5-cyano-6-(4-ethylphenyl)-2-thiouracil | 303062-09-1

• 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: 5-cyano-6-(4-ethylphenyl)-2-thiouracil
• 英文别名: 6-(4-ethylphenyl)-4-oxo-2-sulfanylidene-1H-pyrimidine-5-carbonitrile
• CAS: 303062-09-1
• 化学式: C₁₃H₁₁N₃OS
• 分子量: 257.316
• InChiKey: AOROGSGMECMRSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  1,4-二(溴甲基)苯 、 5-cyano-6-(4-ethylphenyl)-2-thiouracil 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以96%的产率得到2-[[4-[[5-cyano-4-(4-ethylphenyl)-6-oxo-1H-pyrimidin-2-yl]sulfanylmethyl]phenyl]methylsulfanyl]-4-(4-ethylphenyl)-6-oxo-1H-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  The first low μM SecA inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.12.074
• 作为产物：
  描述：

  硫脲 、 氰乙酸乙酯 、 4-乙基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 以25%的产率得到5-cyano-6-(4-ethylphenyl)-2-thiouracil
  参考文献：
  名称：

  The first low μM SecA inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.12.074

文献信息

• Design, Synthesis and Evaluation of Triazole-Pyrimidine Analogues as SecA Inhibitors
  作者：Jianmei Cui、Jinshan Jin、Arpana Sagwal Chaudhary、Ying-hsin Hsieh、Hao Zhang、Chaofeng Dai、Krishna Damera、Weixuan Chen、Phang C. Tai、Binghe Wang

  DOI：10.1002/cmdc.201500447

  日期：2016.1

  SecA, a key component of the bacterial Sec‐dependent secretion pathway, is an attractive target for the development of new antimicrobial agents. Through a combination of virtual screening and experimental exploration of the surrounding chemical space, we identified a hit bistriazole SecA inhibitor, SCA‐21, and studied a series of analogues by systematic dissections of the core scaffold. Evaluation

  SecA 是细菌 Sec 依赖性分泌途径的关键组成部分，是开发新型抗菌药物的一个有吸引力的靶点。通过虚拟筛选和对周围化学空间的实验探索相结合，我们鉴定了一种热门的双三唑 SecA 抑制剂 SCA-21，并通过对核心支架的系统解剖研究了一系列类似物。对这些类似物的评估使我们能够在 SecA 抑制中建立初步的结构-活性关系。该组中最好的化合物是低至亚微摩尔浓度的 SecA 依赖性蛋白质传导通道活性和蛋白质易位活性的有效抑制剂。它们还具有针对各种细菌菌株的最小抑菌浓度 (MIC) 值，与 SecA 和蛋白质易位抑制数据密切相关。这些化合物可有效对抗具有不同水平外排泵活性的耐甲氧西林金黄色葡萄球菌菌株，表明 SecA 抑制剂具有消除多药耐药性影响的能力。药物亲和力响应靶点稳定性和蛋白质下拉测定的研究结果与 SecA 作为这些化合物的靶点一致。
• 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.