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Synthesis of chalcone precursor via Cu(I) catalyzed 1,3‐dipolar reaction of functionalized acetylene and pyrazole embedded dipole
Journal of Heterocyclic Chemistry ( IF 2.4 ) Pub Date : 2020-07-01 , DOI: 10.1002/jhet.4083
Manju Nagaraja 1 , Balakrishna Kalluraya 1 , Asma 1 , Tharangini K. Shreekanth 1 , Madan S. Kumar 2
Affiliation  

A new class of functionalized pyrazole bearing 1,2,3‐triazole has been synthesized via Cu(I) mediated 1,3‐dipolar cycloaddition of pyrazole bearing azide with various aromatic/heteroaromatic bearing terminal dipolarophile (acetylene). Structures of the newly synthesized compounds were explicated by analytical and spectral analysis. All the newly synthesized compounds were evaluated for their in‐vitro antibacterial and antioxidant activity. Among the synthesized compound, triazole bearing 2,5‐thiazolidinone 5b (20 ± 0.70) and triazole bearing thiocarboamide 5e (19 ± 0.70) showed good antibacterial activity against Escherichia coli and Pseudomonas aeruginosa, respectively. The newly synthesized compounds further tested for their ability to bleach DPPH radical using DPPH scavenging assay. Among the synthesized compounds 1,2,3‐triazole bearing 2,5‐thiazolidinone 5b (58.81%) exhibited good DPPH scavenging activity compared to the rest of the compounds. From the X‐ray and Hirshfield analysis, it was observed that compound 3, crystallizes in a triclinic crystal system with a P‐1 space group. The major intercontacts present in these molecules are H…H (39.7%), C…H (23.9%), N…H (20.3%).

中文翻译:

铜(I)催化查尔酮前体的合成催化功能化乙炔和吡唑嵌入偶极的1,3-偶极反应

通过Cu(I)介导的吡唑叠氮化物与各种芳香族/杂芳族轴承端双极性亲子基团(乙炔)介导的1,3-偶极环加成反应合成了一类新型的带有1,2,3-三唑的功能化吡唑。通过分析和光谱分析阐明了新合成的化合物的结构。对所有新合成的化合物的体外抗菌和抗氧化活性进行了评估。在合成的化合物中,带有2,5-噻唑烷酮5b(20±0.70)的三唑和带有thiocarboamide 5e(19±0.70)的三唑对大肠杆菌铜绿假单胞菌具有良好的抗菌活性。, 分别。新合成的化合物使用DPPH清除试验进一步测试了漂白DPPH自由基的能力。在合成的1,2,3-三唑中,带有2,5-噻唑烷酮5b(58.81%)的DPPH清除活性优于其余化合物。通过X射线和Hirshfield分析,可以观察到化合物3在具有P-1空间群的三斜晶系​​晶体中结晶。这些分子中存在的主要相互接触是H…H(39.7%),C…H(23.9%),N…H(20.3%)。
更新日期:2020-07-01
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