4-(3-chlorophenyl)-5-(4-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3-chlorophenyl)-5-(4-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
• 英文别名: 4-(3-chlorophenyl)-3-(4-fluorophenyl)-1H-1,2,4-triazole-5-thione
• 化学式: C₁₄H₉ClFN₃S
• mdl: MFCD05257280
• 分子量: 305.763
• InChiKey: HVSRRNOLLLMHOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 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：
  59.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溴乙酸 、 4-(3-chlorophenyl)-5-(4-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 在 potassium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 2-[[4-(3-Chlorophenyl)-5-(4-fluorophenyl)-1,2,4-triazol-3-yl]sulfanyl]acetic acid
  参考文献：
  名称：

  Discovery of Protein–Protein Interaction Inhibitors of Replication Protein A

  摘要：

  Replication protein A (RPA) is a ssDNA binding protein that is essential for DNA replication and repair. The initiation of the DNA damage response by RPA is mediated by protein protein interactions involving the N-terminal domain of the 70 kDa subunit with partner proteins. Inhibition of these interactions increases sensitivity toward DNA damage and replication stress and may therefore be a potential strategy for cancer drug discovery. Toward this end, we have discovered two lead series of compounds, derived from hits obtained from a fragment-based screen that bind to RPA70N with low micromolar affinity and inhibit the binding of an ATRIP-derived peptide to RPA. These compounds may offer a promising starting point for the discovery of clinically useful RP inhibitors.

  DOI：

  10.1021/ml400032y
• 作为产物：
  描述：

  4-氟苯甲酰肼 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.25h， 生成 4-(3-chlorophenyl)-5-(4-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  1,2,4-三唑衍生的曼尼希碱的合成与抗菌评价。

  摘要：

  合成了一系列新型曼尼希碱，并评估了它们对革兰氏阳性和革兰氏阴性细菌菌株的体外抗菌活性。结果表明，所有化合物的活性均低于用作参考药物的活性，但其中一些对表皮葡萄球菌ATCC 12228和枯草芽孢杆菌ATCC 6633具有中等效力。哌嗪4位上存在苯环似乎是必要的在这类化合物中具有抗菌活性。

  DOI：

  10.1002/cbdv.201900377

文献信息

• Synthesis and Antibacterial Evaluation of Mannich Bases Derived from 1,2,4‐Triazole
  作者：Agata Paneth、Nazar Trotsko、Łukasz Popiołek、Agnieszka Grzegorczyk、Tomasz Krzanowski、Sara Janowska、Anna Malm、Monika Wujec

  DOI：10.1002/cbdv.201900377

  日期：2019.10

  The series of novel Mannich bases were synthesized and evaluated for their in vitro antibacterial activity against Gram-positive and Gram-negative bacterial strains. The results showed that all compounds were less active than the drugs used as reference, but some of them had moderate potency against Staphylococcus epidermidis ATCC 12228 and Bacillus subtilis ATCC 6633. The presence of a phenyl ring

  合成了一系列新型曼尼希碱，并评估了它们对革兰氏阳性和革兰氏阴性细菌菌株的体外抗菌活性。结果表明，所有化合物的活性均低于用作参考药物的活性，但其中一些对表皮葡萄球菌ATCC 12228和枯草芽孢杆菌ATCC 6633具有中等效力。哌嗪4位上存在苯环似乎是必要的在这类化合物中具有抗菌活性。
• Discovery of Protein–Protein Interaction Inhibitors of Replication Protein A
  作者：James D. Patrone、J. Phillip Kennedy、Andreas O. Frank、Michael D. Feldkamp、Bhavatarini Vangamudi、Nicholas F. Pelz、Olivia W. Rossanese、Alex G. Waterson、Walter J. Chazin、Stephen W. Fesik

  DOI：10.1021/ml400032y

  日期：2013.7.11

  Replication protein A (RPA) is a ssDNA binding protein that is essential for DNA replication and repair. The initiation of the DNA damage response by RPA is mediated by protein protein interactions involving the N-terminal domain of the 70 kDa subunit with partner proteins. Inhibition of these interactions increases sensitivity toward DNA damage and replication stress and may therefore be a potential strategy for cancer drug discovery. Toward this end, we have discovered two lead series of compounds, derived from hits obtained from a fragment-based screen that bind to RPA70N with low micromolar affinity and inhibit the binding of an ATRIP-derived peptide to RPA. These compounds may offer a promising starting point for the discovery of clinically useful RP inhibitors.