6,6'-二硒二-(3-硝基苯甲酸) | 80180-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 6,6'-二硒二-(3-硝基苯甲酸)
• 中文别名: 9-氟-11&amp#x3B2,17-二羟基-16&amp#x3B2-甲基孕-1,4-二烯-3,20-二酮17-丙酸盐
• 英文名称: 6,6'-diselanediylbis(3-nitrobenzoic acid)
• 英文别名: 6,6'-Diselenobis-(3-nitrobenzoic acid)；2-[(2-carboxy-4-nitrophenyl)diselanyl]-5-nitrobenzoic acid
• CAS: 80180-68-3
• 化学式: C₁₄H₈N₂O₈Se₂
• 分子量: 490.146
• InChiKey: DSWCVZVEOQOMDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.17
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  166
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6,6'-二硒二-(3-硝基苯甲酸) 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-Nitro-2-[2-(5-nitro-3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one
  参考文献：
  名称：

  Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy

  摘要：

  Thioredoxin reductase (TrxR) is critical for cellular redox regulation and is involved in tumor proliferation, apoptosis and metastasis. Its C-terminal redox-active center contains a cysteine (Cys497) and a unique selenocysteine (Sec498), which are exposed to solvent and easily accessible. Thus, it is becoming an important target for anticancer drugs. Selective inhibition of TrxR by 1,2-(bis-1,2-benzisoselenazol-3(2H)-one)ethane (4a) prevents proliferation of several cancer cell lines both in vivo and in vitro. Using the structure of 4a as a starting point, a series of novel bis-1,2-benzisoselenazol-3(2H)-ones was designed, prepared and tested to explore the structure-activity relationships (SARs) for this class of inhibitor and to improve their potency. Notably, 1,2-(5,5'-dimethoxybis(1,2-benzisoselenazol-3(2H)-one))ethane (12) was found to be more potent than 4a in both in vitro and in vivo evaluation. Its binding sites were confirmed by biotin-conjugated iodoacetamide assay and a SAR model was generated to guide further structural modification. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.033
• 作为产物：
  描述：

  2-氯-5-硝基苯甲酸 在 甲烷磺酸 、 L-1,4-二硫代苏糖醇 、 苯甲醚 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.25h， 生成 6,6'-二硒二-(3-硝基苯甲酸)
  参考文献：
  名称：

  二硒化物介导的氢磷酰基化合物的催化功能化。

  摘要：

  我们报告了二芳基二硒化物催化剂的氢磷酰基化合物的交叉脱氢亲核功能化。拟议的有机催化循环非常类似于Atherton-Todd反应的机理，该催化剂可作为命名反应中所用卤化剂的可循环类似物。磷和硒的NMR研究表明存在P-Se键中间体，结构分析表明存在立体特异性反应。

  DOI：

  10.1021/acs.orglett.0c01858

文献信息

• Aerobic, Diselenide-Catalyzed Redox Dehydration: Amides and Peptides
  作者：Srirama Murthy Akondi、Pavankumar Gangireddy、Thomas C. Pickel、Lanny S. Liebeskind

  DOI：10.1021/acs.orglett.7b03620

  日期：2018.2.2

  At 2.5 mol % loadings using reaction temperatures between 30–55 °C, ortho-functionalized diaryl diselenides are highly effective organocatalytic oxidants for aerobic redox dehydrative amidic and peptidic bond formation using triethyl phosphite as a simple terminal reductant. This simple-to-perform organocatalytic reaction relies on the ability of selenols to react directly with dioxygen in air without

  在反应温度为30-55°C的条件下，负载量为2.5 mol％时，邻官能化的二芳基二硒化物是高效的有机催化氧化剂，可利用亚磷酸三乙酯作为简单的末端还原剂来形成需氧氧化还原脱水的酰胺和肽键。这种简单易行的有机催化反应依赖于硒醇与空气中的双氧直接反应而不依赖金属催化剂的能力。它代表了开发通用，经济且良性的催化氧化还原脱水方案的重要一步。
• 苯并异硒唑酮类化合物代谢物、其合成方法及 其应用
  申请人：南京凯熙医学科技有限公司

  公开号：CN106146371B

  公开（公告）日：2018-05-15

  本发明提供一种具有通式(Ⅰ)的苯并异硒唑衍生物或其药物学上可接受的盐：其中：R1、R2相同或不同，各自独立为氢、卤素(例如F、Cl)、腈基、硝基、C1‑C6烷基、C1‑C6烷氧基、C1‑C6烷硫基、N(C1‑C6烷基)2、NH(C1‑C6烷基)、COOH、SO3H。本发明还提供包含该化合物的药用组合物及其在制备抗肿瘤药物中的应用。
• Model compounds for the active site selenocysteine of glutathione peroxidase: A77Se NMR study
  作者：Diane Dowd、Peter Gettins

  DOI：10.1002/mrc.1260260102

  日期：1988.1

  To test the feasibility of using 77Se NMR to distinguish between different proposed mechanisms of action of the selenoenzyme glutathione peroxidase, model compounds containing the proposed selenium moieties have been synthesized and their 77Se NMR spectra recorded. It was found that the difference in chemical shift between the two proposed resting states, selenol or selenenic acid, is approximately

  为了测试使用 77Se NMR 区分硒酶谷胱甘肽过氧化物酶的不同拟议作用机制的可行性，合成了含有拟议硒部分的模型化合物，并记录了它们的 77Se NMR 光谱。发现两种建议的静止状态硒醇或硒酸之间的化学位移差异约为 1300 ppm。对于下一步，通过过氧化氢进行氧化，发现硒酸和硒酸种​​类之间的差异要小得多，约为 100 ppm。第二个反应步骤的产物，硫化硒与硫化硒，化学位移相差约 470 ppm。得出的结论是，对于酶的三种状态中的两种，原则上 77Se NMR 可以明确用于区分两种提议的机制。
• Conversion of Phenols into Selenophenols: Seleno Newman-Kwart Rearrangement
  作者：Anne Sørensen、Brian Rasmussen、Shubham Agarwal、Magnus Schau-Magnussen、Theis I. Sølling、Michael Pittelkow

  DOI：10.1002/anie.201303773

  日期：2013.11.18

  A ‘Se'lling point: The first thermally induced OAr→SeAr migration reaction is reported, and it can be used to prepare aryl selenols in three steps from the corresponding phenols. O‐aryl selenocarbamates rearrange to Se‐aryl carbamates via a four‐membered transition state (see scheme). The aryl selenols (isolated as the diselenides) can be prepared by hydrolysis of the Se‐aryl selenocarbamates.

  “沸点”：报道了第一个热诱导的O Ar →Se Ar迁移反应，它可用于从相应的苯酚分三步制备芳基硒醇。O-芳基硒代氨基甲酸酯通过四元过渡态重排为Se-芳基氨基甲酸酯（参见方案）。可以通过水解Se-芳基硒代氨基甲酸酯制备芳基硒醇（分离为二硒化物）。
• Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy
  作者：Jie He、Dongdong Li、Kun Xiong、Yongjie Ge、Hongwei Jin、Guozhou Zhang、Mengshi Hong、Yongliang Tian、Jin Yin、Huihui Zeng

  DOI：10.1016/j.bmc.2012.04.033

  日期：2012.6

  Thioredoxin reductase (TrxR) is critical for cellular redox regulation and is involved in tumor proliferation, apoptosis and metastasis. Its C-terminal redox-active center contains a cysteine (Cys497) and a unique selenocysteine (Sec498), which are exposed to solvent and easily accessible. Thus, it is becoming an important target for anticancer drugs. Selective inhibition of TrxR by 1,2-(bis-1,2-benzisoselenazol-3(2H)-one)ethane (4a) prevents proliferation of several cancer cell lines both in vivo and in vitro. Using the structure of 4a as a starting point, a series of novel bis-1,2-benzisoselenazol-3(2H)-ones was designed, prepared and tested to explore the structure-activity relationships (SARs) for this class of inhibitor and to improve their potency. Notably, 1,2-(5,5'-dimethoxybis(1,2-benzisoselenazol-3(2H)-one))ethane (12) was found to be more potent than 4a in both in vitro and in vivo evaluation. Its binding sites were confirmed by biotin-conjugated iodoacetamide assay and a SAR model was generated to guide further structural modification. (C) 2012 Elsevier Ltd. All rights reserved.