5-((4-nitrophenyl)thio)-1,3,4-thiadiazol-2-amine | 78305-03-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-((4-nitrophenyl)thio)-1,3,4-thiadiazol-2-amine
• 英文别名: 5-(4-nitro-phenylsulfanyl)-[1,3,4]thiadiazol-2-ylamine；5-(4-Nitro-phenylmercapto)-[1,3,4]thiadiazol-2-ylamin；5-(4-nitrophenyl)sulfanyl-1,3,4-thiadiazol-2-amine
• CAS: 78305-03-0
• 化学式: C₈H₆N₄O₂S₂
• mdl: MFCD18429646
• 分子量: 254.293
• InChiKey: OPPQCJMYUXRMPV-UHFFFAOYSA-N

物化性质

• 熔点：
  196-200 °C
• 沸点：
  505.8±52.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-((4-nitrophenyl)thio)-1,3,4-thiadiazol-2-amine 在 双氧水 、 乙酸酐 、 溶剂黄146 作用下， 生成 N-[(4-nitro-benzenesulfonyl)-[1,3,4]thiadiazol-2-yl]-acetamide
  参考文献：
  名称：

  Some Chemotherapeutically Active Sulfones.¹ I

  摘要：

  DOI：

  10.1021/ja01220a049
• 作为产物：
  描述：

  4-nitrobenzenediazonium tetrafluoroborate 、 2-氨基-5-巯基-1,3,4-噻二唑 以 甲醇 、 乙腈 为溶剂， 反应 0.08h， 生成 5-((4-nitrophenyl)thio)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Discovery and development of substituted thiadiazoles as inhibitors of Staphylococcus aureus Sortase A

  摘要：

  High-throughput screening of small-molecule libraries has led to the identification of thiadiazoles as a new class of inhibitors against Staphylococcus aureus sortase A (SrtA). N-(5-((4-nitrobenzyl) thio)-1,3,4-thiadiazol-2-yl)nicotinamide (IC50= 3.8 mu M) was identified as a potent inhibitor of SrtA after synthetic modification of hit compounds. Additional ligands developed in this study displayed affinities in the low micromolar range without affecting bacterial growth in vitro. The study also suggest a new mode of action through covalent binding to the active site cysteine.

  DOI：

  10.1016/j.bmc.2019.115043

文献信息

• Monoazo dyestuffs for cellulose-containing fibers
  申请人：MITSUBISHI KASEI CORPORATION

  公开号：EP0121825B1

  公开（公告）日：1986-09-10
• US4837309A
  申请人：——

  公开号：US4837309A

  公开（公告）日：1989-06-06
• Some Chemotherapeutically Active Sulfones.¹ I
  作者：L. L. Bambas

  DOI：10.1021/ja01220a049

  日期：1945.4
• Discovery and development of substituted thiadiazoles as inhibitors of Staphylococcus aureus Sortase A
  作者：Patrick M. Wehrli、Ivana Uzelac、Thomas Olsson、Tomas Jacso、Daniel Tietze、Johan Gottfries

  DOI：10.1016/j.bmc.2019.115043

  日期：2019.10

  High-throughput screening of small-molecule libraries has led to the identification of thiadiazoles as a new class of inhibitors against Staphylococcus aureus sortase A (SrtA). N-(5-((4-nitrobenzyl) thio)-1,3,4-thiadiazol-2-yl)nicotinamide (IC50= 3.8 mu M) was identified as a potent inhibitor of SrtA after synthetic modification of hit compounds. Additional ligands developed in this study displayed affinities in the low micromolar range without affecting bacterial growth in vitro. The study also suggest a new mode of action through covalent binding to the active site cysteine.