Spirobarbiturates with a pyrrolizidine moiety: synthesis, structure and biological evaluation
Arthur A Puzyrkov1, Andrew S Drachuk2, Ekaterina A Popova3
1Saint Petersburg State University, Universitetskaya nab. 7/9, 199034, St. Petersburg, Russian Federation.
None:
Polycyclic spirobarbiturates containing a pyrrolizidine moiety were synthesized via a one-pot three-component 1,3-dipolar cycloaddition reaction of alloxan, ʟ-proline and N-substituted maleimides. The reaction stereoselectivity was found to depend on the nature of substituents in the maleimide: in most cases the endo-isomer is the main (or only) product, but for some N-arylmaleimides the exo-product is predominant. The proposed mechanism is discussed, and the products were characterized by detailed spectral analysis. The configuration of the stereocenters was determined by X-ray diffraction analysis (XRD) for two adducts, followed by Hirshfeld surface analysis. The antiproliferative effect of the synthesized compounds against cancer cell lines was assessed.
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