SYNTHESIS AND BIOASSAY OF HIGHLY FUNCTIONALIZED PYRROLES

高功能化吡咯的合成与生物测定

• 批准号: 2183641
• 负责人: JOHN T. GUPTON
• 金额: $ 11.1万
• 依托单位: UNIVERSITY OF CENTRAL FLORIDA
• 依托单位国家: 美国
• 财政年份: 1992
• 资助国家: 美国
• 起止时间: 1992-05-01 至 1995-08-30
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/2183641
• 关键词: analog; antibiotics; antineoplastics; bioassay; chemical synthesis; drug screening /evaluation; pyrroles; vinblastine

One of the more specific goals of our research group has been to uncover useful synthetic methodology related to the chemistry of vinamidinium salts and their derivatives. One important class of compounds for which vinamidinium salts might serve as precursors are pyrroles and related compounds. The synthesis of pyrrole derivatives has been actively pursued in recent years due in part to the pharmacological properties of certain members of this class of substances. The goal of the organic synthesis described herein will be to establish and understand the use of vinamidinium salts and related compounds as efficient and useful reagents for the preparation of functionalized pyrroles. We propose a three phase study of the reaction of alpha-amino acid esters and related compounds with vinamidinium salts. Phase one will involve looking at substituent effects of the reactants in the condensation process. Phase two will deal with analogous reactions with unsymmetrical salts (vinamidinium and chloropropeniminium). Phase three will involve the generation of disubstituted chloropropeniminium salts and their conversion to regioselectively functionalized trisubstituted pyrroles. The overall study should define and delineate this methodology for the preparation of functionalized pyrroles.

我们研究小组的一个更具体的目标是揭示 与vinamidinium的化学有关的有用的合成方法 盐及其衍生物。 一类重要的化合物， 可用作前体的vinamidinium盐是吡咯和相关的 化合物. 吡咯衍生物的合成一直很活跃 近年来，由于其药理学特性， 这类物质的某些成员。 有机的目标 本文所述的合成将是建立和理解 作为有效和有用试剂的vinamidinium盐和相关化合物 用于制备官能化的吡咯。 我们提出了三个阶段 α-氨基酸酯与相关化合物反应的研究 与vinamidinium盐。 第一阶段将涉及寻找取代基 反应物在缩合过程中的作用。 第二阶段将 处理与不对称盐（vinamidinium和 chloropropeniminium）。 第三阶段将涉及生成 二取代的氯丙烯亚胺鎓盐和它们转化成 区域选择性官能化的三取代吡咯。 整体 研究应界定和描述这种方法， 功能化吡咯。