A one-pot route to novel 3-{1-([5-amino-7-(arylamino)-6-cyano-7H-[1,4]oxaphosphinino[2,3-d]thiazol-2-yl]hydrazinyl)ethylidene}-2H-chromen-2-one: Synthesis, cytotoxic activities, apoptosis, and cell cycle studies
Wafa A. Bawazir (Investigation Methodology) , Tarik E. Ali (Conceptualization Funding acquisition Supervision Writing – original draft Writing – review & editing) , Mohammed A. Assiri (Formal analysis Software) , Serag E. I. Elbehairi (Methodology Validation) , Mohamed Abdel-Megid (Visualization Writing – review & editing)
{"title":"A one-pot route to novel 3-{1-([5-amino-7-(arylamino)-6-cyano-7H-[1,4]oxaphosphinino[2,3-d]thiazol-2-yl]hydrazinyl)ethylidene}-2H-chromen-2-one: Synthesis, cytotoxic activities, apoptosis, and cell cycle studies","authors":"Wafa A. Bawazir (Investigation Methodology) , Tarik E. Ali (Conceptualization Funding acquisition Supervision Writing – original draft Writing – review & editing) , Mohammed A. Assiri (Formal analysis Software) , Serag E. I. Elbehairi (Methodology Validation) , Mohamed Abdel-Megid (Visualization Writing – review & editing)","doi":"10.1080/00397911.2025.2521830","DOIUrl":null,"url":null,"abstract":"<div><div>An innovative and efficient one-pot approach has been established for the synthesis of 3-{1-([5-amino-7-(arylamino)-6-cyano-7<em>H</em>-[1,4]oxaphosphinino[2,3-d]thiazol-2-yl]hydrazinyl)ethylidene}-2<em>H</em>-chromen-2-one (<strong>2a–h</strong>) using aromatic amine, phosphorus trichloride, malononitrile, and 3-{[1-(4-oxo-5<em>H</em>-thiazol-2-yl)hydrazinyl]ethylidene}-2<em>H</em>-chromen-2-one with triethylamine. This method is efficient and straightforward, offering high yields, easy product isolation, and minimal waste. The cytotoxic properties against PC3, LS174T, and HepG2 cancer cell lines revealed promising activity for compounds <strong>2d</strong> and <strong>2e</strong> (fluorine and chlorine substitutions), comparable to Tivozanib. Flow cytometry indicated that these bioactive compounds significantly increased late apoptosis and halted cell cycle progression at S and G2 phases, demonstrating their potential as anticancer agents. Both compounds <strong>2d</strong> and <strong>2e</strong> were then subjected to a molecular docking experiment to see how they bind with VEGFR-2 receptor.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 13","pages":"Pages 1007-1028"},"PeriodicalIF":1.8000,"publicationDate":"2025-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthetic Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0039791125000608","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
An innovative and efficient one-pot approach has been established for the synthesis of 3-{1-([5-amino-7-(arylamino)-6-cyano-7H-[1,4]oxaphosphinino[2,3-d]thiazol-2-yl]hydrazinyl)ethylidene}-2H-chromen-2-one (2a–h) using aromatic amine, phosphorus trichloride, malononitrile, and 3-{[1-(4-oxo-5H-thiazol-2-yl)hydrazinyl]ethylidene}-2H-chromen-2-one with triethylamine. This method is efficient and straightforward, offering high yields, easy product isolation, and minimal waste. The cytotoxic properties against PC3, LS174T, and HepG2 cancer cell lines revealed promising activity for compounds 2d and 2e (fluorine and chlorine substitutions), comparable to Tivozanib. Flow cytometry indicated that these bioactive compounds significantly increased late apoptosis and halted cell cycle progression at S and G2 phases, demonstrating their potential as anticancer agents. Both compounds 2d and 2e were then subjected to a molecular docking experiment to see how they bind with VEGFR-2 receptor.
期刊介绍:
Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.