Synthesis of 1-(2-aminoethylsulfonyl)-2-phosphorylpyrrolidines via consecutive Arbuzov and aza-Michael reactions and their antitumor activity

摘要

1-(2-Aminoethylsulfonyl)-2-phosphorylpyrrolidines have been synthesized via boron trifluoride-catalyzed Arbuzov reaction of 2-ethoxy-1-(vinylsulfonyl)pyrrolidine with triethyl phosphite followed by aza-Michael reaction of thus obtained 2-phosphoryl-1-(vinylsulfonyl)pyrrolidine with secondary amines. The cytotoxicity of the prepared 1-(2-aminoethylsulfonyl)-2-phosphorylpyrrolidines against M-Hela tumor cell line is comparable with that of tamoxifen, whereas the cytotoxicity against normal cell line is twofold lower.