Discovery of Novel Sultone Fused Berberine Derivatives as Promising Tdp1 Inhibitors.

ABSTRACT: A new type of berberine derivatives was obtained by the reaction of berberrubine with aliphatic sulfonyl chlorides. The new polycyclic compounds have a sultone ring condensed to C and D rings of a protoberberine core. The reaction conditions were developed to facilitate the formation of sultones with high yields without by-product formation. Thus, it was shown that the order of addition of reagents affects the composition of the reaction products: when sulfochlorides are added to berberrubine, their corresponding 9-O-sulfonates are predominantly formed; when berberrubine is added to pre-generated sulfenes, sultones are the only products. The reaction was shown to proceed stereo-selectively and the cycle configuration was confirmed by 2D NMR spectroscopy. The inhibitory

SUBMITTER: Gladkova ED 

PROVIDER: S-EPMC8037669 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature