5-(4-(difluoromethylthio)phenylamino)-1,3,4-thiadiazole-2-thiol | 571149-73-0

• 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-(difluoromethylthio)phenylamino)-1,3,4-thiadiazole-2-thiol
• 英文别名: 5-({4-[(Difluoromethyl)sulfanyl]phenyl}amino)-1,3,4-thiadiazole-2-thiol；5-[4-(difluoromethylsulfanyl)anilino]-3H-1,3,4-thiadiazole-2-thione
• CAS: 571149-73-0
• 化学式: C₉H₇F₂N₃S₃
• mdl: MFCD03980955
• 分子量: 291.369
• InChiKey: CCTGGHGFEBPUHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(4-(difluoromethylthio)phenylamino)-1,3,4-thiadiazole-2-thiol 、 2-溴-5-硝基噻唑 在 甲醇 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.08h， 以89%的产率得到BI-90F3
  参考文献：
  名称：

  Synthesis and optimization of thiadiazole derivatives as a novel class of substrate competitive c-Jun N-terminal kinase inhibitors

  摘要：

  A series of thiadiazole derivatives has been designed as potential allosteric, substrate competitive inhibitors of the protein kinase JNK. We report on the synthesis, characterization and evaluation of a series of compounds that resulted in the identification of potent and selective JNK inhibitors targeting its JIP-1 docking site. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.013

文献信息

• Synthesis and structure–activity relationships of novel lincomycin derivatives. Part 1. Newly generated antibacterial activities against Gram-positive bacteria with erm gene by C-7 modification
  作者：Yoshinari Wakiyama、Ko Kumura、Eijiro Umemura、Kazutaka Ueda、Satomi Masaki、Megumi Kumura、Hideki Fushimi、Keiichi Ajito

  DOI：10.1038/ja.2015.119

  日期：2016.5

  7(S)-7-deoxy-7-arylthiolincomycin derivatives possessing a heterocyclic ring at the C-7 position via sulfur atom by either Mitsunobu reaction of 2,3,4-tris-O-(trimethylsiliyl)lincomycin or SN2 reaction of 7-O-methanesulfonyl-2,3,4-tri-O-trimethylsiliyllincomycin. As a result, 7(S)-7-deoxy-7-arylthiolincomycin derivatives 16, 21 and 27 exhibited antibacterial activities against respiratory infection-related

  我们通过2,3,4-tris-O-（trimethylsiliyl）lincomycin的Mitsunobu反应或SN2反应合成了通过硫原子在C-7位具有杂环的7（S）-7-脱氧-7-芳基硫代林霉素衍生物7-O-甲磺酰基-2,3,4-三-O-三甲基硅烷基林可霉素。结果，尽管克林霉素对那些病原体没有任何活性，但是7（S）-7-脱氧-7-芳基硫代林可霉素衍生物16、21和27对具有erm基因的呼吸道感染相关的革兰氏阳性细菌表现出抗菌活性。此外，从在7位的16（S-构型）和30（R-构型）的构型的比较结果，发现林可霉素衍生物的7（S）构型对于增强抗菌活性是必要的。
• Synthesis and optimization of thiadiazole derivatives as a novel class of substrate competitive c-Jun N-terminal kinase inhibitors
  作者：Surya K. De、Vida Chen、John L. Stebbins、Li-Hsing Chen、Jason F. Cellitti、Thomas Machleidt、Elisa Barile、Megan Riel-Mehan、Russell Dahl、Li Yang、Aras Emdadi、Ria Murphy、Maurizio Pellecchia

  DOI：10.1016/j.bmc.2009.12.013

  日期：2010.1

  A series of thiadiazole derivatives has been designed as potential allosteric, substrate competitive inhibitors of the protein kinase JNK. We report on the synthesis, characterization and evaluation of a series of compounds that resulted in the identification of potent and selective JNK inhibitors targeting its JIP-1 docking site. (C) 2009 Elsevier Ltd. All rights reserved.