| 4-[1-烷基-5-氧代-1H-1,2,4-三唑-4(5H)-基]-苯甲酸的合成 |
| 投稿时间：2013-01-25 修订日期：2013-04-08 点此下载全文 |
| 引用本文：陈海,姚建忠,盛春泉,缪震元,张万年.4-[1-烷基-5-氧代-1H-1,2,4-三唑-4(5H)-基]-苯甲酸的合成[J].药学实践杂志,2013,31(6):442~445 |
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| 基金项目:国家自然科学基金(30772674、30930107). |
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| 中文摘要:目的 制备用于全合成卡泊芬净类环六脂肽抗真菌剂的关键脂肪酸侧链4-[1-烷基-5-氧代-1H-1,2,4-三唑-4(5H)-基]-苯甲酸(5)。方法 以对氨基苯甲酸(1)为起始原料,经氨基苯氧羰酰化、肼解、甲脒环合及N-烃化4步反应制备目标化合物。结果 以42.9%~46.2% 的总收率成功合成了目标化合物5a~5n,其结构经电喷雾质谱(ESI-MS)和氢谱(1H NMR)确证;所有目标化合物均为首次报道。结论 该合成路线具有操作简便及收率高等优点,适合工业化生产。 |
| 中文关键词:4-[1-烷基-5-氧代-1H-1,2,4-三唑-4(5H)-基]-苯甲酸 合成 环六脂肽 卡泊芬净 抗真菌 |
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| Synthesis of 4-[1-alkyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl] benzoic acids |
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| Abstract:Objective To prepare 4-[1-alkyl-5-oxo-1H-1,2,4-triazol-4 (5H)-yl] benzoic acids (5), which was the key fatty acid chain pharmaceutical intermediates for the total synthesis of novel caspofungin-like cyclohexa lipopeptide antifungal agents.Methods Starting from 4-aminobenzoic acid (1), the target compounds 5a~5n were prepared via amino phenoxy-carbonyl acylation, hydrazinolysis, formamidine cyclization, and the N-alkylation reaction, respectively. Results Target compounds 5a~5n had been successfully synthesized with the overall yield ranged from 42.9% to 46.2%. Their structures were confirmed by ESI-MS and 1H-NMR spectra. All target compounds were reported for the first time.Conclusion The process developed had several advantages such as convenient workup and high yield, which was suitable to industrial production. |
| keywords:4-[1-alkyl-5-oxo-1H-1,2,4-triazol-4 (5H)-yl] benzoic acid synthesis cyclohexalipopeptide caspofungin antifungal |
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