Zijian Li , Yanle Men , Suhua Gao , Peipei Cui , Hongying Wang , Baoquan Chen
{"title":"含有 1,3,4-oxadiazole 和 1,2,4-riazole 硫醚分子的新型喹唑啉酮的设计、合成和抗增殖研究","authors":"Zijian Li , Yanle Men , Suhua Gao , Peipei Cui , Hongying Wang , Baoquan Chen","doi":"10.1080/10426507.2023.2245529","DOIUrl":null,"url":null,"abstract":"<div><p>In the current study, a series of 1,3,4-oxadiazole and 1,2,4-triazole derivatives linked to quinazolinone were designed and synthesized by using Phase Transfer Catalysis. The structures of the synthesized compounds were confirmed by their IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HR-ESI-MS spectroscopic data, and their <em>in vitro</em> antiproliferative activities against A549, Hela, MCF-7 as well as L929 were detected by using CCK-8 assay. The results demonstrated that most of the compounds showed better growth inhibitory effect than 5-FU on A549, Hela, and MCF-7 cell lines. Especially, 2-(5-((3-bromophenyl)thio)-1,3,4-oxadiazole-2-yl)quinazolin-4(3<em>H</em>)-one (<strong>8o</strong>), 4-amino-5-((4-nitrophenyl)thio)-4<em>H</em>-1,2,4-triazol-3-yl)quinazolin-4(3<em>H</em>)-one (<strong>9m</strong>) and 2-(4-amino-5-(<em>o</em>-tolylthio)-4<em>H</em>-1,2,4-triazol-3-yl)quinazolin-4(3<em>H</em>)-one (<strong>9b</strong>) showed good antiproliferative activity against A549 cells with IC<sub>50</sub> value of 3.46, 2.96, and 3.44 μM, respectively. 2-(4-Amino-5-((3,5-difluorophenyl)thio)-4<em>H</em>-1,2,4-triazol-3-yl)quinazolin-4(3<em>H</em>)-one (<strong>9h</strong>) and 4-amino-5-((4-nitrophenyl)thio)-4<em>H</em>-1,2,4-triazol-3-yl)quinazolin-4(3<em>H</em>)-one (<strong>9m</strong>) had obvious inhibitory effects on Hela cells with IC<sub>50</sub> values of 1.76 and 3.91 μM, respectively. 2-(4-Amino-5-((2-chlorophenyl)thio)-4<em>H</em>-1,2,4-triazol-3-yl)quinazolin-4(3<em>H</em>)-one (<strong>9i</strong>) showed high inhibitory activity against MCF-7 cells with IC<sub>50</sub> value of 2.72 μM. Meanwhile, all compounds showed lower cytotoxicity to L929 cells than positive control drug 5-FU. In development, according to the above preliminary observation, these novel quinazolinones incorporating 1,3,4-oxadiazole and 1,2,4-triazole thioether moieties could become potential molecular templates for searching new antitumor agents.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.4000,"publicationDate":"2024-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Design, synthesis, and antiproliferative investigation of novel quinazolinones incorporating 1,3,4-oxadiazole and 1,2,4-triazole thioether moieties\",\"authors\":\"Zijian Li , Yanle Men , Suhua Gao , Peipei Cui , Hongying Wang , Baoquan Chen\",\"doi\":\"10.1080/10426507.2023.2245529\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>In the current study, a series of 1,3,4-oxadiazole and 1,2,4-triazole derivatives linked to quinazolinone were designed and synthesized by using Phase Transfer Catalysis. The structures of the synthesized compounds were confirmed by their IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HR-ESI-MS spectroscopic data, and their <em>in vitro</em> antiproliferative activities against A549, Hela, MCF-7 as well as L929 were detected by using CCK-8 assay. The results demonstrated that most of the compounds showed better growth inhibitory effect than 5-FU on A549, Hela, and MCF-7 cell lines. Especially, 2-(5-((3-bromophenyl)thio)-1,3,4-oxadiazole-2-yl)quinazolin-4(3<em>H</em>)-one (<strong>8o</strong>), 4-amino-5-((4-nitrophenyl)thio)-4<em>H</em>-1,2,4-triazol-3-yl)quinazolin-4(3<em>H</em>)-one (<strong>9m</strong>) and 2-(4-amino-5-(<em>o</em>-tolylthio)-4<em>H</em>-1,2,4-triazol-3-yl)quinazolin-4(3<em>H</em>)-one (<strong>9b</strong>) showed good antiproliferative activity against A549 cells with IC<sub>50</sub> value of 3.46, 2.96, and 3.44 μM, respectively. 2-(4-Amino-5-((3,5-difluorophenyl)thio)-4<em>H</em>-1,2,4-triazol-3-yl)quinazolin-4(3<em>H</em>)-one (<strong>9h</strong>) and 4-amino-5-((4-nitrophenyl)thio)-4<em>H</em>-1,2,4-triazol-3-yl)quinazolin-4(3<em>H</em>)-one (<strong>9m</strong>) had obvious inhibitory effects on Hela cells with IC<sub>50</sub> values of 1.76 and 3.91 μM, respectively. 2-(4-Amino-5-((2-chlorophenyl)thio)-4<em>H</em>-1,2,4-triazol-3-yl)quinazolin-4(3<em>H</em>)-one (<strong>9i</strong>) showed high inhibitory activity against MCF-7 cells with IC<sub>50</sub> value of 2.72 μM. Meanwhile, all compounds showed lower cytotoxicity to L929 cells than positive control drug 5-FU. In development, according to the above preliminary observation, these novel quinazolinones incorporating 1,3,4-oxadiazole and 1,2,4-triazole thioether moieties could become potential molecular templates for searching new antitumor agents.</p></div>\",\"PeriodicalId\":20056,\"journal\":{\"name\":\"Phosphorus, Sulfur, and Silicon and the Related Elements\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.4000,\"publicationDate\":\"2024-01-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Phosphorus, Sulfur, and Silicon and the Related Elements\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1042650723002265\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, INORGANIC & NUCLEAR\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phosphorus, Sulfur, and Silicon and the Related Elements","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1042650723002265","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
Design, synthesis, and antiproliferative investigation of novel quinazolinones incorporating 1,3,4-oxadiazole and 1,2,4-triazole thioether moieties
In the current study, a series of 1,3,4-oxadiazole and 1,2,4-triazole derivatives linked to quinazolinone were designed and synthesized by using Phase Transfer Catalysis. The structures of the synthesized compounds were confirmed by their IR, 1H NMR, 13C NMR, and HR-ESI-MS spectroscopic data, and their in vitro antiproliferative activities against A549, Hela, MCF-7 as well as L929 were detected by using CCK-8 assay. The results demonstrated that most of the compounds showed better growth inhibitory effect than 5-FU on A549, Hela, and MCF-7 cell lines. Especially, 2-(5-((3-bromophenyl)thio)-1,3,4-oxadiazole-2-yl)quinazolin-4(3H)-one (8o), 4-amino-5-((4-nitrophenyl)thio)-4H-1,2,4-triazol-3-yl)quinazolin-4(3H)-one (9m) and 2-(4-amino-5-(o-tolylthio)-4H-1,2,4-triazol-3-yl)quinazolin-4(3H)-one (9b) showed good antiproliferative activity against A549 cells with IC50 value of 3.46, 2.96, and 3.44 μM, respectively. 2-(4-Amino-5-((3,5-difluorophenyl)thio)-4H-1,2,4-triazol-3-yl)quinazolin-4(3H)-one (9h) and 4-amino-5-((4-nitrophenyl)thio)-4H-1,2,4-triazol-3-yl)quinazolin-4(3H)-one (9m) had obvious inhibitory effects on Hela cells with IC50 values of 1.76 and 3.91 μM, respectively. 2-(4-Amino-5-((2-chlorophenyl)thio)-4H-1,2,4-triazol-3-yl)quinazolin-4(3H)-one (9i) showed high inhibitory activity against MCF-7 cells with IC50 value of 2.72 μM. Meanwhile, all compounds showed lower cytotoxicity to L929 cells than positive control drug 5-FU. In development, according to the above preliminary observation, these novel quinazolinones incorporating 1,3,4-oxadiazole and 1,2,4-triazole thioether moieties could become potential molecular templates for searching new antitumor agents.
期刊介绍:
Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.