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Stereoselective Synthesis of Biologically Relevant Heterocycles via Brønsted Acid Catalysis

通过布伦斯台德酸催化立体选择性合成生物相关杂环

基本信息

批准号：
10202815
负责人：
Kimberly Sue Petersen
金额：
$ 39.6万
依托单位：
UNIVERSITY OF NORTH CAROLINA GREENSBORO
依托单位国家：
美国
项目类别：
财政年份：
2021
资助国家：
美国
起止时间：
2021-06-01 至 2024-05-31
项目状态：
已结题

来源：
https://reporter.nih.gov/project-details/10202815
关键词：
3-Dimensional Achievement Acids Amino Acids Biochemistry Biological Carbon Catalysis Chemistry Communities Complex Cyclization Data Development Esters Evaluation FDA approved Funding Geometry Goals Handedness Indoles Institution Investigation Laboratory Research Lactams Lactones Lead Mentors Methodology Methods Natural Products Nature Nitriles Nitrogen North Carolina Pattern Periodicity Pharmaceutical Chemistry Pharmaceutical Preparations Phosphoric Acids Preparation Process Publications Reaction Research Research Personnel Science Shapes Structure Students System Underrepresented Populations Underrepresented Students United States National Institutes of Health Universities Work base beta-Lactams career enantiomer experience innovation insight novel novel strategies rapid technique small molecule symposium undergraduate research experience undergraduate student

项目摘要

PROJECT SUMMARY The goal of this proposal is to generate innovative strategies for the asymmetric preparation of different heterocyclic motifs, including N-containing compounds, that contain a chiral center. Realization of this goal is expected to benefit medicinal chemistry campaigns because >59% of FDA approved drugs include a nitrogen- containing ring system and >56% of FDA approved drugs contain a stereogenic center, the absolute configuration of which is often critical to the activity of the molecule. To induce asymmetry in the proposed processes, a Brønsted acid will be used to catalyze a stereoselective cyclization reaction, with a focus on the use of commercially available chiral phosphoric acids. We hypothesize that the chiral phosphoric acid will complex with the starting hydroxy and amino esters and nitriles to initiate a cyclization reaction that preferentially generates one product enantiomer over the other. Our methods rapidly build complex molecules under mild conditions, and our research will result in a significant advance over current state of the art. Preliminary results support the validity of our approach and we will offer insight into the potential uses of the generated products. The ring structures we will prepare are ideal candidates for further manipulation into other biologically relevant structures or for diversification and evaluation themselves. Notably, these investigations will be advanced primarily by M.S. and undergraduate student researchers.

项目总结