Jarrahpour Aliasghar, Rostami Maryam, Sinou Véronique, Latour Christine, Djouhri-Bouktab Lamia, Michel Brunel Jean
Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454, Iran.
Aix-Marseille Université, UMR-MD3 Relation hôte-parasites, Physiopathologie & Pharmacologie, Faculté de pharmacie, Bd Jean Moulin, F-13385, Marseille, France.
Iran J Pharm Res. 2019 Spring;18(2):596-606. doi: 10.22037/ijpr.2017.2024.
Fifteen novel β-lactams bearing N-ethyl tert-butyl carbamate group 5a-o and fifteen N-(2- aminoethyl) β-lactams were synthesized by [2+2] ketene-imine cycloaddition reaction (Staudinger). The cycloaddition reaction was found to be totally diastereoselective leading exclusively to theformation of -β-lactam derivatives. These newly synthesized β-lactams were evaluated for their antimalarial activity against K14 resistant strain and showed good to excellent EC50 values. Of the thirty β-lactams tested, and showed IC50 < 20 µM while , , , , , , , , and exhibited IC50 <50 . Compounds 5c, 5h, and 5q-t were examined for their anticancer properties against K562 cell line and 5s showed the best activity. Compounds , , , were tested against , and showed no activity below 125 µg/mL.
通过[2+2]乙烯酮-亚胺环加成反应（施陶丁格反应）合成了15种带有N-乙基叔丁基氨基甲酸酯基团的新型β-内酰胺5a-o和15种N-(2-氨基乙基)β-内酰胺。发现该环加成反应具有完全的非对映选择性，仅生成β-内酰胺衍生物。对这些新合成的β-内酰胺针对K14耐药菌株的抗疟活性进行了评估，结果显示出良好至优异的半数有效浓度（EC50）值。在所测试的30种β-内酰胺中，[此处可能遗漏了具体化合物编号]显示半数抑制浓度（IC50）<20 μM，而[此处可能遗漏了具体化合物编号]表现出IC50<50[此处单位缺失]。对化合物5c、5h和5q - t针对K562细胞系的抗癌特性进行了研究，5s显示出最佳活性。对[此处可能遗漏了具体化合物编号]针对[此处可能遗漏了具体测试对象]进行了测试，在125 μg/mL以下未显示活性。
