1,4-di(selenophen-2-yl)butane-1,4-dione | 200509-14-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-di(selenophen-2-yl)butane-1,4-dione
• 英文别名: 1,4-di(selenophen-2-yl)-1,4-butanedione
• CAS: 200509-14-4
• 化学式: C₁₂H₁₀O₂Se₂
• 分子量: 344.13
• InChiKey: GPPAICVQUDRZAI-UHFFFAOYSA-N

物化性质

• 沸点：
  459.1±30.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  正己胺 、 1,4-di(selenophen-2-yl)butane-1,4-dione 在 丙酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以61%的产率得到1-hexyl-2,5-di(selenophen-2-yl)-1H-pyrrole
  参考文献：
  名称：

  Facile synthesis and characterization of new polymerizable conjugated 2,5-di(selenophen-2-yl)pyrroles and 2,5-difuranylpyrroles

  摘要：

  A facile synthesis of novel pi-conjugated 2,5-di(selenophen-2-yl)pyrroles (SeNSe) and 2,5-difuranylpyrroles (ONO) via Paal-Knorr reaction as the key step is presented. Photophysical and electrochemical studies of the various products have been explored. A bathochromic shift of the emission maximum is observed for all SeNSes over ONOs. Extended conjugation with a phenyl moiety further promotes the bathochromic shift. These SeNSe and ONO derivatives exhibit lower oxidation potentials than their terselenophene and terthiophene analogues. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.12.019
• 作为产物：
  描述：

  硒酚 、 丁二酰氯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 以25%的产率得到1,4-di(selenophen-2-yl)butane-1,4-dione
  参考文献：
  名称：

  1,4-Diselenophene-1,4-diketone Triggers Caspase-Dependent Apoptosis in Human Melanoma A375 Cells through Induction of Mitochondrial Dysfunction

  摘要：

  流行病学、临床前和临床研究都支持硒化合物作为潜在的癌症化学预防和化疗药物。本研究通过双弗里德尔-卡夫斯反应合成了一种新型硒基化合物--1,4-二硒吩-1,4-二酮（DSeD）。尽管具有这种效力，但 DSeD 对人类正常细胞、HS68 成纤维细胞和 HK-2 肾细胞相对无毒。这些结果表明，DSeD 在癌细胞和正常细胞之间具有很强的选择性。DSeD 对人类黑色素瘤 A375 细胞的凋亡诱导作用表现为亚 G1 细胞群的积累、DNA 断裂和核凝缩。Caspase-9 的激活和线粒体膜电位的耗竭表明线粒体介导的凋亡途径已经启动。用一般的caspase抑制剂z-VAD-fmk和caspase-9抑制剂z-LEHD-fmk预处理细胞可明显抑制细胞凋亡，这表明caspase和线粒体在DSeD诱导的细胞凋亡中起着重要作用。此外，DSeD诱导的细胞凋亡与活性氧的生成无关。综上所述，我们的研究结果表明，DSeD通过激活线粒体介导的细胞凋亡途径诱导A375细胞发生依赖于caspase的细胞凋亡。

  DOI：

  10.1248/cpb.59.1227

文献信息

• Facile synthesis and characterization of new polymerizable conjugated 2,5-di(selenophen-2-yl)pyrroles and 2,5-difuranylpyrroles
  作者：Pitchamuthu Amaladass、Kalyan Kumar Pasunooti、Zihuan Png、Xue-Wei Liu

  DOI：10.1016/j.tetlet.2010.12.019

  日期：2011.2

  A facile synthesis of novel pi-conjugated 2,5-di(selenophen-2-yl)pyrroles (SeNSe) and 2,5-difuranylpyrroles (ONO) via Paal-Knorr reaction as the key step is presented. Photophysical and electrochemical studies of the various products have been explored. A bathochromic shift of the emission maximum is observed for all SeNSes over ONOs. Extended conjugation with a phenyl moiety further promotes the bathochromic shift. These SeNSe and ONO derivatives exhibit lower oxidation potentials than their terselenophene and terthiophene analogues. (C) 2010 Elsevier Ltd. All rights reserved.
• 1,4-Diselenophene-1,4-diketone Triggers Caspase-Dependent Apoptosis in Human Melanoma A375 Cells through Induction of Mitochondrial Dysfunction
  作者：Yi Luo、Xiaoling Li、Xiaochun Huang、Yum-Shing Wong、Tianfeng Chen、Yibo Zhang、Wenjie Zheng

  DOI：10.1248/cpb.59.1227

  日期：——

  Epidemiological, preclinical and clinical studies have supported the role of selenocompounds as potential cancer chemopreventive and chemotherapeutic agents. In this study, a novel selenophene-based compound, 1,4-diselenophene-1,4-diketone (DSeD), has been synthesized by Double Friedel–Crafts reaction and identified as a potent antiproliferative agent against a panel of six human caner cell lines. Despite this potency, DSeD was relatively nontoxic toward human normal cells, HS68 fibroblasts and HK-2 kidney cells. These results suggest that DSeD possesses great selectivity between cancer and normal cells. Induction of apoptosis in human melanoma A375 cells by DSeD was evidenced by accumulation of sub-G1 cell population, DNA fragmentation and nuclear condensation. Activation of caspase-9 and depletion of mitochondrial membrane potential indicated the initiation of the mitochondria-mediated apoptosis pathway. Pretreatment of cells with general caspase inhibitor z-VAD-fmk and caspase-9 inhibitor z-LEHD-fmk significantly suppressed the cell apoptosis, demonstrating the important roles of caspase and mitochondria in DSeD-induced apoptotic cell death. Furthermore, DSeD-induced apoptosis was found independent of reactive oxygen species generation. Taken together, our results suggest that DSeD induces caspase-dependent apoptosis in A375 cells through activation of mitochondria-mediated apoptosis pathway.

  流行病学、临床前和临床研究都支持硒化合物作为潜在的癌症化学预防和化疗药物。本研究通过双弗里德尔-卡夫斯反应合成了一种新型硒基化合物--1,4-二硒吩-1,4-二酮（DSeD）。尽管具有这种效力，但 DSeD 对人类正常细胞、HS68 成纤维细胞和 HK-2 肾细胞相对无毒。这些结果表明，DSeD 在癌细胞和正常细胞之间具有很强的选择性。DSeD 对人类黑色素瘤 A375 细胞的凋亡诱导作用表现为亚 G1 细胞群的积累、DNA 断裂和核凝缩。Caspase-9 的激活和线粒体膜电位的耗竭表明线粒体介导的凋亡途径已经启动。用一般的caspase抑制剂z-VAD-fmk和caspase-9抑制剂z-LEHD-fmk预处理细胞可明显抑制细胞凋亡，这表明caspase和线粒体在DSeD诱导的细胞凋亡中起着重要作用。此外，DSeD诱导的细胞凋亡与活性氧的生成无关。综上所述，我们的研究结果表明，DSeD通过激活线粒体介导的细胞凋亡途径诱导A375细胞发生依赖于caspase的细胞凋亡。