(Z)-3-(4-selenocyanatophenylcarbamoyl)acrylic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-(4-selenocyanatophenylcarbamoyl)acrylic acid
• 英文别名: (Z)-4-oxo-4-(4-selenocyanatoanilino)but-2-enoic acid
• 化学式: C₁₁H₈N₂O₃Se
• 分子量: 295.156
• InChiKey: QJDLUDLXQWOCMQ-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3-(4-selenocyanatophenylcarbamoyl)acrylic acid 在 sodium acetate 、 乙酸酐 作用下， 反应 2.0h， 以52%的产率得到1-(4-selenocyanatophenyl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Organoselenocyanates and symmetrical diselenides redox modulators: Design, synthesis and biological evaluation

  摘要：

  Oxidative stress (OS) and disturbed intracellular redox balance have been predominantly observed in different types of cancer, including hepatocellular carcinoma (HCC). Agents which can stop OS multistressor events and modulate the intracellular redox state are becoming a major focus in HCC prevention. Among them, compounds with glutathione peroxidase (GPx)-like activity are of particularly concern. We herein report the synthesis of novel series of organoselenocyanates and symmetrical diselenide antioxidants, inspired by the natural redox enzyme, GPx and the synthetic organoselenium ebselen antioxidants. Their cytotoxic activity was evaluated against Hep G2 cells and their antimicrobial activities were evaluated against Candida albicans (C. albicans) fungus as well as against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus), gram-negative and gram-positive bacteria, respectively. These compounds were also tested for their antioxidant activities using 2,2-diphenyl-1-picrylhydrazyl (DPPH), GPx-like activity and bleomycin dependent DNA damage assays and a basic structure activity relationship was subsequently established. The physicochemical parameters and drug-likeness were computed employing the Molinspiration online property calculation toolkit and MolSoft software. Interestingly, some compounds proved to be more cytotoxic than ebselen and the known anticancer drug 5-Fu and in the same time they showed similar, sometime even more, antifungal activity than the reference antifungal drugs. Among these compounds, compound 16 was considered to be the most interesting with free radical-scavenging activity comparable to ascorbic acid and a GPx-like activity similar to ebselen. As most of these compounds comply with Lipinski's Rule of Five, they promise good bioavailability, which needs to be studied as part of future investigations. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.002
• 作为产物：
  描述：

  苯胺 在 selenium(IV) oxide 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 16.0h， 生成 (Z)-3-(4-selenocyanatophenylcarbamoyl)acrylic acid
  参考文献：
  名称：

  用于超快红外光谱的长振动寿命 R-硒氰酸酯探针：性质和合成

  摘要：

  超快红外振动光谱广泛用于研究从水到模型膜的系统动力学。由于实验观察窗口仅限于探针振动寿命的几倍，因此测量宽时间范围的一个常见障碍是分子振动寿命短（通常为几到几十皮秒）。已经合成了五种新的长寿命芳族硒氰酸酯振动探针并表征了它们的振动特性。将这些探针与市售的硒氰酸苯酯进行比较。在复杂溶剂中的振动寿命在~400 到 500 ps 之间，这是迄今为止报道的最长的室温振动寿命之一。与在 CCl 4等简单溶剂中长期存在的振动相比，但在复杂溶剂中变得更短，这里讨论的探针在复杂溶剂中具有约 400 ps 的寿命，在简单溶剂中甚至更长。其中之一在 CCl 4中具有 1235 ps 的非凡寿命。这些探针具有一系列分子大小和几何形状，由于空间原因，它们可用于放置到不同的复杂材料中，其中一些具有使其合成结合到更大分子（例如工业聚合物）中的功能。我们研究了一系列的给电子和吸电子的效果对- CN 拉伸振动特性的替代物。当根据

  DOI：

  10.1021/acs.jpcb.1c04939

文献信息

• Design, Synthesis, and Biological Evaluation of Novel Hydroxamic Acid-Based Organoselenium Hybrids
  作者：Jameelah S. Alotaibi、Yasair S. Al-Faiyz、Saad Shaaban

  DOI：10.3390/ph16030367

  日期：——

  We report the design and synthesis of novel hydroxamic acid-tethered organoselenium (OSe) hybrids. Their antimicrobial and anticancer activities were assessed against different microbes (e.g., Candida albicans (C. albicans), Escherichia coli (E. coli), and Staphylococcus aureus (S. aureus)), as well as liver and breast carcinomas. OSe hybrid 8 showed promising anticancer activity, with IC50 = 7.57

  我们报告了新型异羟肟酸系链有机硒 (OSe) 杂化物的设计和合成。评估了它们针对不同微生物（例如，白色念珠菌 (C. albicans)、大肠杆菌 (E. coli) 和金黄色葡萄球菌 (S. aureus)）以及肝癌和乳腺癌的抗菌和抗癌活性。OSe hybrid 8 显示出良好的抗癌活性，针对 HepG2 的 IC50 = 7.57 ± 0.5 µM，针对 MCF-7 细胞的 IC50 = 9.86 ± 0.7 µM。此外，OSe 化合物 8 和 15 表现出有前途的抗菌活性，特别是对白色念珠菌（IA% = 91.7 和 83.3）和金黄色葡萄球菌（IA% = 90.5 和 71.4）。最小抑菌浓度 (MIC) 测定证实了 OSe 化合物 8 的潜在抗菌活性。与 2 中的维生素 C 相比，OSe 化合物 8 和 16 显示出良好的抗氧化活性，
• Organoseleno cytostatic derivatives: Autophagic cell death with AMPK and JNK activation
  作者：Pablo Garnica、Ignacio Encío、Daniel Plano、Juan A. Palop、Carmen Sanmartín

  DOI：10.1016/j.ejmech.2019.04.074

  日期：2019.8

  Selenocyanates and diselenides are potential antitumor agents. Here we report two series of selenium derivatives related to selenocyanates and diselenides containing carboxylic, amide and imide moieties. These compounds were screened for their potency and selectivity against seven tumor cell lines and two non-malignant cell lines. Results showed that MCF-7 cells were especially sensitive to the treatment, with seven compounds presenting GI(50) values below 10 mu M. Notably, the carboxylic selenocyanate 8b and the cyclic imide 10a also displayed high selectivity for tumor cells. Treatment of MCF-7 cells with these compounds resulted in cell cycle arrest at S phase, increased levels of pJNK and pAMPK and caspase independent cell death. Autophagy inhibitors wortmannin and chloroquine partially prevented 8b and 10a induced cell death. Consistent with autophagy, increased Beclinl and LC3-IIB and reduced SQSTM1/p62 levels were detected. Our results point to 8b and 10a as autophagic cell death inducers. Published by Elsevier Masson SAS.