一些新型糖基单环β-内酰胺的合成及其抗菌活性
Synthesis and antimicrobial activity of some new sugar-based monocyclic beta-lactams.
作者信息
Jarrahpour A A, Shekarriz M, Taslimi A
机构信息
Chemistry Department, College of Sciences, Shiraz University, Shiraz 71454, Iran.
出版信息
Molecules. 2004 Jan 31;9(1):29-38. doi: 10.3390/90100029.
Abstract
The syntheses of some new sugar-based monocyclic beta-lactams possessing several other functionalities in addition to the carbohydrate moiety are described. The key step was the Staudinger [2+2] cycloaddition of chiral carbohydrate Schiff base 5 with phthalimidoacetyl chloride to yield the sugar-based monocyclic beta-lactam 6 as a single isomer. Treatment of protected beta-lactams 6 and 8 with methylhydrazine afforded the free amino beta-lactams 9 and 10. Acylation of these free amino beta-lactams with benzoyl, phenoxyacetyl, cinnamoyl and phenylacetyl chloride in the presence of pyridine afforded beta-lactams 11a-d and 12a-d. Some of these novel beta-lactams were found to be active against Staphilococcus citrus, Klebsiella pneumoniae, Escherichia coli and Bacillus subtilis.
摘要
本文描述了一些新型糖基单环β-内酰胺的合成，这些化合物除碳水化合物部分外还具有其他几种官能团。关键步骤是手性碳水化合物席夫碱5与邻苯二甲酰亚胺乙酰氯进行施陶丁格[2+2]环加成反应，生成单一异构体的糖基单环β-内酰胺6。用甲基肼处理受保护的β-内酰胺6和8，得到游离氨基β-内酰胺9和10。在吡啶存在下，这些游离氨基β-内酰胺与苯甲酰氯、苯氧乙酰氯、肉桂酰氯和苯乙酰氯进行酰化反应，得到β-内酰胺11a-d和12a-d。发现其中一些新型β-内酰胺对柑橘葡萄球菌、肺炎克雷伯菌、大肠杆菌和枯草芽孢杆菌具有活性。
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