2-[4-取代苯基-2-氧-3-酰氨基-1-吖丁啶基]-2-苯基乙酸类化合物的合成

The Synthesis of 2-(4-Substituted Phenyl-2-oxo-3-amido-1-azetidinyl)-2-phenylacetic Acids

近年来β-内酰胺酶抑制剂的研究引起人们的关注[1,2],考虑到单环β-内酰胺类的作用模式与双环β-内酰胺的作用可能相似,我们曾合成了两类β-内酰胺单环化合物[3,4].

A method is described for the synthesis of the title compounds starting from sodiumazide and D-phenylglycine.Oyclocondensation between azidoacetyl chloride and iminocompounds in the presence of triethylamine at-78℃leads to stereospecific synthesisof cis-methyl-2-(4-substituted phenyl-2-oxo-3-azido-1-azetidinyl)-2-phenylacetates.The azido group can be reduced by catalytic hydrogenation or with hydrogen sulfide toafford amineβ-lactam which are acylated to form a-amido-β-lactams.Ester group canbe selectively hydrolyzed under mild basic condition without effecting either theβ-lactam ring or the amide side chain.Twenty title compounds have been synthesizedand nine of them show inhibitory activity againstβ-lactamase.