CAREER: Efficient Synthesis of Biologically Relevant Cyclic and Polycyclic Terpenoid Compounds Using Alkyne Cyclizations

职业：利用炔环化有效合成生物学相关的环状和多环萜类化合物

• 批准号: 1555218
• 负责人: Wesley Chalifoux
• 金额: $ 65万
• 依托单位: Board of Regents, NSHE, obo University of Nevada, Reno
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2016
• 资助国家: 美国
• 起止时间: 2016-04-01 至 2022-03-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1555218&HistoricalAwards=false
• 关键词: CAREER; Efficient; Synthesis; Biologically; Relevant

With this CAREER Award, the Synthesis Program supports the research of Professor Wesley A. Chalifoux of the University of Nevada, Reno. Professor Chalifoux develops new chemical tools for the efficient synthesis of biologically active compounds. New methodology developed in this research focuses on the application of ynones for the efficient construction of complex cyclic compounds. Ynones are substances in which a carbon-carbon triple bond (an alkyne) is connected to a carbon oxygen double bond (a carbonyl group). This connection enhances chemical reactivity in bimolecular addition reactions. New strategies which are developed in this research have applications in the area of pharmaceutical synthesis and the field of medicine through the generation of biologically-relevant compound libraries. As the educational component of this project, Professor Chalifoux develops an outreach program that focuses on the mentoring of middle and high school students from low-income, first-generation college families as well as groups that are underrepresented in science. The project builds connections with middle and high schools located in the Reno, Nevada area. Visiting high school students work closely with graduate and undergraduate chemistry students in science-related activities associated with research projects within the Chalifoux group. In this project, cyclization and cycloaddition reactions of alkynes and alkynones are explored. This research develops an operationally simple synthetic methodology that converts readily available alkyne, diyne and diene starting materials into complex cyclic and polycyclic target molecules. Simple conjugated alkynes and more complex conjugated and cross-conjugated polyynes are explored as substrates for Diels-Alder cycloaddition reactions. These are further elaborated in multicomponent/tandem cyclization reactions that are designed to generate multiple new carbon-carbon bonds and rings in a single reaction step, with regio- and stereochemical control. This research has broad applications in the area of pharmaceutical synthesis and the field of medicine through the rapid generation of biologically relevant compound libraries. In addition to activities at the middle and high schools, the CAREER Award supports summer research activities at the University of Nevada. This improves recruitment of underrepresented students into Science, Technology, Engineering and Mathematical (STEM) careers and increases retention of students in the sciences.

有了这个职业奖，综合计划支持教授韦斯利A。来自里诺市内华达州大学的Chalifoux。Chalifoux教授开发了新的化学工具，用于有效合成生物活性化合物。本研究开发的新方法重点关注ynones在高效构建复杂环状化合物中的应用。 炔酮是其中碳-碳三键（炔）连接到碳氧双键（羰基）的物质。 这种连接增强了双分子加成反应中的化学反应性。在这项研究中开发的新策略通过生成生物相关化合物库在药物合成领域和医学领域中具有应用。作为该项目的教育组成部分，Chalifoux教授开发了一个外展计划，重点是指导来自低收入，第一代大学家庭的初中和高中学生以及在科学方面代表性不足的群体。该项目与位于内华达州里诺地区的初中和高中建立了联系。 访问高中学生密切合作，研究生和本科化学专业的学生在科学相关的活动与研究项目在Chalifoux集团。本项目主要研究了炔和炔酮的环化和环加成反应。这项研究开发了一种操作简单的合成方法，将容易获得的炔，二炔和二烯原料转化为复杂的环状和多环目标分子。简单的共轭炔和更复杂的共轭和交叉共轭多炔探索作为底物的狄尔斯-阿尔德环加成反应。这些在多组分/串联环化反应中得到进一步阐述，这些反应被设计为在单个反应步骤中产生多个新的碳-碳键和环，具有区域和立体化学控制。该研究通过快速生成生物相关化合物库，在药物合成领域和医学领域具有广泛的应用。除了在初中和高中的活动，职业奖支持夏季研究活动在内华达州的大学。 这改善了招聘人数不足的学生进入科学，技术，工程和数学（STEM）的职业生涯，并增加了学生在科学方面的保留。