2-chloro-N-[5-(2-hydroxyphenyl)-[1,3,4]-thiadiazol-2-yl]-acetamide | 1248828-19-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-chloro-N-[5-(2-hydroxyphenyl)-[1,3,4]-thiadiazol-2-yl]-acetamide
• CAS: 1248828-19-4
• 化学式: C₁₀H₈ClN₃O₂S
• 分子量: 269.711
• InChiKey: WDFQQYDRFSXWNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  75.11
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-chloro-N-[5-(2-hydroxyphenyl)-[1,3,4]-thiadiazol-2-yl]-acetamide 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 5-benzylidene-2-[{5-(2-hydroxyphenyl)-[1,3,4]-thiadiazol-2-yl}imino]-1,3-thiazolidin-4-one
  参考文献：
  名称：

  噻二唑衍生物作为潜在的抗惊厥药

  摘要：

  一系列噻二唑衍生物通过不同取代的苯甲酸环合得到不同取代的噻唑烷-4-酮。元素分析、红外、$^1H$ NMR、$^{13}C$ NMR 和质谱数据证实了合成化合物的结构。这些基团的衍生物通过MES模型评估了它们的抗惊厥活性，并通过旋转棒方法评估了神经毒性。所合成的化合物显示出良好的抗惊厥活性潜力，此外，这些化合物还表现出神经毒性效应。观察发现，相比于具有未取代苯环的化合物[4(a-l)]，在苯环3, 4位带有$OCH_3$的化合物[5(a-l)]对抗惊厥的保护作用较弱。

  DOI：

  10.5012/bkcs.2011.32.3.1011
• 作为产物：
  描述：

  水杨酸 在 吡啶 、 三氯氧磷 作用下， 以 苯 为溶剂， 生成 2-chloro-N-[5-(2-hydroxyphenyl)-[1,3,4]-thiadiazol-2-yl]-acetamide
  参考文献：
  名称：

  噻二唑衍生物作为潜在的抗惊厥药

  摘要：

  一系列噻二唑衍生物通过不同取代的苯甲酸环合得到不同取代的噻唑烷-4-酮。元素分析、红外、$^1H$ NMR、$^{13}C$ NMR 和质谱数据证实了合成化合物的结构。这些基团的衍生物通过MES模型评估了它们的抗惊厥活性，并通过旋转棒方法评估了神经毒性。所合成的化合物显示出良好的抗惊厥活性潜力，此外，这些化合物还表现出神经毒性效应。观察发现，相比于具有未取代苯环的化合物[4(a-l)]，在苯环3, 4位带有$OCH_3$的化合物[5(a-l)]对抗惊厥的保护作用较弱。

  DOI：

  10.5012/bkcs.2011.32.3.1011

文献信息

• Synthesis, Characterization and Antimicrobial Activity of New Thiadiazole Derivatives
  作者：Pooja Mullick、Suroor A. Khan、Surajpal Verma、Ozair Alam

  DOI：10.5012/bkcs.2010.31.8.2345

  日期：2010.8.20

  A series of thiadiazole derivatives were synthesized with differently substituted benzoic acids which were cyclized to give differently substituted thiazolidin-4-one. Elemental analysis, IR, $^1H$ NMR, $^13}C$ NMR and mass spectral data confirmed the structure of the newly synthesized compounds. The derivatives of these moieties were evaluated for antimicrobial activity. Most of the synthesized compounds showed good antimicrobial activity at 200 and $100\;\mu}g/mL$. Compounds showed most significant antibacterial activity against gram negative test organism Escherichia coli and most significant antifungal activity against test organisms Aspergillus niger and Candida albicans. It was observed that compounds with $OCH_3$ at 3, 4 position of phenyl ring [5(a-l)] were more potent against microbes as compared to compounds having unsubstituted phenyl ring [4(a-l)].

  一系列噻二唑衍生物通过不同取代基的苯甲酸环化合成，得到了不同取代基的噻唑烷-4-酮。元素分析、红外、$^1H$ NMR、$^13}C$ NMR和质谱数据证实了新合成化合物的结构。这些基团的衍生物被评估了抗菌活性。大多数合成的化合物在200和$100\;\mu}g/mL$浓度下显示出良好的抗菌活性。化合物对革兰氏阴性试验菌大肠杆菌显示出最显著的抗菌活性，对试验菌黑曲霉和白色念珠菌显示出最显著的抗菌活性。观察到，与未取代苯环的化合物相比，苯环3, 4位有$OCH_3$的化合物[5(a-l)]对微生物的抑制作用更强。
• Further insight into the dual COX-2 and 15-LOX anti-inflammatory activity of 1,3,4-thiadiazole-thiazolidinone hybrids: The contribution of the substituents at 5th positions is size dependent
  作者：Yasser M. Omar、Samia G. Abdel-Moty、Hajjaj H.M. Abdu-Allah

  DOI：10.1016/j.bioorg.2020.103657

  日期：2020.4

  Herin we report the design, synthesis, full characterization and biological investigation of new 15-LOX/COX dual inhibitors based on 1,3-thiazolidin-4-one (15-lipoxygenase pharmacophore) and 1,3,4-thiadiazole (COX pharmacophore) scaffolds. This series of molecular modifications is an extension of a previously reported series to further explore the structural activity relationship. Compounds 3a, 4e, 4n, 4q, 7 and 8 capable of inhibiting 15-LOX at (2.74, 4.2, 3.41, 10.21, 3.71 and 3.36 mu M, respectively) and COX-2 at (0.32, 0.28, 0.28, 0.1, 0.28 and 0.27 mu M, respectively). The results revealed that binding to 15-LOX and COX is sensitive to the bulkiness of the substituents at the 5 positions. 15-LOX bind better with small substituents, while COXs bind better with bulky substituents. Compounds 3a, 4r and 4q showed comparable in vivo anti-inflammatory activity to the reference drug (celecoxib). The ulcer liability test showed no sign of ulceration which ensures the safe gastric profile. Docking study was performed to explore the possible mode of interaction of the new compounds with the active site of human 15-LOX and COX-2. This study discloses some structural features for binding to 15-LOX and COX, thus pave the way to design anti-inflammatory agents with balanced dual inhibition of these enzymes.