Synthesis, Charaction And Biological Activities Of Arylaminoacetic Acid Derivatives

Abstract There are two parts in this paper. One is the synthesis of ten novel 1-arylaminoacetyl-4-arylacetyl thiosemicarbazides using phase transfer catalyst under ultrasonic irradiation. This method has advantages of good yields, short reaction time, easy preparation and mild reaction conditions. In order to synthesize the target molecules, tweleve important intermediate products were also prepared. The structures of all the compounds were characterized by melting point, elemental analysis,IR,1H NMR and 13C NMR spectra. Preliminary biological activity study indicated that all compounds show promoting effects on the growth of corn root in lower concentration. Partial compounds have promoting effects on the growth of corn seedling. However, in higher concentration, the compounds show inhibitory effects on the growth of both corn seedling and corn root. The other one is the synthesis of ten new acetylated β-lactosyl N-(N-acetyl-N-phenylglycyl)-N-phenyl-glycine ester and acetylatedβ-mactose N-(N-acetyl-N-phenylglycyl)-N-phenyl-glycine ester using phase transfer catalyst under stereospecificity. In order to synthesize the target molecules, tweleve correlative intermediate products were also prepared. The structures of all the compounds were characterized by melting point, elemental analysis,MS,IR,1H NMR and 13C NMR spectra. β-conformers were identified for the new compounds. NMR (TOCSY, gCOSY, HMBC, HSQC, HOM2DJ) was investigated in detail by 2D NMR technique. The C, H chemical shifts were assigned for the studied compound, and the coupling constant, J values, were also given out. The assignment for C, H chemical shifts of seven acetyls has not been reported until now, so this research is meaningful for the structure study of this kind of compounds. Preliminary antitumor activity in vitro of the new compounds indicated that the compounds have obvious inhibitory effect on human leukaemia cell (HL-60) and human galactophore cancer cell (MDA-MB-468) in the concentration of 10-4 mol/L. This result is a basis for further study on the synthesis and biological activity of this kind of compounds.