W. Li
2015
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Journal
Chinese Journal of Synthetic Chemistry
Abstract
4-( 3-Chloropropoxy)-3-methoxybenzonitrile( 3) was prepared by alkylation of 4-hydroxy-3-methoxy benzaldehyde with 1-bromo-3-chloropropane,then reaction with hydroxylamine. N-[5-( 3-chloropropoxy) ]-2-nitrile-4-methoxyphenyl-N,N-dimethylformamide( 6) was prepared by nitration and reduction of 3,then reaction with N,N-dimethylformamide dimethyl acetal. A novel series of 4-aminoquinazoline derivatives( 9a ~ 9g) were synthesized by cyclization of 6 with 3-chloro-4-fluoroaniline,and then substitution reaction with aromatic ethers. The structures of intermediates and 9a ~ 9g were characterized by1 H NMR,13 C NMR,IR and elemental analysis. Preliminary bioassay tests showed that 9a ~ 9g had certain activities against Bcap-37 cell proliferation. Among them the inhibition of 3-chloro-4-fluoro-phenyl-{ 7-[3-( 2-chlorophenoxy)-propoxy]-6-methoxy-quinazolin-4-yl} amine( 9d)and 5-chloro-2-{ 3-[4-( 3-chloro-4-fluorophenylamino)-6-methoxy-quinazolin-7-yloxy]-propoxy}-benzaldehyde( 9g) against Bcap-37 cell were 61. 4%,78. 9% at 10 μmol·L- 1,respectively.