N-tert-butyl-6-phenylimidazo[2,1-b]thiazol-5-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-tert-butyl-6-phenylimidazo[2,1-b]thiazol-5-amine
• 英文别名: N-tert-butyl-6-phenylimidazo[2,1-b][1,3]thiazol-5-amine
• 化学式: C₁₅H₁₇N₃S
• 分子量: 271.386
• InChiKey: FJJLDWHAPOGRBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基噻唑 、 异氰酸叔丁酯 、 苯甲醛 在 1-butylsulfonic-3-methylimidazolium trifluoromethanesulfonate 作用下， 以 乙醇 为溶剂， 以62%的产率得到N-tert-butyl-6-phenylimidazo[2,1-b]thiazol-5-amine
  参考文献：
  名称：

  可重复使用的 Brønsted-酸性离子液体催化的 Groebke-Blackburn-Bienaymé 多组分反应

  摘要：

  Brønsted 酸性离子液体可有效催化 Groebke-Blackburn-Bienaymé 多组分反应合成咪唑并[1,2- a ]吡啶和咪唑并[ 2,1- b ]噻唑，产率适中（42-93%） ，在热或微波加热下。均相酸性催化剂可以在四个连续的反应循环中回收和重复使用。

  DOI：

  10.1002/ejoc.202200615

文献信息

• Bicyclic imidazo-5-yl-amine derivatives
  申请人：——

  公开号：US20020183320A1

  公开（公告）日：2002-12-05

  A novel bicyclic imidazo-5-yl-amine derivative of Formula I, 1 wherein X denotes CR 5 , N or S, and Y in the case where X denotes S, denotes CR 6 or N and in all other cases denotes N, and methods for preparation thereof are disclosed. Also disclosed are methods for treating pain using the compound of Formula I, and pharmaceutical compositions comprising the compound of Formula I.

  公开了一种新型的Formula I的双环咪唑-5-基胺衍生物，其中X表示CR5、N或S，当X表示S时，Y表示CR6或N，在所有其他情况下表示N，并公开了其制备方法。还公开了使用Formula I化合物治疗疼痛的方法，以及包含Formula I化合物的药物组合物。
• A sustainable and scalable multicomponent continuous flow process to access fused imidazoheterocycle pharmacophores
  作者：Blake J. M. Baker、William J. Kerr、David M. Lindsay、Vipulkumar K. Patel、Darren L. Poole

  DOI：10.1039/d0gc03675g

  日期：——

  A sustainable flow process has been established for the application of the Gröebke–Blackburn–Bienaymé reaction for access to high-value fused heteroaromatics.

  已建立了可持续的流程，用于应用Gröebke-Blackburn-Bienaymé反应，以获得高价值的融合杂环化合物。
• Groebke‐Blackburn‐Bienaymé Multicomponent Reaction Catalysed by Reusable Brønsted‐Acidic Ionic Liquids
  作者：Nicolas S. Anjos、Agáta I. Chapina、Ana R. Santos、Peter Licence、Luiz S. Longo

  DOI：10.1002/ejoc.202200615

  日期：2022.10.26

  Groebke-Blackburn-Bienaymé multicomponent reactions can be efficiently catalysed by Brønsted acidic ionic liquids for the synthesis of imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles in moderate to excellent yields (42–93 %), either under thermal or microwave heating. The homogeneous acidic catalyst can be recycled and reused in four consecutive reaction cycles.

  Brønsted 酸性离子液体可有效催化 Groebke-Blackburn-Bienaymé 多组分反应合成咪唑并[1,2- a ]吡啶和咪唑并[ 2,1- b ]噻唑，产率适中（42-93%） ，在热或微波加热下。均相酸性催化剂可以在四个连续的反应循环中回收和重复使用。
• A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating
  作者：Gabriela Santos、Nicolas Anjos、Miguel Gibeli、Guilherme Silva、Pâmela Fernandes、Everton Fiorentino、Luiz Longo Jr.

  DOI：10.21577/0103-5053.20200028

  日期：——

  Over the last twenty years. the Groebke-Blackburn-Bienayme (GBB) reaction has been emerged as a powerful tool to access different nitrogen-based heterocycles as privileged scaffolds in medicinal chemistry. This multicomponent reaction is usually catalyzed by ordinary Bronsted or Lewis acid catalysts. Herein, we present a comparative study on the catalytic efficiencies of different rare earth triflates in GBB reactions under microwave heating, involving 2-aminopyridine or 2-aminothiazole, as aminoazole component, and different aldehydes and aliphatic isocyanides. The use of gadolinium(III) triflate as cheaper alternative catalyst for the most commonly used scandium(III) titillate was acknowledged for the first time, and a library of twenty three imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles could be obtained in good to excellent yields.
• Design, synthesis and anticancer activity of 2-arylimidazo[1,2-a]pyridinyl-3-amines
  作者：Umesh Prasad Yadav、Arshad J. Ansari、Sahil Arora、Gaurav Joshi、Tashvinder Singh、Harsimrat Kaur、Nilambra Dogra、Raj Kumar、Santosh Kumar、Devesh M. Sawant、Sandeep Singh

  DOI：10.1016/j.bioorg.2021.105464

  日期：2022.1

  A series of imido-heterocycle compounds were designed, synthesized, characterized, and evaluated for the anticancer potential using breast (MCF-7 and MDA-MB-231), pancreatic (PANC-1), and colon (HCT-116 and HT-29) cancer cell lines and normal cells, while normal cells showed no toxicity. Among the screened compounds, 4h exhibited the best anticancer potential with IC50 values ranging from 1 to 5.5 μM. Compound 4h caused G2/M phase arrest and apoptosis in all the cell lines except MDA-MB-231 mammosphere formation was inhibited. In-vitro enzyme assay showed selective topoisomerase IIα inhibition by compound 4h, leading to DNA damage as observed by fluorescent staining. Cell signalling studies showed decreased expression of cell cycle promoting related proteins while apoptotic proteins were upregulated. Interestingly MDA-MB-231 cells showed only cytostatic effects upon treatment with compound 4h due to defective p53 status. Toxicity study using overexpression of dominant-negative mutant p53 in MCF-7 cells (which have wild type functional p53) showed that anticancer potential of compound 4h is positively correlated with p53 expression.