2-methyl-6-(4-nitrophenyl)imidazo[2,1-b][1,3,4]thiadiazole | 38107-62-9

• 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-methyl-6-(4-nitrophenyl)imidazo[2,1-b][1,3,4]thiadiazole
• 英文别名: 2-methyl-6-(4-nitro-phenyl)-imidazo[2,1-b][1,3,4]thiadiazole；2-Methyl-6-(4-nitro-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol
• CAS: 38107-62-9
• 化学式: C₁₁H₈N₄O₂S
• 分子量: 260.276
• InChiKey: TYEGAOHVZVVLIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methyl-6-(4-nitrophenyl)imidazo[2,1-b][1,3,4]thiadiazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以89%的产率得到2-methyl-5-bromo-6-(4-nitrophenyl)imidazo[2,1-b][1,3,4]thiadiazole
  参考文献：
  名称：

  C-5溴咪唑并[2,1-b][1,3,4]噻二唑的钯催化胺化

  摘要：

  报道了一种新的高效钯催化的咪唑并 [2,1-b][1,3,4] 噻二唑在微波辐射下的 C-5 位胺化。研究了 C-5 位溴释放的反应性，并优化了钯催化的交叉偶联条件。使用多种胺来检查该方法的范围和局限性。为了完成这项方法学研究，研究了额外的咪唑并 [2,1-b][1,3,4] 噻二唑取代的性质和位置的影响。

  DOI：

  10.1002/ejoc.201600145
• 作为产物：
  描述：

  2-(2-imino-5-methyl-[1,3,4]thiadiazol-3-yl)-1-(4-nitro-phenyl)-ethanone 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-methyl-6-(4-nitrophenyl)imidazo[2,1-b][1,3,4]thiadiazole
  参考文献：
  名称：

  Pentimalli,L. et al., Gazzetta Chimica Italiana, 1975, vol. 105, p. 777 - 787

  摘要：

  DOI：

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。
• Synthesis of 2,6-Disubstituted Imidazo[2,1-<i>b</i>][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.201201285

  日期：2012.12

  No abstract is available for this article.

  本文没有摘要。
• Identification of a novel BCL2-specific inhibitor that binds predominantly to the BH1 domain
  作者：Divyaanka Iyer、Supriya V. Vartak、Archita Mishra、Gunaseelan Goldsmith、Sujeet Kumar、Mrinal Srivastava、Mahesh Hegde、Vidya Gopalakrishnan、Mark Glenn、Mahesh Velusamy、Bibha Choudhary、Nagesh Kalakonda、Subhas S. Karki、Avadhesha Surolia、Sathees C. Raghavan

  DOI：10.1111/febs.13815

  日期：2016.9

  The antiapoptotic protein BCL2 is overexpressed in several cancers and contributes to prolonged cell survival and chemoresistance, lending itself as an excellent target for cancer therapy. Here, we report the design, synthesis, and characterization of Disarib, a novel BCL2 inhibitor. Disarib showed selective cytotoxicity in BCL2 high cancer cell lines, and CLL patient primary cells, as compared to BCL2 low cell lines. BCL2 knockdown in cells rendered remarkable resistance to Disarib, while sensitivity was regained upon its ectopic expression, establishing target specificity. In silico, biochemical and biophysical studies demonstrated strong affinity of Disarib to BCL2, but not to other antiapoptotic BCL2 family members viz., BCL‐xL, BCL2A1 etc. Interestingly, biophysical studies showed that BH1 domain deletion mutant demonstrated ~ 67‐fold reduction in BCL2‐Disarib interaction, while it was only ~ 20‐fold in the case of BH3 deletion mutant, suggesting predominant involvement of the BH1 domain for Disarib binding. Thus, we report identification of a novel BCL2 inhibitor with a unique mechanism of BCL2 inhibition, as opposed to the well‐studied BH3 domain targeting.
• Pentimalli,L. et al., Gazzetta Chimica Italiana, 1975, vol. 105, p. 777 - 787
  作者：Pentimalli,L. et al.

  DOI：——

  日期：——
• Palladium-Catalyzed Amination of C-5 Bromoimidazo[2,1-<i>b</i>]­[1,3,4]­thiadiazoles
  作者：Chloé Copin、Frédéric Buron、Sylvain Routier

  DOI：10.1002/ejoc.201600145

  日期：2016.4

  A new and efficient palladium-catalyzed amination of imidazo[2,1-b][1,3,4]thiadiazole at the C-5 position under microwave irradiation is reported. The reactivity toward bromine release at the C-5 position was investigated, and palladium-catalyzed cross-coupling conditions were optimized. A wide range of amines was employed to examine the scope and limitations of the method. To complete this methodological

  报道了一种新的高效钯催化的咪唑并 [2,1-b][1,3,4] 噻二唑在微波辐射下的 C-5 位胺化。研究了 C-5 位溴释放的反应性，并优化了钯催化的交叉偶联条件。使用多种胺来检查该方法的范围和局限性。为了完成这项方法学研究，研究了额外的咪唑并 [2,1-b][1,3,4] 噻二唑取代的性质和位置的影响。