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Application of PEG400 in the one-pot synthesis of 7-[4-alkyl- or (hetero)aryl-1H-1,2,3-triazol-1-yl]thieno[3,2-b]pyridines via SNAr and Cu(I)-Catalyzed Azide-Alkyne Cycloaddition and preliminary evaluation of their anti-tumour activity
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2020-04-02 , DOI: 10.1016/j.tetlet.2020.151900
Juliana M. Rodrigues , Ricardo C. Calhelha , Isabel C.F.R. Ferreira , Maria-João R.P. Queiroz

Several novel 7-[4-alkyl- or (hetero)aryl-1H-1,2,3-triazol-1-yl]thieno[3,2-b]pyridines were prepared in good to high yields, using the environmentally friendly solvent PEG400 in a one-pot procedure from 7-chlorothieno[3,2-b]pyridine to form the corresponding azide via SNAr with NaN3, followed by Cu(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC) using different types of alkynes. This one-pot reaction in PEG400 starting from a halogenated heteroaromatic system is reported for the first time and demonstrated a wide scope of application for alkynes. Preliminary anti-tumour activity on human tumour cell lines using the prepared 1,4-di(hetero)aryl-1,2,3-triazoles was evaluated, together with their toxicity in non-tumour cells. Among the tested compounds the most promising one was a 2-ethynylpyridine derivative.



中文翻译:

PEG 400通过S一锅合成7- [4-烷基-或(杂)芳基-1 H -1,2,3-三唑-1-基]噻吩并[3,2- b ]吡啶中的应用N Ar和Cu(I)催化的叠氮化物-炔烃环加成反应及其抗肿瘤活性的初步评估

几种新型的7- [4-烷基-或(杂)芳基-1 H -1,2,3-三唑-1-基]噻吩并[3,2- b ]吡啶是采用环保方法制备的。型溶剂PEG 400从7-氯噻吩并[3,2-一个一锅法中b ]吡啶以形成相应的叠氮化物通过小号ñ的Ar与NaN的3,随后的Cu(I)催化的叠氮化物-炔烃环加成加成(CuAAC)使用不同类型的炔烃 PEG 400中的一锅反应首次报道了从卤代杂芳族体系开始的炔烃,证明了其在炔烃中的广泛应用。使用制备的1,4-二(杂)芳基-1,2,3-三唑对人类肿瘤细胞系的初步抗肿瘤活性及其在非肿瘤细胞中的毒性进行了评估。在测试的化合物中,最有希望的化合物是2-乙炔基吡啶衍生物。

更新日期:2020-04-02
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