2-[[5-(4-甲氧基苯基)-1,3,4-噻二唑-2-基]氨基]-1,3-噻唑-4-酮 | 89335-18-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-[[5-(4-甲氧基苯基)-1,3,4-噻二唑-2-基]氨基]-1,3-噻唑-4-酮
• 英文名称: 2-[(5-(4-methoxyphenyl) -1,3,4-thiadiazol-2-yl)imino]-1,3-thiazolidin-4-one
• 英文别名: 2-((5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl)imino)thiazolidin-4-one；2-((5-(4-Methoxyphenyl)-1,3,4-thiadiazol-2-yl)amino)thiazol-4(5H)-one；(2E)-2-[[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]imino]-1,3-thiazolidin-4-one
• CAS: 89335-18-2
• 化学式: C₁₂H₁₀N₄O₂S₂
• 分子量: 306.369
• InChiKey: LWFGVNBGXCJVOR-UHFFFAOYSA-N

物化性质

• 熔点：
  198 °C(Solv: ethanol (64-17-5))
• 沸点：
  496.8±47.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[[5-(4-甲氧基苯基)-1,3,4-噻二唑-2-基]氨基]-1,3-噻唑-4-酮 在 溴 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 5-bromo-5-[bromo(phenyl)methyl]-2-[[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]amino]-1,3-thiazol-4-one
  参考文献：
  名称：

  Naik; Naik; Meher, Journal of the Indian Chemical Society, 1983, vol. 60, # 7, p. 674 - 678

  摘要：

  DOI：
• 作为产物：
  描述：

  大茴香酸 在 吡啶 、 三氯氧磷 作用下， 以 乙醇 、 苯 为溶剂， 生成 2-[[5-(4-甲氧基苯基)-1,3,4-噻二唑-2-基]氨基]-1,3-噻唑-4-酮
  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。
• Design, synthesis, and <i>in vitro</i> and <i>in silico</i> studies of 1,3,4-thiadiazole-thiazolidinone hybrids as carbonic anhydrase inhibitors
  作者：Narges Hosseini Nasab、Hussain Raza、Young Seok Eom、Mubashir Hassan、Andrzej Kloczkowski、Lloyd Christopher Chetty、Hendrik Gert Kruger、Song Ja Kim

  DOI：10.1039/d3nj01547e

  日期：——

  In this study, a series of 1,3,4-thiadiazole-thiazolidinone derivatives (7a–j) were synthesized as carbonic anhydrase inhibitors. The in vitro carbonic anhydrase inhibitory activity of these synthesized compounds was determined and the results revealed that compound 7i (IC50 = 0.402 ± 0.017 μM) is more potent than the standard reference acetazolamide (IC50 = 0.998 ± 0.046 μM). Moreover, kinetic analysis

  在本研究中，合成了一系列1,3,4-噻二唑-噻唑烷酮衍生物（7a-j ）作为碳酸酐酶抑制剂。测定了这些合成化合物的体外碳酸酐酶抑制活性，结果表明化合物7i (IC 50 = 0.402 ± 0.017 μM) 比标准参考乙酰唑胺 (IC 50 = 0.998 ± 0.046 μM)更有效。此外，还进行了动力学分析来观察与目标酶的结合方式，结果表明化合物7i以竞争的方式与目标绑定。对所有化合物进行了抗DPPH抗氧化活性和对A549（人肺癌细胞）抗癌活性的筛选，MTT测定结果表明化合物7a和7d具有更强的生长抑制作用。此外，根据分子对接研究，化合物7i在受体结合口袋内表现出良好的构象状态和氢键相互作用。因此，新型化合物7i可用作有效且选择性碳酸酐酶抑制剂的有前途的药效团。
• 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.
• NAIK, H.;NAIK, S. K.;MEHER, S. S.;NAYAK, A., J. INDIAN CHEM. SOC., 1983, 60, N 7, 674-678
  作者：NAIK, H.、NAIK, S. K.、MEHER, S. S.、NAYAK, A.

  DOI：——

  日期：——
• Thiadiazole Derivatives as Potential Anticonvulsant Agents
  作者：Pooja Mullick、Suroor A. Khan、Surajpal Verma、Ozair Alam

  DOI：10.5012/bkcs.2011.32.3.1011

  日期：2011.3.20

  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 synthesized compounds. The derivatives of these moieties were evaluated for anticonvulsant activity by MES model and neurotoxicity by rotarod method. The synthesized compounds showed good potential for anticonvulsant activity besides this, the compounds also showed neurotoxic effect. It was observed that compounds with $OCH_3$ at 3, 4 position of phenyl ring [5(a-l)] showed less protection against convulsions 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。