CAREER: Harnessing the reactivity of neutral aminyl radicals for complex heterocycle synthesis

通过这个职业奖，化学系的化学合成计划支持韦恩州立大学的詹妮弗·L·斯托克迪尔教授的研究计划。斯托克迪尔教授正在研究形成不寻常化学结构的反应。该项目提供了一种新的方法来制备具有碳和氮原子(杂环)的环结构，包括具有多种生物学作用的分子，如血管松弛、细胞毒和神经活性。在她的项目的教育部分，斯托克迪尔教授正在开发一个以促进女性和少数族裔在科学领域的发展为中心的外展项目。通过她的研究计划，研究生和本科生接受研究方面的实践培训。外展活动向中学女生传授基本的有机化学概念，向她们灌输对科学发现的热情，无论她们最终是否追求科学事业。此外，斯托克迪尔教授与AlChemie合作开发新的活动，帮助学习具有挑战性的有机化学概念，并为现有的本科生和研究生课程创建新的主动学习模块。斯托克迪尔教授正在研究使用中性氨基的新型环化反应。这些反应性实体具有快速组装复杂分子的潜力，这可能对随后的一系列应用有用。中性氨基由于其不可预测的反应性，以前在合成序列中没有被广泛应用。斯托克迪尔博士正在测试一项关于互补自由基受体的必要性质的假设，以及开发避免使用有毒试剂的氨基生成方法。这个项目提供了各种已知的和新的具有不同生物活性的杂环分子的途径。这项研究还为中性氨基自由基的反应性提供了新的理解，使多环杂环的快速组装成为可能。化学家可预见的新反应方法的发展有助于扩大可用于筛选文库的化学空间的范围。最终，对新分子的接触可能使人们能够识别探索基本生物学功能的分子结构，并可能成为制药应用中的主要目标。本科生和研究生在斯托克迪尔实验室接受有机化学和科学方法方面的培训。斯托克迪尔博士还通过发展女性科学研究生(GWIS)小组建立了一个女性科学家网络，以便女性能够找到在研究生院和整个科学职业生涯中取得成功所需的支持。

Through this CAREER Award the Chemical Synthesis Program in the Chemistry Division is supporting the research program of Professor Jennifer L. Stockdill of Wayne State University. Professor Stockdill is investigating reactions to form unusual chemical structures. This project provides a new method to prepare ring structures with carbon and nitrogen atoms (heterocycles), including molecules with a diverse set of biological actions such as vasorelaxant, cytotoxic, and neurologic activity. In the educational component of her project, Professor Stockdill is developing an outreach program centered on advancing women and minorities in science. Through her research program, graduate and undergraduate students receive hands-on training in research. The outreach activities teach basic organic chemistry concepts to middle school girls, instilling in them an enthusiasm for scientific discovery, whether they ultimately pursue a career in science or not. Additionally, Professor Stockdill collaborates with Alchemie to develop new activities that aid in learning challenging organic chemistry concepts, and she creates new active learning modules for existing undergraduate and graduate courses. Professor Stockdill is investigating novel cyclization reactions employing neutral aminyl radicals. These reactive entities have potential for the rapid assembly of complex molecules that may be useful for a range of subsequent applications. Neutral aminyl radicals have not previously been widely applied in synthetic sequences because of their unpredictable reactivity. Dr. Stockdill is testing a hypothesis regarding the necessary properties of the complimentary radical acceptors, as well as developing methods for aminyl radical generation that avoid the use of toxic reagents. This project provides access to a variety of both known and novel heterocyclic molecules with a diverse set of bioactivities. This research also provides new understanding of the reactivity of neutral aminyl radicals, enabling the rapid assembly of polycyclic heterocycles. The development of new reaction methods that can be employed predictably by chemists contributes broadly to improving the scope of chemical space available for screening libraries. Ultimately, access to new molecules may enable the identification of molecular structures that probe fundamental biological functions and potentially serve as lead targets in pharmaceutical applications. Undergraduate and graduate student are trained in organic chemistry and the scientific method in the Stockdill laboratory. Dr. Stockdill also creates a network of female scientists through the development of a Graduate Women in Science (GWIS) group, so that women can find the support they need to be successful in graduate school and throughout their careers in science.