CINCHONA ALKALOID THIOUREA-CATALYZED ONE-POT SYNTHESIS AND BIOSELECTIVE ACTIVITIES OF β-AMINO ACID ESTER DERIVATIVES CONTAINING A PYRIMIDINE MOIETY

We have studied the synthesis of enantiomerically pure optically active beta-amino acid ester derivatives with good biological activities. Here, we report that both enantiomers of beta-amino acid ester derivatives that contain a pyrimidine moiety can be produced in an enantioselective Mannich-type one-pot reaction with good yields and excellent enantiomeric excess (up to >99% ee) by chiral cinchona alkaloid thiourea catalysts. An evaluation of the antiviral activities of our reaction products against tobacco mosaic virus (TMV) was promising with high and selective biological activities. Compound (-)-4h showed an excellent anti-TMV activity (curative activity, 56.1%; inactivation activity, 70.7%; protection activity, 95.7%) at 500 mu g/mL. These values exceed those of the commercially available antiviral agent, ningnanmycin (curative activity, 52.6%; inactivation activity, 62.0%; protection activity, 90.2%). These novel chiral compounds could be used as protective agents against TMV disease.