Journal of Guangdong University of Technology ›› 2020, Vol. 37 ›› Issue (03): 95-100.doi: 10.12052/gdutxb.190070

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A New Synthetic Route for Small-Molecule Inhibitor of Prostate Specific Membrane Antigen

Xiao Qing-wei, Chang Yuan-yuan, Liu Qi-fa, Zang Xiao-hao, Hu Meng-meng, Zhou Wei   

  1. School of Biomedical and Pharmaceutical Sciences, Guangdong University of Technology, Guangzhou 510006, China
  • Received:2019-05-15 Online:2020-05-12 Published:2020-05-21

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Abstract: Small molecular inhibitor with Glu-Urea skeleton of Prostate Specific Membrane Antigen was synthesized by 7 steps using L-glutamic acid and L-lysine as starting materials. The yield of each step was higher than 60% except for the synthesis of L-di-tert-butyl glutamate. The total yield of the route was 18%. The products were characterized by 1H NMR, 13C NMR and HR-MS(ESI). A new synthetic method was designed for the synthesis of intermediate tert-butyl N6-(((9H-fluoren-9-yl)methoxy)carbonyl)-L-lysinate, which realized the deprotection of lysine alpha amino group and the protection of carboxyl group by Boc in one step, simplified the reaction steps and increased the synthetic yield of compound 3 from 20% to 70%.

Key words: L-glutamic acid, L-lysine, prostate specific membrane antigen, small-molecule inhibitors

CLC Number: 

  • O621.3
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