Unexpected formation of N-METHYLFULLEROPYRROLIDINE (cas 151872-44-5)s by the reaction of fullerene and gossypol and their bioactivity

Add time:07/11/2019    Source:sciencedirect.com

Reaction of fullerene, sarcosine and gossypol through the Prato reaction resulted in some unexpected N-methylfulleropyrrolidines. These fulleropyrrolidines were fully characterized via rigorous structure determination through multiple spectral experiments, which included 1D, 2D NMR, FT-IR, MS and X-ray crystallography. During the reaction, gossypol decomposed into benzaldehyde which was successfully detected as a new intermediate through GC–MS. In an in vitro assay of NO radical induced apoptosis in 3T3L1 cells, N-methylfulleropyrrolidine (2) and N-methyl-2,2-dimethylfulleropyrrolidine (3) showed dose dependent and stronger radical scavenging activities than the parent fullerene.

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