Suppr超能文献

锂催化硫醇与叔醇和仲醇的烷基化反应:3-硫杂环丁烷作为生物电子等排体的合成

Lithium-Catalyzed Thiol Alkylation with Tertiary and Secondary Alcohols: Synthesis of 3-Sulfanyl-Oxetanes as Bioisosteres.

作者信息

Croft Rosemary A, Mousseau James J, Choi Chulho, Bull James A

机构信息

Department of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ, UK.

Pfizer Medicine Design, Eastern Point Road, Groton, CT, 06340, USA.

出版信息

Chemistry. 2018 Jan 19;24(4):818-821. doi: 10.1002/chem.201705576. Epub 2017 Dec 20.

Abstract

3-Sulfanyl-oxetanes are presented as promising novel bioisosteric replacements for thioesters or benzyl sulfides. From oxetan-3-ols, a mild and inexpensive Li catalyst enables chemoselective C-OH activation and thiol alkylation. Oxetane sulfides are formed from various thiols providing novel motifs in new chemical space and specifically as bioisosteres for thioesters due to their similar shape and electronic properties. Under the same conditions, various π-activated secondary and tertiary alcohols are also successful. Derivatization of the oxetane sulfide linker provides further novel oxetane classes and building blocks. Comparisons of key physicochemical properties of the oxetane compounds to selected carbonyl and methylene analogues indicate that these motifs are suitable for incorporation into drug discovery efforts.

摘要

3-硫烷基氧杂环丁烷被视为硫酯或苄基硫醚有前景的新型生物电子等排体替代物。从3-氧杂环丁醇出发,一种温和且廉价的锂催化剂能够实现化学选择性的C-OH活化和硫醇烷基化。氧杂环丁烷硫醚由各种硫醇形成,在新的化学空间中提供了新的结构单元,特别是作为硫酯的生物电子等排体,因为它们具有相似的形状和电子性质。在相同条件下,各种π-活化的仲醇和叔醇也能成功反应。氧杂环丁烷硫醚连接基的衍生化提供了更多新型的氧杂环丁烷类别和结构单元。将氧杂环丁烷化合物的关键物理化学性质与选定的羰基和亚甲基类似物进行比较表明,这些结构单元适合纳入药物研发工作中。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a299/5814735/f2c6c0e8926b/CHEM-24-818-g001.jpg

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验