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Paper | Regular issue | Vol 96, No. 8, 2018, pp.1383-1397
Published online, 20th July, 2018
DOI: 10.3987/COM-18-13918
Cinchona Alkaloid Thiourea-Catalyzed One-Pot Synthesis and Bioselective Activities of β-Amino Acid Ester Derivatives Containing a Pyrimidine Moiety

Song Bai,* Shan Liu, Yunying Zhu, Xian Wei, Kunhong Zhao, Weihua Li, and Qin Wu*

*School of Chemical Engineering, Guizhou Institute of Technology, 1st, Caiguan Road, Yunyan District, Guiyang City, Guizhou Province 550003, China

Abstract

We have studied the synthesis of enantiomerically pure optically active β-amino acid ester derivatives with good biological activities. Here, we report that both enantiomers of β-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 μg/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.