2-(chloroselenyl)-5-fluorobenzoyl chloride | 1381782-04-2

• 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: 2-(chloroselenyl)-5-fluorobenzoyl chloride
• 英文别名: 5-fluoro-2-selenochlorobenzoyl chloride；5-fluoro-2-(chloroseleno)benzoyl chloride；(2-Carbonochloridoyl-4-fluorophenyl) selenohypochlorite；(2-carbonochloridoyl-4-fluorophenyl) selenohypochlorite
• CAS: 1381782-04-2
• 化学式: C₇H₃Cl₂FOSe
• 分子量: 271.965
• InChiKey: TWVPQXLXGPOLGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 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：
  2

反应信息

• 作为反应物：
  描述：

  2-(chloroselenyl)-5-fluorobenzoyl chloride 在 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以64%的产率得到5-fluoro-1,2-benzoisoselenazole-3(2H)-one
  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：

  2-氨基-5-氟苯甲酸 在 盐酸 、 氯化亚砜 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 生成 2-(chloroselenyl)-5-fluorobenzoyl chloride
  参考文献：
  名称：

  设计，合成和评估作为对抗阿尔茨海默氏病的多靶标配体的氯喹醇-依布硒啉杂种†

  摘要：

  设计，合成和评估了通过将金属螯合剂氯喹醇和抗氧化剂依布硒啉融合而获得的一系列新型化合物，这些化合物可作为针对阿尔茨海默氏病（AD）的多靶标配体。具体而言，与它们的母体化合物喹喔啉和依伯硒仑相比，这些杂种显示出显着的抑制自我和Cu（II）诱导的淀粉样β（Aβ）聚集的能力，并充当了杰出的抗氧化剂和生物金属螯合剂。此外，该杂种在依布硒啉相关的药理特性方面显示出显着改善，包括模仿谷胱甘肽过氧化物酶和清除H 2 O 2的能力。在这些分子中，化合物10h被确定为AD治疗的潜在先导化合物。重要的是，发现该化合物具有快速的H 2 O 2清除活性和谷胱甘肽过氧化物酶样（GPx样）活性。此外，化合物10h能够有效地分解预制的自我和Cu（II）诱导的Aβ聚集体。此外，在高达2000 mg kg -1的剂量下，10h能够穿透中枢神经系统（CNS），并且在小鼠中没有表现出任何急性毒性。

  DOI：

  10.1039/c5ra26797h

文献信息

• Computer-assisted designed “selenoxy–chinolin”: a new catalytic mechanism of the GPx-like cycle and inhibition of metal-free and metal-associated Aβ aggregation
  作者：Zhiren Wang、Yali Wang、Wenrui Li、Zhihong Liu、Zonghua Luo、Yang Sun、Ruibo Wu、Ling Huang、Xingshu Li

  DOI：10.1039/c5dt02130h

  日期：——

  Using support from rational computer-assisted design, a novel series of hybrids designed by fusing the metal-chelating agent CQ and the antioxidant ebselen were synthesized and evaluated as multitarget-directed ligands.

  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。
• 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。
• 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.
• Synthesis and antiproliferative evaluation of novel steroid-benzisoselenazolone hybrids
  作者：Jianguo Cui、Meizhen Wei、Liping Pang、Chunfang Gan、Junan Xiao、Haixin Shi、Junyan Zhan、Zhiping Liu、Yanmin Huang

  DOI：10.1016/j.steroids.2019.108502

  日期：2019.12

  The two different types of steroidal benzisoselenazolone hybrids were synthesized by incorporating benzisoselenazolone scaffold into dehydroepiandrosterone and B-norcholesterol. The antiproliferative activity of the synthesized compounds against some carcinoma cell lines were investigated. The results showed that some of these compounds have better inhibitory activity than abiraterone on the proliferation of tumor cells associated with human growth hormone, and have less cytotoxicity on normal human cells. In particular, the IC50 values of the compound 8a and 8f are 5.4 and 6.5 mu mol/L against human ovarian carcinoma (SKOV3) cell line, and possess SI values of 13.9 and 10.5, respectively. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs.
• Design, synthesis, and biological evaluation of histone deacetylase inhibitors possessing glutathione peroxidase-like and antioxidant activities against Alzheimer’s disease
  作者：Jinhui Hu、Baijiao An、Tingting Pan、Zhengcunxiao Li、Ling Huang、Xingshu Li

  DOI：10.1016/j.bmc.2018.10.022

  日期：2018.11

  A series of hybrids containing the pharmacophores of the histone deacetylase (HDAC) inhibitor, SAHA, and the antioxidant ebselen were designed and synthesized as multi-target-directed ligands against Alzheimer's disease. An in vitro assay indicated that some of these molecules exhibit potent HDAC inhibitory activity and ebselen-related pharmacological effects. Specifically, the optimal compound 7f was found to be a potent HDAC inhibitor (IC50 = 0.037 mu M), possessing rapid hydrogen peroxide scavenging activity and glutathione peroxidase-like activity (nu(0) = 150.0 mu M min(-1)) and good free oxygen radical absorbance capacity (value of ORAC: 2.2). Furthermore, compound 7f showed significant protective effects against damage induced by H2O2 and the ability to prevent ROS accumulation in PC12 cells.