s -氨基磺酰胺中S-N键的还原断裂

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-04-25 DOI:10.1021/acs.joc.4c02898

Qi Hou, Zhijun Yuan, Yaoping Ruan, Bohong Lin, Jianming Liang, Jing Zhang

{"title":"s -氨基磺酰胺中S-N键的还原断裂","authors":"Qi Hou, Zhijun Yuan, Yaoping Ruan, Bohong Lin, Jianming Liang, Jing Zhang","doi":"10.1021/acs.joc.4c02898","DOIUrl":null,"url":null,"abstract":"In this study, reductive breakage of the S–N bond on <i>S</i>-amidino sulfenamides was examined to explore prodrug or covalent drug chemistry for thiourea compounds. Upon thiol treatment, efficient release of varying thioureas could be reached, with Pd catalysis further accelerating this process. Preliminary application to antithyroid drug methylthiouracil confirmed cysteine-triggered release of the parent drug, although further development was hampered by stability issues. These findings highlight the potential of tunable sulfenamide prodrugs to balance release kinetics and stability for thiourea therapeutics.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"14 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Reductive Breakage of the S–N Bond in S-Amidino Sulfenamides\",\"authors\":\"Qi Hou, Zhijun Yuan, Yaoping Ruan, Bohong Lin, Jianming Liang, Jing Zhang\",\"doi\":\"10.1021/acs.joc.4c02898\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"In this study, reductive breakage of the S–N bond on <i>S</i>-amidino sulfenamides was examined to explore prodrug or covalent drug chemistry for thiourea compounds. Upon thiol treatment, efficient release of varying thioureas could be reached, with Pd catalysis further accelerating this process. Preliminary application to antithyroid drug methylthiouracil confirmed cysteine-triggered release of the parent drug, although further development was hampered by stability issues. These findings highlight the potential of tunable sulfenamide prodrugs to balance release kinetics and stability for thiourea therapeutics.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"14 1\",\"pages\":\"\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2025-04-25\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.joc.4c02898\",\"RegionNum\":2,\"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":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c02898","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

在本研究中，研究了s -氨基磺酰胺上S-N键的还原性断裂，以探索硫脲化合物的前药或共价药物化学。经硫醇处理后，各种硫脲的有效释放可以达到，而Pd的催化作用进一步加速了这一过程。抗甲状腺药物甲基硫脲嘧啶的初步应用证实了半胱氨酸引发的母体药物释放，尽管进一步的开发受到稳定性问题的阻碍。这些发现强调了可调亚胺前药平衡硫脲治疗药物释放动力学和稳定性的潜力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Reductive Breakage of the S–N Bond in S-Amidino Sulfenamides

查看原文本刊更多论文

Reductive Breakage of the S–N Bond in S-Amidino Sulfenamides

In this study, reductive breakage of the S–N bond on S-amidino sulfenamides was examined to explore prodrug or covalent drug chemistry for thiourea compounds. Upon thiol treatment, efficient release of varying thioureas could be reached, with Pd catalysis further accelerating this process. Preliminary application to antithyroid drug methylthiouracil confirmed cysteine-triggered release of the parent drug, although further development was hampered by stability issues. These findings highlight the potential of tunable sulfenamide prodrugs to balance release kinetics and stability for thiourea therapeutics.

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

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.