2-[(5-Amino-1,3,4-thiadiazol-2-yl)sulfanyl]-1-(4-nitrophenyl)ethanone | 294652-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(5-Amino-1,3,4-thiadiazol-2-yl)sulfanyl]-1-(4-nitrophenyl)ethanone
• CAS: 294652-88-3
• 化学式: C₁₀H₈N₄O₃S₂
• 分子量: 296.331
• InChiKey: UZYXSTSOXAKNDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[(5-Amino-1,3,4-thiadiazol-2-yl)sulfanyl]-1-(4-nitrophenyl)ethanone 在 盐酸 、 铜 、 碳酸氢钠 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1-ethyl-6-fluoro-1,4-dihydro-7-[4-{5-(2-oxo-2-(p-nitrophenyl)ethylthio)-1,3,4-thiadiazol-2-yl}piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial, antimycobacterial and docking studies of novel N-piperazinyl fluoroquinolones

  摘要：

  The present study deals with the synthesis of some novel fluoroquinolone derivatives as antibacterial and antitubercular agents. The titled compounds 7a-g and 8a-g were found to possess comparable or more potent activity than the reference compounds ciprofloxacin, norfloxacin, isoniazid and rifampicin. The synthesized compounds showed activity against S. aureus and C. bacterium, whereas poor activity was observed against P. aeruginosa and E. coli. These compounds were subjected to in vitro cytotoxicity study by MTT assay, and their selectivity index was calculated. Compound 7d was found to be the most efficient antimycobacterial agent amongst the series. Molecular docking revealed that synthesized derivatives and target proteins were actively involved in a binding pattern and had significant correlation with biological activity.Novel N-piperazinyl fluoroquinolone derivatives were synthesized and evaluated for their in vitro antibacterial, antimycobacterial and cytotoxic properties. Activity results were compared with the docking results.

  DOI：

  10.1007/s00044-012-0074-2
• 作为产物：
  描述：

  对硝基苯乙酮 在 aluminum (III) chloride 、 溴 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 2-[(5-Amino-1,3,4-thiadiazol-2-yl)sulfanyl]-1-(4-nitrophenyl)ethanone
  参考文献：
  名称：

  Synthesis and antibacterial, antimycobacterial and docking studies of novel N-piperazinyl fluoroquinolones

  摘要：

  The present study deals with the synthesis of some novel fluoroquinolone derivatives as antibacterial and antitubercular agents. The titled compounds 7a-g and 8a-g were found to possess comparable or more potent activity than the reference compounds ciprofloxacin, norfloxacin, isoniazid and rifampicin. The synthesized compounds showed activity against S. aureus and C. bacterium, whereas poor activity was observed against P. aeruginosa and E. coli. These compounds were subjected to in vitro cytotoxicity study by MTT assay, and their selectivity index was calculated. Compound 7d was found to be the most efficient antimycobacterial agent amongst the series. Molecular docking revealed that synthesized derivatives and target proteins were actively involved in a binding pattern and had significant correlation with biological activity.Novel N-piperazinyl fluoroquinolone derivatives were synthesized and evaluated for their in vitro antibacterial, antimycobacterial and cytotoxic properties. Activity results were compared with the docking results.

  DOI：

  10.1007/s00044-012-0074-2

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。