carbonitriles 3a–c, carboximidamides 4a–c, and oxadiazoles 5–19 as antitumor molecules. Molecules 4c, 9, 12, and 14 show promising cytotoxicity profiles against two cell lines higher than prodigiosin (PG). The results of topoisomerase enzyme inhibition assay show that carboximidamide 4c and oxadiazole 14 display potent inhibitory activity in nano-molar concentration higher than PG. In addition, carboximidamide 4c and oxadiazoles 9, 12, and 14 exhibit antiproliferative activities over MCF-7 cells by cell cycle arrest at G1 phase and apoptosis inducing activity by increasing cell population percentages at pre G1 and G2/M phases as shown by DNA-flow cytometry assay and annexin V analysis. Moreover, measurement of p53 and cell death mediators, show that carboximidamide 4c and oxadiazoles 9, 12, and 14 significantly up-regulate p53, Puma and Bax/Bcl-2 ratio levels. Subsequently, pro-apoptotic activities are confirmed by active caspase 3/7 percentages green fluorescence assay.

  报告的工作涉及合成小分子（碳腈3a-c、羧基咪唑胺4a-c和噁二唑5-19）作为抗肿瘤分子的设计和细胞毒性筛选。分子4c、9、12和14对两种细胞系的细胞毒性特征优于灵菌红素（PG）。拓扑异构酶抑制试验结果显示，羧基咪唑胺4c和噁二唑14在纳摩尔浓度下表现出比PG更强的抑制活性。此外，羧基咪唑胺4c和噁二唑9、12、和14通过DNA流式细胞术和 annexin V 分析显示，在G1期阻滞细胞周期并诱导凋亡活性，通过增加pre G1和G2/M期的细胞比例。此外，对p53和细胞死亡介质的测量表明，羧基咪唑胺4c和噁二唑9、12、和14显著上调p53、Puma和Bax/Bcl-2比率水平。随后的绿色荧光活性caspase 3/7百分比测定证实了促凋亡活性。
• Design, synthesis, and cytotoxicity screening of 5-aryl-3-(2-(pyrrolyl) thiophenyl)-1, 2, 4-oxadiazoles as potential antitumor molecules on breast cancer MCF-7 cells
  作者：Mohammed K. Abd el hameid、Manal R. Mohammed

  DOI：10.1016/j.bioorg.2019.01.067

  日期：2019.5

  The work representing the design and the cytotoxic screening of synthetic small molecules (SSMs) such as carbonitriles 3a-c, carboximidamides 4a-c, and oxadiazoles 5-19 as antitumor molecules. Molecules 4c, 9, 12, and 14 show promising cytotoxicity profiles against two cell lines higher than prodigiosin (PG). The results of topoisomerase enzyme inhibition assay show that compounds 4c and 14 display potent inhibitory activity in nano-molar concentration. In addition, DNA-flow cytometry and annexin V analysis also display that compounds 4c, 9, 12, and 14 exhibit antiproliferative activities over MCF-7 cells by cell cycle arrest at G1 phase and apoptosis-inducing activity by increasing cell percentages at pre G1 phase. Moreover, Elisa measurement of p53 and apoptosis mediators, show that carboximidamide 4c and oxadiazoles 9, 12, and 14 significantly up-regulate p53 and cell death mediators as puma and Bax/Bcl-2 ratio levels. Subsequently, pro-apoptotic activities are confirmed by active caspase 3/7 percentages green fluorescence