Kin Chiu Fong

SYNTHESIS, REACTION, AND CYTOTOXICITY OF NOVEL PROPARGYLIC SULFONES

Abstract Propargylic sulfones 1 and 2 have been synthesized for their potent interactions with DNA. The crown ether conjugate 8 was also prepared from 1 under carefully established reaction conditions. The synthesized propargylic sulfones 2, 5, and 8 exhibited high reactivity toward sulfur-, nitrogen-, and oxygen-containing nucleophiles. Compound 1 showed an IC50 of 5.3×10−6 M against KB/P cancer cells comparable with that of the clinically used agent 5-FU.

Remarkable tethering effect on DNA cleavage of propargylic sulfone conjugates with intercalating moieties

A number of novel propargylic sulfone conjugates 3 and 4 with intercalating moieties were synthesized and evaluated for DNA cleavage activity through nucleic base alkylation. A remarkable enhancement in DNA cleaving potency was observed with those conjugates 3 possessing a suitable spacer, a right attachment point at the aromatic ring, and a good intercalator.

First synthesis of cis-enediynes from 1,5-diynes by an acid-mediated allylic rearrangement

Abstract The first synthesis of cis -enediynes 11 from 1,5-diyne 7 is achieved by treatment with 1 equivalent of CSA in CH 2 Cl 2 at 20 °C in the presence of ROH or RSH to provide 11 as the major products in good yield. An 11-membered ring enediyne 15 was prepared similarly in 47% yield.

DNA cleavage of novel propargylic sulfones. Enhancement of potency via intercalating interaction

Abstract A number of novel hydroxy propargylic sulfones 7–15 were synthesized as DNA cleaving agents. Enhancement of DNA cleavage potency was observed with those compounds which could interact with DNA through intercalation of the extended aromatic rings.