2,6-bis(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole | 1393846-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,6-bis(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole
• CAS: 1393846-21-3
• 化学式: C₁₈H₁₅N₃O₂S
• 分子量: 337.402
• InChiKey: CAKMZXJBQRJKTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-bis(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole 、 1-溴-4-硝基苯 在 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以81%的产率得到2,6-bis(4-methoxyphenyl)-5-(4-nitrophenyl)imidazo[2,1-b][1,3,4]thiadiazole
  参考文献：
  名称：

  2,6-二取代咪唑并[2,1-b][1,3,4]噻二唑的钯催化直接芳基化

  摘要：

  这项工作报告了使用 C–H 芳基化过程合成三芳基咪唑并 [2,1-b][1,3,4] 噻二唑衍生物的原始合成方法。反应范围证明了每个取代基的电子效应对反应效率的关键重要性。此外，在 2-溴-6-芳基咪唑 [2,1-b][1,3,4] 噻二唑衍生物的 C-2 和 C-5 位置进行了双重有效的“一锅法”功能化。使用顺序 Suzuki-Miyaura-C-H 芳基化级联程序实现。

  DOI：

  10.1055/s-0035-1561317
• 作为产物：
  描述：

  大茴香酸 在 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 2,6-bis(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole
  参考文献：
  名称：

  2,6-Disubstituted imidazo[2,1-b][1,3,4]thiadiazoles: Search for anticancer agents

  摘要：

  In this study, some novel 2,6-disubstituted imidazo[2,1-b][1,3,4]thiadiazoles 4 (a-i), 7 (a-p) and 11 (a-i) were synthesized from 5-substituted-1,3,4-thiadiazol-2-amine. The newly synthesized compounds 4a, 4b, 4c, 4e, 4g, 7j, 7l, 11b and 11c were evaluated in the National Cancer Institute for single dose in vitro primary cytotoxicity assay. Among the tested nine compounds, compound 4b (107166/760239) and 4c (107168/760240) were passed the criteria for activity in this assay and scheduled automatically for evaluation against the full panel of 60 human tumor cell lines at a minimum of five concentrations at 10-fold dilutions. 3-(2-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)aniline (4c) exhibited significant in vitro anticancer activity against Non Small Cell Lung Cancer HOP-92 cell line (GI(50): 0.114 mu M) and Renal Cancer CAKI-1 cell line (GI(50): 0.743 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.012

文献信息

• Synthesis of 2,6-Disubstituted Imidazo[2,1-b][1,3,4]thiadiazoles through Cyclization and Suzuki-Miyaura Cross-Coupling Reactions
  作者：Chloé Copin、Nicolas Henry、Frédéric Buron、Sylvain Routier

  DOI：10.1002/ejoc.201200237

  日期：2012.6

  Highly substituted imidazo[2,1-b][1,3,4]thiadiazole derivatives were synthesized through successive cyclization and Suzuki–Miyaura cross-coupling reactions. The palladium-catalyzed coupling reaction was optimized and a wide range of boronic acids was used to evaluate the scope and limitations of the methodology. The final compounds were obtained in fair to very good yields and high compatibility with

  通过连续环化和 Suzuki-Miyaura 交叉偶联反应合成了高度取代的咪唑并 [2,1-b][1,3,4] 噻二唑衍生物。对钯催化的偶联反应进行了优化，并使用了多种硼酸来评估该方法的范围和局限性。最终化合物以一般到非常好的产率获得，并且观察到与各种化学功能或（杂）循环的高度相容性。
• Heterocycles 48. Synthesis, Characterization and Biological Evaluation of Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives as Anti-Inflammatory Agents
  作者：Anamaria Cristina、Denisa Leonte、Laurian Vlase、László Bencze、Silvia Imre、Gabriel Marc、Bogdan Apan、Cristina Mogoșan、Valentin Zaharia

  DOI：10.3390/molecules23102425

  日期：——

  cardiovascular risk and renal function abnormalities. In order to synthesize new anti-inflammatory and analgesic compounds with a safer profile of side effects, a series of 2,6-diaryl-imidazo[2,1-b][1,3,4]thiadiazole derivatives 5a⁻l were synthesized and evaluated in vivo for their anti-inflammatory and analgesic activities in carrageenan-induced rat paw edema. Among all compounds, 5c showed better anti-inflammatory

  非甾体抗炎药（NSAID）是一类重要的药理学药物，用于治疗炎症性疾病。它们还具有严重的副作用，例如胃肠道损伤、心血管风险增加和肾功能异常。为了合成副作用更安全的新型抗炎镇痛化合物，合成了一系列2,6-二芳基咪唑并[2,1-b][1,3,4]噻二唑衍生物5a⁻l并在体内评估了它们对角叉菜胶引起的大鼠爪水肿的抗炎和镇痛活性。在所有化合物中，与标准药物双氯芬酸相比，5c 显示出更好的抗炎活性，而化合物 5g、5i、5j 则表现出与双氯芬酸相当的抗伤害活性。这些化合物均未表现出致溃疡活性。进行了分子对接研究，以研究化合物与靶标环氧合酶 (COX-1/COX-2) 之间的理论键相互作用。与双氯芬酸相比，化合物5c表现出更高的COX-2抑制作用。
• 2,6-Disubstituted imidazo[2,1-b][1,3,4]thiadiazoles: Search for anticancer agents
  作者：Malleshappa N. Noolvi、Harun M. Patel、Sarita Kamboj、Amandeep Kaur、Vikas Mann

  DOI：10.1016/j.ejmech.2012.08.012

  日期：2012.10

  In this study, some novel 2,6-disubstituted imidazo[2,1-b][1,3,4]thiadiazoles 4 (a-i), 7 (a-p) and 11 (a-i) were synthesized from 5-substituted-1,3,4-thiadiazol-2-amine. The newly synthesized compounds 4a, 4b, 4c, 4e, 4g, 7j, 7l, 11b and 11c were evaluated in the National Cancer Institute for single dose in vitro primary cytotoxicity assay. Among the tested nine compounds, compound 4b (107166/760239) and 4c (107168/760240) were passed the criteria for activity in this assay and scheduled automatically for evaluation against the full panel of 60 human tumor cell lines at a minimum of five concentrations at 10-fold dilutions. 3-(2-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)aniline (4c) exhibited significant in vitro anticancer activity against Non Small Cell Lung Cancer HOP-92 cell line (GI(50): 0.114 mu M) and Renal Cancer CAKI-1 cell line (GI(50): 0.743 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.
• Palladium-Catalyzed Direct Arylation of 2,6-Disubstituted Imidazo[2,1-b][1,3,4]thiadiazoles
  作者：Sylvain Routier、Chloé Copin、Nicolas Henry、Frédéric Buron

  DOI：10.1055/s-0035-1561317

  日期：——

  a C–H arylation process. The scope of the reaction demonstrated the critical importance of the electronic effects of each substituent on the efficiency of the reaction. In addition, a double efficient ‘one-pot’ functionalization at the C-2 and then at the C-5 positions of 2-bromo-6-arylimidazo[2,1- b ][1,3,4]thiadiazole derivatives was achieved using a sequential Suzuki–Miyaura–C–H arylation cascade

  这项工作报告了使用 C–H 芳基化过程合成三芳基咪唑并 [2,1-b][1,3,4] 噻二唑衍生物的原始合成方法。反应范围证明了每个取代基的电子效应对反应效率的关键重要性。此外，在 2-溴-6-芳基咪唑 [2,1-b][1,3,4] 噻二唑衍生物的 C-2 和 C-5 位置进行了双重有效的“一锅法”功能化。使用顺序 Suzuki-Miyaura-C-H 芳基化级联程序实现。