{"title":"Synthesis and biological properties of stable phosmidosine analogs.","authors":"Kazuhisa Okada, Haruhiko Taguchi, Kohji Seio, Hideaki Kakeya, Hiroyuki Osada, Takuma Sasaki, Mitsuo Sekine","doi":"10.1093/nass/3.1.105","DOIUrl":null,"url":null,"abstract":"<p><p>Phosmidosine and a variety of its analogs were synthesized by reaction of N-diisopropyl-N'-(N tritylaminoacyl)phosphorodiamidite derivatives with appropriately protected 8-oxoadenosine derivatives. It was found that replacement of the methyl group of the N-acylphosphoramidate linkage with longer alkyl groups resulted in significant stabilization of the ester linkage. Among the phosmidosine analogs synthesized, the O-ethyl derivative was easily synthesized and was found to be sufficiently stable under acidic and neutral conditions. These stable phosmidosine analogs exhibited similar antitumor activities against several cancer cell lines. The structure-activity relationship is also discussed.</p>","PeriodicalId":86149,"journal":{"name":"Nucleic acids research. Supplement (2001)","volume":" 3","pages":"105-6"},"PeriodicalIF":0.0000,"publicationDate":"2003-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1093/nass/3.1.105","citationCount":"1","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Nucleic acids research. Supplement (2001)","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1093/nass/3.1.105","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 1
Abstract
Phosmidosine and a variety of its analogs were synthesized by reaction of N-diisopropyl-N'-(N tritylaminoacyl)phosphorodiamidite derivatives with appropriately protected 8-oxoadenosine derivatives. It was found that replacement of the methyl group of the N-acylphosphoramidate linkage with longer alkyl groups resulted in significant stabilization of the ester linkage. Among the phosmidosine analogs synthesized, the O-ethyl derivative was easily synthesized and was found to be sufficiently stable under acidic and neutral conditions. These stable phosmidosine analogs exhibited similar antitumor activities against several cancer cell lines. The structure-activity relationship is also discussed.
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