5-acetoxy-2-(chloroseleno)benzoyl chloride | 1381782-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 5-acetoxy-2-(chloroseleno)benzoyl chloride
• 英文别名: (3-Carbonochloridoyl-4-chloroselanylphenyl) acetate
• CAS: 1381782-06-4
• 化学式: C₉H₆Cl₂O₃Se
• 分子量: 312.011
• InChiKey: LQPJJZXYWIDPJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-acetoxy-2-(chloroseleno)benzoyl chloride 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of histone deacetylase inhibitors possessing glutathione peroxidase-like and antioxidant activities against Alzheimer’s disease

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2018.10.022
• 作为产物：
  描述：

  2-氨基-5-羟基苯甲酸 在 吡啶 、 氯化亚砜 、 sodium nitrite 作用下， 生成 5-acetoxy-2-(chloroseleno)benzoyl 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.
• 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.