4-chloro-6-(4-nitrophenyl)pyrimidine | 954221-91-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-chloro-6-(4-nitrophenyl)pyrimidine
• CAS: 954221-91-1
• 化学式: C₁₀H₆ClN₃O₂
• 分子量: 235.63
• InChiKey: LDVMDTKPGMBFAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-6-(4-nitrophenyl)pyrimidine 在 盐酸 、 三乙胺 、 tin(ll) chloride 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 异丙醇 为溶剂， 反应 12.33h， 生成 3-methyl-N-(4-(6-((3-(trifluoromethyl)phenyl)amino)pyrimidin-4-yl)phenyl)benzenesulfonamide
  参考文献：
  名称：

  A novel pyrimidine derivatives with aryl urea, thiourea and sulfonamide moieties: Synthesis, anti-inflammatory and antimicrobial evaluation

  摘要：

  A series of novel 4-(3-(trifluoromethyl) phenylamino-6-(4-(3-arylureiodo/arylthioureido/arylsulfonamido)-pyrimidine derivatives of biological interest were prepared by the sequential Suzuki cross coupling, acid amination, reduction followed by reaction of resulting amine with different arylisocyantes or arylisothiocyantes or arylsulfonyl chlorides. All the synthesized compounds (1-25) were screened for their pro-inflammatory cytokines (TNF-alpha and IL-6) and antimicrobial activity (antibacterial and antifungal). Biological data revealed that among all the compounds screened, compounds 5, 6, 11, 12, 16 and 20 were found to have moderate to potent anti-inflammatory activity (up to 48-78% TNF-alpha and 56-96% IL-6 inhibitory activity) with reference to standard dexamethasone at 10 mu M. The compounds 10, 12, 13, 18, 20, 22, 24 and 25 found to have promising antimicrobial activity against all the selected pathogenic bacteria and fungi. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.092
• 作为产物：
  描述：

  1-溴-4-硝基苯 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium acetate 、 palladium diacetate 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成 4-chloro-6-(4-nitrophenyl)pyrimidine
  参考文献：
  名称：

  A novel pyrimidine derivatives with aryl urea, thiourea and sulfonamide moieties: Synthesis, anti-inflammatory and antimicrobial evaluation

  摘要：

  A series of novel 4-(3-(trifluoromethyl) phenylamino-6-(4-(3-arylureiodo/arylthioureido/arylsulfonamido)-pyrimidine derivatives of biological interest were prepared by the sequential Suzuki cross coupling, acid amination, reduction followed by reaction of resulting amine with different arylisocyantes or arylisothiocyantes or arylsulfonyl chlorides. All the synthesized compounds (1-25) were screened for their pro-inflammatory cytokines (TNF-alpha and IL-6) and antimicrobial activity (antibacterial and antifungal). Biological data revealed that among all the compounds screened, compounds 5, 6, 11, 12, 16 and 20 were found to have moderate to potent anti-inflammatory activity (up to 48-78% TNF-alpha and 56-96% IL-6 inhibitory activity) with reference to standard dexamethasone at 10 mu M. The compounds 10, 12, 13, 18, 20, 22, 24 and 25 found to have promising antimicrobial activity against all the selected pathogenic bacteria and fungi. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.092

文献信息

• Design, synthesis, and pharmacological evaluation of 4- or 6-phenyl-pyrimidine derivatives as novel and selective Janus kinase 3 inhibitors
  作者：Lei Shu、Chengjuan Chen、Xueting Huan、Hao Huang、Manman Wang、Jianqiu Zhang、Yile Yan、Jianming Liu、Tiantai Zhang、Dayong Zhang

  DOI：10.1016/j.ejmech.2020.112148

  日期：2020.4

  As non-receptor tyrosine kinases, Janus kinases (JAKs) have become an attractive target for the treatment of autoimmune diseases and cancers. JAKs play a pivotal role in innate immunity, inflammation, and hematopoiesis by mediating the signaling of numerous cytokines, growth factors, and interferons (IFNs). Selective inhibitors of a variety of JAK members are expected to inhibit pro-inflammatory cytokine-mediated

  作为非受体酪氨酸激酶，Janus激酶（JAKs）已成为治疗自身免疫性疾病和癌症的有吸引力的靶标。JAK通过介导多种细胞因子，生长因子和干扰素（IFN）的信号传导，在先天免疫，炎症和造血过程中发挥关键作用。各种JAK成员的选择性抑制剂有望抑制促炎性细胞因子介导的炎症和免疫反应，同时防止靶向其他亚型的JAK。在这项工作中，通过设计与JAK3中独特的半胱氨酸（Cys909）残基连接的共价结合链，将基于4-或6-苯基-嘧啶衍生物的选择性差的化合物改进为高效的选择性化合物。化合物12表现出有效的JAK3抑制活性（IC50 = 1。与其他JAK同工型（> 588倍）相比，具有极好的选择性。在细胞分析中，化合物12强烈抑制JAK3依赖性信号传导和T细胞增殖。此外，体内数据显示，化合物12在Balb / c小鼠中显着抑制了恶唑酮（OXZ）诱导的迟发型超敏反应。化合物12还显示出体面的药代动力学性质，并且适
• 4‐Iodopyrimidine Labeling Reveals Nuclear Translocation and Nuclease Activity for Both MIF and MIF2**
  作者：Zhangping Xiao、Deng Chen、Fabian Mulder、Shanshan Song、Petra E. Wouden、Robbert H. Cool、Barbro N. Melgert、Gerrit J. Poelarends、Frank J. Dekker

  DOI：10.1002/chem.202103030

  日期：2022.1.3

  based probe 8 for the selective labeling of MIF and MIF2. This enabled monitoring of the translocation of MIF2 from the cytoplasm to the nucleus upon methylnitronitrosoguanidine stimulation, which indicates a nuclease activity for MIF2 on human genomic DNA. Thus, we provide a tool for MIF and MIF2 localization study, as well as demonstrate a nuclease activity for MIF2.

  蛋白质运输是蛋白质功能化的重要步骤。我们报告了一种基于 4-碘嘧啶的探针8，用于选择性标记 MIF 和 MIF2。这使得能够监测甲基亚硝基胍刺激后 MIF2 从细胞质到细胞核的易位，这表明 MIF2 在人类基因组 DNA 上的核酸酶活性。因此，我们为 MIF 和 MIF2 定位研究提供了一个工具，并展示了 MIF2 的核酸酶活性。
• A novel pyrimidine derivatives with aryl urea, thiourea and sulfonamide moieties: Synthesis, anti-inflammatory and antimicrobial evaluation
  作者：Ashish P. Keche、Girish D. Hatnapure、Rajesh H. Tale、Atish H. Rodge、Satish S. Birajdar、Vandana M. Kamble

  DOI：10.1016/j.bmcl.2012.03.092

  日期：2012.5

  A series of novel 4-(3-(trifluoromethyl) phenylamino-6-(4-(3-arylureiodo/arylthioureido/arylsulfonamido)-pyrimidine derivatives of biological interest were prepared by the sequential Suzuki cross coupling, acid amination, reduction followed by reaction of resulting amine with different arylisocyantes or arylisothiocyantes or arylsulfonyl chlorides. All the synthesized compounds (1-25) were screened for their pro-inflammatory cytokines (TNF-alpha and IL-6) and antimicrobial activity (antibacterial and antifungal). Biological data revealed that among all the compounds screened, compounds 5, 6, 11, 12, 16 and 20 were found to have moderate to potent anti-inflammatory activity (up to 48-78% TNF-alpha and 56-96% IL-6 inhibitory activity) with reference to standard dexamethasone at 10 mu M. The compounds 10, 12, 13, 18, 20, 22, 24 and 25 found to have promising antimicrobial activity against all the selected pathogenic bacteria and fungi. (C) 2012 Elsevier Ltd. All rights reserved.