Synthesis of new analogs of N-substituted(benzoylamino)-1,2,3,6-tetrahydropyridines

IF 2.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Open Chemistry Pub Date : 2024-04-09 DOI:10.1515/chem-2023-0183

Shasline Gedeon, Laila M. Boyd, Marlee Avril, Madhavi Gangapuram, Kinfe K. Redda, Tiffany W. Ardley

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引用次数: 0

Abstract

The tetrahydropyridine (THP) moiety is notably present in synthetic and natural products, playing a cardinal role in the food, cosmetic, and pharmaceutical industries. The THP structure is an instrumental constituent and is widely found in alkaloids that have therapeutic properties against inflammation, cancer, the nervous system, and bacterial infections. The use of THPs has gained traction, so it is imperative to increase the structural database through the synthesis of THP derivatives. The focus of this study is to make structural modifications to the benzene ring portion of the lead compound while keeping the pyridine ring constant. Eleven novel THP analogs were synthesized using a four-step synthetic approach involving partial reduction of N-substituted ylides into 1,2,3,6-THPs. The results illustrate that 11 THPs were successfully synthesized in low to moderate yields. Flash chromatography was utilized for purification. Proton nuclear magnetic resonance, deuterium oxide exchange, carbon nuclear magnetic resonance, infrared spectroscopy, and CHN elemental analysis were utilized to characterize the THP analogs. This study aids in contributing knowledge to the THP database.

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合成 N-取代(苯甲酰氨基)-1,2,3,6-四氢吡啶的新类似物

四氢吡啶（THP）分子显著存在于合成产品和天然产品中，在食品、化妆品和制药行业中发挥着重要作用。THP 结构是一种重要成分，广泛存在于对炎症、癌症、神经系统和细菌感染有治疗作用的生物碱中。THP 的应用已越来越广泛，因此通过合成 THP 衍生物来增加结构数据库势在必行。本研究的重点是对先导化合物的苯环部分进行结构改造，同时保持吡啶环不变。采用四步合成法，将 N-取代的酰化物部分还原成 1,2,3,6-THP，合成了 11 种新型 THP 类似物。结果表明，成功合成了 11 种 THP，收率从低到中等。采用闪速色谱法进行纯化。质子核磁共振、氧化氘交换、碳核磁共振、红外光谱和 CHN 元素分析被用来表征 THP 类似物。这项研究有助于为 THP 数据库贡献知识。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Open Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

3.80

自引率

4.30%

发文量

审稿时长

6 weeks

期刊介绍： Open Chemistry is a peer-reviewed, open access journal that publishes original research, reviews and short communications in the fields of chemistry in an ongoing way. The central goal is to provide a hub for researchers working across all subjects to present their discoveries, and to be a forum for the discussion of the important issues in the field. The journal is the premier source for cutting edge research in fundamental chemistry and it provides high quality peer review services for its authors across the world. Moreover, it allows for libraries everywhere to avoid subscribing to multiple local publications, and to receive instead all the necessary chemistry research from a single source available to the entire scientific community.