N-(5-((4-nitrobenzyl)thio)-1,3,4-thiadiazol-2-yl)nicotinamide | 1242283-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(5-((4-nitrobenzyl)thio)-1,3,4-thiadiazol-2-yl)nicotinamide
• 英文别名: N-[5-[(4-nitrophenyl)methylsulfanyl]-1,3,4-thiadiazol-2-yl]pyridine-3-carboxamide
• CAS: 1242283-93-7
• 化学式: C₁₅H₁₁N₅O₃S₂
• 分子量: 373.416
• InChiKey: ZTDOJPCUIXALSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  167
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  对硝基溴化苄 在 吡啶 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 30.0h， 生成 N-(5-((4-nitrobenzyl)thio)-1,3,4-thiadiazol-2-yl)nicotinamide
  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

• Design and Synthesis of Thiadiazoles and Thiazoles Targeting the Bcr-Abl T315I Mutant: from Docking False Positives to ATP-Noncompetitive Inhibitors
  作者：Marco Radi、Emmanuele Crespan、Federico Falchi、Vincenzo Bernardo、Samantha Zanoli、Fabrizio Manetti、Silvia Schenone、Giovanni Maga、Maurizio Botta

  DOI：10.1002/cmdc.201000066

  日期：——

  previously identified dual Src/Abl hits, a new series of 1,3,4‐thiadiazoles and 1,3‐thiazoles were designed and synthesized, paying particular attention to the reduction of their lipophilicity and to the improvement of the affinity towards the drug‐resistant T315I mutant. Compound 5 was identified as a promising allosteric inhibitor of the T315I mutant.

  克服耐药性：为了优化我们先前确定的双重Src / Abl命中率，设计并合成了一系列新的1,3,4-噻二唑和1,3-噻唑，特别注意降低它们的亲脂性和对耐药T315I突变体亲和力的提高。化合物5被确定为T315I突变体的有希望的变构抑制剂。