SYNTHETIC APPROACHES TO ALKALOIDS VIA NITRILE YLIDS

通过腈基合成生物碱的方法

• 批准号: 3280503
• 负责人: THOMAS Stuart LIVINGHOUSE
• 金额: $ 6.15万
• 依托单位: UNIVERSITY OF MINNESOTA
• 依托单位国家: 美国
• 财政年份: 1983
• 资助国家: 美国
• 起止时间: 1983-04-01 至 1986-09-09
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/3280503
• 关键词: Ehrlich's tumor; alkaloids; alkenes; ascites; azo compounds; cyanides; drug design /synthesis /production; neurotoxins; physostigmine; ylide

Novel methods envisaged for the elaboration of biologically active alkloids are described which rely upon intramolecular 1, 3-dipolar cycloaddition reactions of nitrile and azomethine ylids with appropriately situated olefins. Immediate synthetic targets include (a) the Amarylidaceae alkaloid pretazettine which has shown marked activity against Ehrlich ascites carcinoma in mice, (b) the convulsive alkaloid dendrobine present in the Chinese tonic Chin Shih Hu, (c) the paralytic agent erythramine, and (d) the Pyrrolizidine alkaloid heliotridine. Moreover, extention of this methodology to the appropriate substrate should facilitate an expedient synthesis of the neurotoxis Physostigmine alkaloid eserethole.

用于制备生物活性生物碱的新方法 其依赖于分子内1，3-偶极环加成 腈和甲亚胺叶立德与适当位置的 烯烃。 直接的合成目标包括（a）石蒜科 一种对埃利希氏病显示出显著活性的生物碱普雷扎汀 小鼠腹水癌，（B）存在惊厥生物碱石斛碱 （c）麻痹剂丁胺，以及 (d)吡咯里西啶生物碱天芥菜碱。 此外，这一延伸 适当的基板的方法应有助于一种权宜之计 神经毒素毒扁豆碱生物碱艾司瑞素的合成。