氮杂环[1.1.0]丁基取代磺酰酰氟:亲电枢纽桥接晚期氮杂啶结合与硫代化学

IF 4 2区 化学 Q2 CHEMISTRY, APPLIED
Defne Serbetci , Philipp Natho , Ernesto Mesto , Emanuela Schingaro , Marco Colella , Renzo Luisi
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引用次数: 0

摘要

亲电应变小基序的发展对化学生物学和药物发现具有越来越重要的意义,可以实现精确的、后期的功能化和靶向共价抑制。在这项工作中,我们报道了一种新型的氮杂环[1.1.0]丁基取代磺酰咪甲酰氟的高效合成,这是一种结合了应变释放反应性和SuFEx化学性质的实验稳定的亲电枢纽。通过选择性ABB开环反应和SuFEx介导的与多种亲核试剂(包括药物相关衍生物)的连接,证明了该基序的双重反应性。进一步衍生化得到的磺胺酰亚胺和磺胺酰亚胺显示了该体系的合成通用性。这些发现为开发模块化、多功能的药物发现平台开辟了道路。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Azabicyclo[1.1.0]butyl‐Substituted Sulfonimidoyl Fluoride: Electrophilic Hub Bridging Late‐Stage Azetidine Incorporation with Sufex Chemistry
The development of electrophilic strained small motifs is of increasing importance for chemical biology and drug discovery, enabling precise, late‐stage functionalization and targeted covalent inhibition. In this work, we report the efficient synthesis of a novel azabicyclo[1.1.0]butyl‐substituted sulfonimidoyl fluoride, a bench‐stable electrophilic hub combining strain‐release reactivity and SuFEx chemistry. The dual reactivity of this motif was demonstrated through selective ABB ring‐opening reactions, and SuFEx‐mediated ligations with diverse nucleophiles, including pharmaceutically relevant derivatives. Further derivatization of the resulting sulfonimidates and sulfonimidamides showcased the synthetic versatility of this system. These findings open avenues for the development of modular, multifunctional platforms in drug discovery.
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来源期刊
Advanced Synthesis & Catalysis
Advanced Synthesis & Catalysis 化学-应用化学
CiteScore
9.40
自引率
7.40%
发文量
447
审稿时长
1.8 months
期刊介绍: Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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