5-chloro-2-selenochlorobenzoyl chloride | 106966-88-5

• 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: 5-chloro-2-selenochlorobenzoyl chloride
• 英文别名: 5-chloro-2-(chloroseleno)benzoyl chloride；(2-Carbonochloridoyl-4-chlorophenyl) selenohypochlorite
• CAS: 106966-88-5
• 化学式: C₇H₃Cl₃OSe
• 分子量: 288.419
• InChiKey: IWLDDCHEKQJIBO-UHFFFAOYSA-N

物化性质

• 沸点：
  353.3±32.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-chloro-2-selenochlorobenzoyl chloride 在 ammonium hydroxide 、 Cp*Rh(CH₃CN)₃(SbF₆)₂ 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  将硒掺入DNA编码库中的化学。

  摘要：

  常规的直接CH H硒化反应具有简单的硒化，有限的原子经济性和复杂的反应体系。在这项工作中，我们设计了苯并硒氮酮作为一种新型的双功能硒化物试剂，用于在铑（III）催化下进行脱氢和脱氢CHH硒化反应。我们表明，使用苯并硒氮唑酮允许以快速，有效的方式生产一系列含有相邻氨基酰基的硒化产物，并具有较高的原子经济性。通过利用酰胺官能团作为亲核试剂，导向基团和酰胺偶联伙伴，证明了该方法的合成应用。这项工作显示出在促进快速构建含硒DNA编码化学文库（SeDEL）方面的巨大潜力，并为开发含硒药物奠定了基础。

  DOI：

  10.1002/anie.202003595
• 作为产物：
  描述：

  5,5'-dichloro-2,2'-(diselanediyl)dibenzoic acid 在 氯化亚砜 作用下， 生成 5-chloro-2-selenochlorobenzoyl chloride
  参考文献：
  名称：

  Computer-assisted designed “selenoxy–chinolin”: a new catalytic mechanism of the GPx-like cycle and inhibition of metal-free and metal-associated Aβ aggregation

  摘要：

  利用理性计算机辅助设计的支持，通过融合金属螯合剂CQ和抗氧化剂ebselen设计的新型混合物系列被合成并评估为多靶点定向配体。

  DOI：

  10.1039/c5dt02130h

文献信息

• 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.
• Design, synthesis, and biological evaluation of benzoselenazole-stilbene hybrids as multi-target-directed anti-cancer agents
  作者：Jun Yan、Yueyan Guo、Yali Wang、Fei Mao、Ling Huang、Xingshu Li

  DOI：10.1016/j.ejmech.2015.03.030

  日期：2015.5

  To identify novel multi-target-directed drug candidates for the treatment of cancer, a series of benzoselenazole-stilbene hybrids were synthesised by combining the pharmacophores of resveratrol and ebselen. The biological assay indicated that all of the hybrids exhibited antiproliferative activities against four human cancer cell lines and demonstrated good TrxR inhibitory activities. The mechanism of cell apoptosis was investigated in G2/M cell cycle arrest induced by compound 6e and the apoptosis of the human liver carcinoma Bel-7402 cell line. The significant increase in intracellular ROS confirmed that compound 6e was capable of causing oxidative stress-induced apoptosis in cancer cells. Our results support the potential of compound 6e as a candidate for further studies examining the development of novel drugs for cancer treatment. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Synthesis and evaluation of 8-hydroxyquinolin derivatives substituted with (benzo[d][1,2]selenazol-3(2H)-one) as effective inhibitor of metal-induced Aβ aggregation and antioxidant
  作者：Bo Wang、Zhiren Wang、Hong Chen、Chuan-Jun Lu、Xingshu Li

  DOI：10.1016/j.bmc.2016.08.017

  日期：2016.10

  A series of 8-hydroxyquinolin derivatives substituted with (benzo[d][1,2]selenazol-3(2H)-one) at the 2 position were synthesized and evaluated for treatment of Alzheimer's disease. In vitro assays demonstrated that most of the target compounds exhibit significant inhibition of Cu(II)-induced A beta(1-42) aggregation, rapid H2O2 scavenging and glutathione peroxidise (GPx)-like catalytic activity. Among these molecules, compound 9a is the most potent peroxide scavenger that possesses the ability to scavenge most H2O2 within 200-220 mm and possesses GPx-like activity (v(0) = 106.0 mu M.min(-1)), enabling modulation of metal -induced All aggregation. (C) 2016 Elsevier Ltd. All rights reserved.
• Novel tacrine–ebselen hybrids with improved cholinesterase inhibitory, hydrogen peroxide and peroxynitrite scavenging activity
  作者：Fei Mao、Jianwen Chen、Qi Zhou、Zonghua Luo、Ling Huang、Xingshu Li

  DOI：10.1016/j.bmcl.2013.10.034

  日期：2013.12

  A series of tacrine-ebselen hybrids were synthesised and evaluated as possible multifunctional anti-Alzheimer's disease (AD) agents. Compound 6i, which is tacrine linked with 5,6-dimethoxybenzo[d][1,2]selenazol-3(2H)-one by a six-carbon spacer, was the most potent acetylcholinesterase (AChE) and butylcholinesterase (BuChE) inhibitor, with IC50 values of 2.55 and 2.80 nM, respectively. Furthermore, this compound demonstrated similar hydrogen peroxide and peroxynitrite scavenging activity as ebselen by horseradish peroxidase assay and peroxynitrite scavenging activity assay, indicating that this hybrid is a good multifunctional drug candidate for the treatment of AD. (C) 2013 Elsevier Ltd. All rights reserved.
• EP4112608
  申请人：——

  公开号：——

  公开（公告）日：——