2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-1-(4-fluorophenyl)ethanone | 401584-21-2

• 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)thio)-1-(4-fluorophenyl)ethanone
• 英文别名: 2-[(5-Amino-1,3,4-thiadiazol-2-YL)sulfanyl]-1-(4-fluorophenyl)-1-ethanone；2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]-1-(4-fluorophenyl)ethanone
• CAS: 401584-21-2
• 化学式: C₁₀H₈FN₃OS₂
• mdl: MFCD00110723
• 分子量: 269.323
• InChiKey: XMXFDTZPFFUNFM-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179 °C
• 沸点：
  482.6±51.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 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：
  122
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-1-(4-fluorophenyl)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-fluorophenyl)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：

  4-氟苯乙酮 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)thio)-1-(4-fluorophenyl)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, Synthesis, SAR and Molecular Modeling Studies of Novel Imidazo[2,1-<i>b</i>][1,3,4]Thiadiazole Derivatives as Highly Potent Antimicrobial Agents
  作者：Hakan Tahtaci、Hatice Karacık、Abdulilah Ece、Mustafa Er、Mine Gül Şeker

  DOI：10.1002/minf.201700083

  日期：2018.3

  In this study, a novel series of phenyl substituted imidazo[2,1‐b][1,3,4]thiadiazole derivatives were synthesized, characterized and explored for antibacterial activity against Gram‐negative Escherichia coli, Gram‐positive Staphylococcus aureus and Bacillus subtilis and antifungal activity against Candida albicans. Most of the synthesized compounds exhibited remarkable antimicrobial activities, some

  在这项研究中，合成了一系列新颖的苯基取代的咪唑并[2,1- b ] [1,3,4]噻二唑衍生物，表征并探讨了其对革兰氏阴性大肠杆菌，革兰氏阳性金黄色葡萄球菌和芽孢杆菌的抗菌活性。枯草芽孢杆菌及其对白色念珠菌的抑菌活性。大多数合成的化合物均显示出显着的抗菌活性，其中某些活性是阳性对照的十倍。最有前途的化合物显示出优异的活性，对金黄色葡萄球菌和枯草芽孢杆菌的MIC值为0.03μg/ ml 。（阳性化合物氯霉素的MIC值分别为0.4μg/ ml和0.85μg/ ml）。此外，还通过计算工具研究了结构-活动关系。还计算了化合物的一些理化性质和ADME性质。在PM6级进行的电子结构计算和使用Glide超精密模式进行的分子对接模拟的结合表明，在对位上没有吸电子取代基的酮基芳基环的疏水性增强了活性，而在第二个芳基环上的供电子取代基为对活动有害。
• 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。