Daniel A. McNaughton , Edward York , Tristan Rawling , Philip A. Gale
{"title":"将 N,N'-二甲基水酰胺作为阴离子团设计的核心支架。","authors":"Daniel A. McNaughton , Edward York , Tristan Rawling , Philip A. Gale","doi":"10.1039/d4ob00703d","DOIUrl":null,"url":null,"abstract":"<div><p>The <em>N</em>,<em>N</em>′-dimethylation of a diphenylsquaramide induces a conformational change in the orientation of the phenyl rings. This has been exploited to create a series of bis-urea, -thiourea and -squaramide anionophores. The compounds were shown to bind to Cl<sup>−</sup> using proton NMR titration techniques and to transport H<sup>+</sup>/Cl<sup>−</sup> through the lipid bilayers, whereas a non-methylated analogue displayed limited transport activity. Despite their potency in transport studies, the series had a negligible impact on cancer cell viability.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"N,N′-Dimethylsquaramide as a central scaffold for anionophore design†\",\"authors\":\"Daniel A. McNaughton , Edward York , Tristan Rawling , Philip A. Gale\",\"doi\":\"10.1039/d4ob00703d\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>The <em>N</em>,<em>N</em>′-dimethylation of a diphenylsquaramide induces a conformational change in the orientation of the phenyl rings. This has been exploited to create a series of bis-urea, -thiourea and -squaramide anionophores. The compounds were shown to bind to Cl<sup>−</sup> using proton NMR titration techniques and to transport H<sup>+</sup>/Cl<sup>−</sup> through the lipid bilayers, whereas a non-methylated analogue displayed limited transport activity. Despite their potency in transport studies, the series had a negligible impact on cancer cell viability.</p></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.9000,\"publicationDate\":\"2024-06-19\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052024004907\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052024004907","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
N,N′-Dimethylsquaramide as a central scaffold for anionophore design†
The N,N′-dimethylation of a diphenylsquaramide induces a conformational change in the orientation of the phenyl rings. This has been exploited to create a series of bis-urea, -thiourea and -squaramide anionophores. The compounds were shown to bind to Cl− using proton NMR titration techniques and to transport H+/Cl− through the lipid bilayers, whereas a non-methylated analogue displayed limited transport activity. Despite their potency in transport studies, the series had a negligible impact on cancer cell viability.