4-羟基-15-三唑基取代异丙酸内酯衍生物的合成及细胞毒性研究

IF 0.9 4区化学 Q4 CHEMISTRY, MEDICINAL

Chemistry of Natural Compounds Pub Date : 2025-09-18 DOI:10.1007/s10600-025-04781-5

S. S. Patrushev, T. V. Rybalova, Yu. V. Meshkova, M. K. Marenina, T. G. Tolstikova, E. E. Shults

{"title":"4-羟基-15-三唑基取代异丙酸内酯衍生物的合成及细胞毒性研究","authors":"S. S. Patrushev, T. V. Rybalova, Yu. V. Meshkova, M. K. Marenina, T. G. Tolstikova, E. E. Shults","doi":"10.1007/s10600-025-04781-5","DOIUrl":null,"url":null,"abstract":"A method for modifying ring A of isoalantolactone to produce 4(R)-hydroxy-15-triazolyl derivatives was developed. The key steps in the transformation included sequential azidolysis of 13-methoxy-4,15-epoxy- 11,13-dihydroisoalantolactones and Cu-catalyzed azide-alkyne cycloaddition with various alkynes. A retro-Michael reaction of (11R)- and (11S)-stereoisomeric (4R)-hydroxy-13-methoxy-15-triazolyl-11,13- dihydroisoalantolactones using cesium carbonate in DMF formed isoalantolactone derivatives. The structures of three compounds were established by X-ray crystal structure analyses.","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":"61 5","pages":"888 - 899"},"PeriodicalIF":0.9000,"publicationDate":"2025-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis and Cytotoxicity of 4-Hydroxy-15-Triazolyl-Substituted Isoalantolactone Derivatives\",\"authors\":\"S. S. Patrushev, T. V. Rybalova, Yu. V. Meshkova, M. K. Marenina, T. G. Tolstikova, E. E. Shults\",\"doi\":\"10.1007/s10600-025-04781-5\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A method for modifying ring A of isoalantolactone to produce 4(R)-hydroxy-15-triazolyl derivatives was developed. The key steps in the transformation included sequential azidolysis of 13-methoxy-4,15-epoxy- 11,13-dihydroisoalantolactones and Cu-catalyzed azide-alkyne cycloaddition with various alkynes. A retro-Michael reaction of (11R)- and (11S)-stereoisomeric (4R)-hydroxy-13-methoxy-15-triazolyl-11,13- dihydroisoalantolactones using cesium carbonate in DMF formed isoalantolactone derivatives. The structures of three compounds were established by X-ray crystal structure analyses.\",\"PeriodicalId\":514,\"journal\":{\"name\":\"Chemistry of Natural Compounds\",\"volume\":\"61 5\",\"pages\":\"888 - 899\"},\"PeriodicalIF\":0.9000,\"publicationDate\":\"2025-09-18\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemistry of Natural Compounds\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s10600-025-04781-5\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry of Natural Compounds","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s10600-025-04781-5","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}

引用次数: 0

摘要

研究了异丙酸内酯A环改性制备4(R)-羟基-15-三唑基衍生物的方法。转化的关键步骤包括13-甲氧基-4,15-环氧- 1,13-二氢异丙酸内酯的序贯叠氮化分解和铜催化叠氮化炔烃与各种炔烃的环加成。（11R）-和(11S)-立体异构体(4R)-羟基-13-甲氧基-15-三唑基-11,13-二氢异丙酸内酯用碳酸铯在DMF中进行反迈克尔反应生成异丙酸内酯衍生物。通过x射线晶体结构分析确定了三种化合物的结构。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synthesis and Cytotoxicity of 4-Hydroxy-15-Triazolyl-Substituted Isoalantolactone Derivatives

查看原文本刊更多论文

Synthesis and Cytotoxicity of 4-Hydroxy-15-Triazolyl-Substituted Isoalantolactone Derivatives

A method for modifying ring A of isoalantolactone to produce 4(R)-hydroxy-15-triazolyl derivatives was developed. The key steps in the transformation included sequential azidolysis of 13-methoxy-4,15-epoxy- 11,13-dihydroisoalantolactones and Cu-catalyzed azide-alkyne cycloaddition with various alkynes. A retro-Michael reaction of (11R)- and (11S)-stereoisomeric (4R)-hydroxy-13-methoxy-15-triazolyl-11,13- dihydroisoalantolactones using cesium carbonate in DMF formed isoalantolactone derivatives. The structures of three compounds were established by X-ray crystal structure analyses.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Chemistry of Natural Compounds 化学-有机化学

CiteScore

1.40

自引率

25.00%

发文量

265

审稿时长

7.8 months

期刊介绍： Chemistry of Natural Compounds publishes reviews and general articles about the structure of different classes of natural compounds, the chemical characteristics of botanical families, genus, and species, to establish the comparative laws and connection between physiological activity and the structure of substances.