{"title":"Catalyst-free one-pot three-component synthesis and in silico bioactivity of new 4-pyrazolyl pyrano[3,4-c] pyrrole derivatives","authors":"Brahim Cherfaoui, Houria Lakhdari, Norah Bennamane, Hocine Merazig, Ahmed Djafri, Abdelghani Bouchama, Bellara Nedjar-Kolli","doi":"10.1007/s13738-024-03125-4","DOIUrl":null,"url":null,"abstract":"<div><p>An unexpected route for the synthesis of pyrano [3,4-<i>c</i>] pyrrole derivatives has been reported via catalyst-free, three-component reaction of 1,3-dicarbonyl pyrazole, aromatic primary amines and fumaryl chloride. This novel cascade reaction sequence led to create two new rings and four new <i>σ</i> bonds containing two C–N, one C–C, and one C–O bond. The newly synthesized compounds were elucidated on the basis of their spectroscopic data (<sup>1</sup>H, <sup>13</sup>C, 2D NMR, HRMS, IR) and additionally confirmed by single-crystal X-ray diffraction analysis. The molecular docking simulation was performed utilizing the AutoDock 4.2 program to predict the binding affinity of one derivative of the synthesized compounds to the target mitogen-activated protein kinase P38 (MAPK P38) and mitogen-activated protein kinase 14 (MAPK 14).</p><h3>Graphical abstract</h3>\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":"21 12","pages":"2975 - 2982"},"PeriodicalIF":2.2000,"publicationDate":"2024-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the Iranian Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s13738-024-03125-4","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
An unexpected route for the synthesis of pyrano [3,4-c] pyrrole derivatives has been reported via catalyst-free, three-component reaction of 1,3-dicarbonyl pyrazole, aromatic primary amines and fumaryl chloride. This novel cascade reaction sequence led to create two new rings and four new σ bonds containing two C–N, one C–C, and one C–O bond. The newly synthesized compounds were elucidated on the basis of their spectroscopic data (1H, 13C, 2D NMR, HRMS, IR) and additionally confirmed by single-crystal X-ray diffraction analysis. The molecular docking simulation was performed utilizing the AutoDock 4.2 program to predict the binding affinity of one derivative of the synthesized compounds to the target mitogen-activated protein kinase P38 (MAPK P38) and mitogen-activated protein kinase 14 (MAPK 14).
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JICS is an international journal covering general fields of chemistry. JICS welcomes high quality original papers in English dealing with experimental, theoretical and applied research related to all branches of chemistry. These include the fields of analytical, inorganic, organic and physical chemistry as well as the chemical biology area. Review articles discussing specific areas of chemistry of current chemical or biological importance are also published. JICS ensures visibility of your research results to a worldwide audience in science. You are kindly invited to submit your manuscript to the Editor-in-Chief or Regional Editor. All contributions in the form of original papers or short communications will be peer reviewed and published free of charge after acceptance.
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