5-cyano-6-(biphenyl-4-yl)-2-thiouracil | 1220709-70-5

• 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: 5-cyano-6-(biphenyl-4-yl)-2-thiouracil
• 英文别名: 4-oxo-6-(4-phenylphenyl)-2-sulfanylidene-1H-pyrimidine-5-carbonitrile
• CAS: 1220709-70-5
• 化学式: C₁₇H₁₁N₃OS
• 分子量: 305.36
• InChiKey: FFFZMDZGPXYYSJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-cyano-6-(biphenyl-4-yl)-2-thiouracil 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 4-([1,1'-biphenyl]-4-yl)-2-((4-azidobenzyl)thio)-6-methoxypyrimidine-5-carbonitrile
  参考文献：
  名称：

  Design, syntheses and evaluation of 4-oxo-5-cyano thiouracils as SecA inhibitors

  摘要：

  Protein translocation is essential for bacterial survival and the most important translocation mechanism is the secretion (Sec) pathway in which SecA is a central core driving force. Thus targeting SecA is a promising strategy for developing novel antibacterial therapeutics. Herein, we report the syntheses and evaluation of a series of nearly 60 4-oxo-5-cyano thiouracil derivatives based upon our previously reported core pyrimidine structure. Introduction of polar group such as -N-3 and linker groups such as -CH2-O- enhanced the potency several fold. Apart from being potential antibacterial agents, these inhibitors can be indispensable tools for biologists to probe the mechanism of protein translocation via the SecA machinery in bacteria. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.11.017
• 作为产物：
  描述：

  硫脲 、 氰乙酸乙酯 、 对苯基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 5-cyano-6-(biphenyl-4-yl)-2-thiouracil
  参考文献：
  名称：

  含有三唑并噻二唑作为SecA抑制剂的硫尿嘧啶衍生物的设计，合成和抗菌活性

  摘要：

  通过在先导SecA抑制剂2上进行结构修饰，合成了一系列含有三唑并噻二唑部分（7a-7l）的新型硫尿嘧啶衍生物。已经评估了所有化合物对解淀粉芽孢杆菌，金黄色葡萄球菌和枯草芽孢杆菌的抗菌活性。还测试了化合物7d和7g对SecA ATPase的抑制活性，这归因于它们有希望的抗菌活性。发现化合物7d的抑制活性高于2。分子对接工作表明化合物7d 可能在靠近ATPase ATP结合域的口袋处结合。

  DOI：

  10.1016/j.ejmech.2016.12.053

文献信息

• Synthesis, antibacterial activities and molecular docking study of thiouracil derivatives containing oxadiazole moiety
  作者：Peng-Lei Cui、Di Zhang、Xiu-Min Guo、Shu-Jing Ji、Qing-Mei Jiang

  DOI：10.1080/00397911.2021.1904990

  日期：——

  series of novel thiouracil derivatives 9 containing an oxadiazole moiety have been synthesized by structural modification of a lead SecA inhibitor, 2. These compounds have been evaluated for their antibacterial activities against Bacillus amyloliquefaciens, Staphylococcus aureus and Bacillus subtilis. Among them, compounds 9g and 9n exhibited promising antibacterial activities against the tested strains

  摘要 通过含铅SecA抑制剂2的结构修饰，合成了一系列含有恶二唑部分的新型硫尿嘧啶衍生物9。这些化合物已被评估其对淀粉芽孢杆菌，金黄色葡萄球菌和枯草芽孢杆菌的抗菌活性。其中，化合物9g和9n对被测菌株表现出有希望的抗菌活性。还测试了化合物9g对SecA ATPase的抑制活性，化合物9g的IC 50值为19.9μg / mL，低于化合物2的IC 50值。（20.8 µg / mL）。分子对接研究表明，化合物9g可能占据了SecA IRA2和NBD结构域形成的口袋。
• Synthesis and Antibacterial Evaluation of Thiouracil Derivatives Containing 1,2,4-Triazolo[1,5-a]Pyrimidine
  作者：Penglei Cui、Di Zhang、Xiumin Guo、Shujing Ji、Qingmei Jiang

  DOI：10.2174/1570178617999200826164227

  日期：2021.7

  :A series of new thiouracil compounds containing 1,2,4-triazolo[1,5-a]pyrimidine were designed and synthesized. The in vitro antibacterial activities of the new compounds against Bacillus amyloliquefaciens, Staphylococcus aureus and Bacillus subtilis were tested. The results showed that some of the new compounds had strong inhibitory activities against the tested bacteria. At the concentration of 50

  ：设计合成了一系列含有1,2,4-三唑并[1,5-a]嘧啶的新型硫氧嘧啶化合物。测试了新化合物对解淀粉芽孢杆菌、金黄色葡萄球菌和枯草芽孢杆菌的体外抗菌活性。结果表明，一些新化合物对受试细菌具有很强的抑制活性。在50 μg/mL的浓度下，化合物12d具有广谱和最高的抑制活性，对3个受试菌株均具有100%的抑制作用，与​​作为对照的诺氟沙星相同。
• Design, synthesis and antibacterial activities of thiouracil derivatives containing acyl thiourea as SecA inhibitors
  作者：Penglei Cui、Xiaoliu Li、Mengyuan Zhu、Binghe Wang、Jing Liu、Hua Chen

  DOI：10.1016/j.bmcl.2016.11.060

  日期：2017.5

  A series of novel thiouracil derivatives containing an acyl thiourea moiety (7a–7x) have been synthesized by structural modification of a lead SecA inhibitor, 2. All the compounds have been evaluated for their antibacterial activities against Bacillus amyloliquefaciens, Staphylococcus aureus, and Bacillus subtilis. Compounds 7c, 7m, 7u, 7v exhibited promising activities against above bacteria. Such

  通过对铅SecA抑制剂2进行结构修饰，合成了一系列含有酰基硫脲部分（7a – 7x）的新型硫尿嘧啶衍生物。所有化合物均已被评估对淀粉芽孢杆菌，金黄色葡萄球菌和枯草芽孢杆菌的抗菌活性。化合物7c，7m，7u，7v对上述细菌表现出有希望的活性。进一步测试了这四种化合物对SecA ATPase的抑制活性，结果表明化合物7c和7u具有比化合物2高的抑制活性。分子对接研究表明化合物7u可能在靠近ATPase ATP结合域的口袋处结合。
• The first low μM SecA inhibitors
  作者：Weixuan Chen、Ying-ju Huang、Sushma Reddy Gundala、Hsiuchin Yang、Minyong Li、Phang C. Tai、Binghe Wang

  DOI：10.1016/j.bmc.2009.12.074

  日期：2010.2

  SecA ATPase is a critical member of the Sec family, which is important in the translocation of membrane and secreted polypeptides/proteins in bacteria. Small molecule inhibitors can be very useful research tools as well as leads for future antimicrobial agent development. Based on previous virtual screening work, we optimized the structures of two hit compounds and obtained SecA ATPase inhibitors with IC50 in the single digit micromolar range. These represent the first low micromolar synthetic inhibitors of bacterial SecA and will be very useful for mechanistic studies. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis, antibacterial activity evaluation and molecular docking studies of coumarin modified thiouracil derivatives as SecA inhibitor
  作者：Hong Zhang、Penglei Cui、Xinming Hu、Hongya Li

  DOI：10.1080/00397911.2023.2272207

  日期：2023.12.17