Synthesis of novel gem-difluorinatedcyclopropane hybrids: Applications for DNA cleavage agents switched by photo irradiation

The preparation and properties of 1,1-difluorocyclopropane derivatives

“…Recently, there has been much interest in the synthesis of organic compounds that can cleave DNA following photoirradiation. Ninomiya et al described anthracene–difluorocyclopropane hybrids, which were modified in order to maximize DNA cleavage [ 126 ]. DNA damage was induced due to the radical decomposition of the cyclopropane ring.…”

Recent advances in the syntheses, transformations and applications of 1,1-dihalocyclopropanes

“…47 Ninomiya et al reported that the gem-difluorocyclopropane derivative of 9-anthracenecarboxylic acid displayed a DNA cleavage property upon photoirradiation. 123 A large number of nucleoside analogues have been synthesized as potential chemotherapeutic agents, especially as antiviral agents and incorporation of fluorine substituents in these compounds has shown benefits such as advanced action, greater bio-availability and retarded drug metabolism for several compounds studied. 47 Recently Kailani et al synthesized and studied the antimicrobial activities of dicarbamates prepared from various arylisocyanates and (1R,3S)-2,2-dichloro-3-hydroxymethylcyclopropylmethanol.…”

Synthesis of Novel gem-Difluorinatedcyclopropane Hybrids: Applications for Material and Medicinal Sciences

“…Form these results, we anticipated that our anthracene-gemdifluorocyclopropane compounds might display DNA cleavage activity by photo irradiation, because it was reported that decomposition of a gemdifluorocyclopropane ring proceeded via a radical intermediate (24), and it has been suggested that DNA damage was caused by radical species (25) (Figure 4). Hence, we prepared optically active gem-difluorocyclopropane derivatives 25-27 from (S,S)-l\ or (R,R)-2\ ( Figure 5) and tested their DNA cleavage activities (26) (Figure 6). We expected that enhanced DNA cleavage activity might be obtained by introduction of the terminal amino group in our compounds due to increased interaction of the anionic part of DNA.…”