Reinvestigations into synthesis of allyldithiocarbamates and their intramolecular cyclization: synthesis and antihyperglycemic activity of 2-thioxothiazolidine-4-alkanoates

Reinvestigating the synthesis of allylthiocarbamates from MBH derivatives revealed that they are obtained more efficiently from allylbromides in isopropanol rather than acetates in water. Further unlike reported, the base-mediated intramolecular cyclization of these allyldithiocarbamates give substi...

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Published in:Tetrahedron 2014-09, Vol.70 (38), p.6841-6850
Main Authors: Dighe, Shashikant U., Yadav, Veena D., Srivastava, Rohit, Mishra, Akanksha, Gautam, Sudeep, Srivastava, Arvind K., Balaramnavar, Vishal M., Saxena, Anil K., Batra, Sanjay
Format: Article
Language:English
Subjects:
Allyldithiocarbamate
Morita–Baylis–Hillman
Nitrocinnamates
Quaternary carbon
α-Addition
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Summary:Reinvestigating the synthesis of allylthiocarbamates from MBH derivatives revealed that they are obtained more efficiently from allylbromides in isopropanol rather than acetates in water. Further unlike reported, the base-mediated intramolecular cyclization of these allyldithiocarbamates give substituted 2-thioxothiazolidine-4-alkanoates instead of substituted 1,3-thiazines and the reaction was restricted to 2- or 4-nitrophenyl carrying substrates. Screening of these products for antihyperglycemic activity revealed that 5bC displays significant activity via partial agonist activity on PPARγ at transcriptional level, which was corroborated by molecular docking studies. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.07.044