Cinchona alkaloid derivative-catalyzed enantioselective synthesis via a Mannich-type reaction and antifungal activity of β-amino esters bearing benzoheterocycle moieties.
An efficient synthesis of highly functionalized chiral β-amino ester derivatives containing benzothiophene and benzothiazole moieties is developed by a Mannich-type reaction using a cinchona alkaloid-derived thiourea catalyst. The desired products were obtained in good yields and high enantioselectivities (~86% yield, >99% ee) using to the optimized reaction conditions. The synthesized compounds were characterized by 1H-NMR, 13C-NMR, IR, and HREI-MS analyses. The bioassays identified that compound 5dr has excellent antifungal activity, with a 60.53% inhibition rate against F. oxysporum, higher than that of the commercial agricultural fungicide hymexazol, whose inhibition rate was 56.12%.
Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China. hanx@gzmu.edu.cn.
Han
H
Xiao
Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China. fangwu90@163.com.
Fang
F
Wu
Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China. s2012l@sina.com.
Li
L
Shi
Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China. yan.zhilie@163.com.
Zhiwei
Z
Chen
Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China. sushihu999@gmail.com.
Shihu
S
Su
Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China. chtang1122@163.com.
Chenghao
C
Tang
Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China. wanghongtao1115@126.com.
Hongtao
H
Wang
Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China. aning072@126.com.
Zhining
Z
Li
Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China. lmcuvhn1987@163.com.
Meichuan
M
Li
Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China. shiqingcai1988@163.com.
Qingcai
Q
Shi
D000596:Amino Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D052160:Benzothiazoles / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D004952:Esters; D005670:Fusarium / Q000187:drug effects / Q000254:growth & development; D008826:Microbial Sensitivity Tests; D010080:Oxazoles / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000737:chemistry*; D013890:Thiourea / Q000737:chemistry*
D000596:Amino Acids; D000935:Antifungal Agents; D052160:Benzothiazoles; D002930:Cinchona Alkaloids; D004952:Esters; D010080:Oxazoles; D013876:Thiophenes; C531211:hymexazol; D013890:Thiourea