Design and Synthesis of α,β-Epoxyketones as New Anticancer Agents

Abstract

As epoxy functional group has high anticancer activity, α,β-epoxyketones were designed and synthesized as new anticancer agents, and their structures were confirmed by UV, 1 H NMR, IR, MS technigeces and elemental analysis. Their in vitro anticancer activities were evaluated by MTT method and the results showed that the compound 4c exhibited good activity with IC 50 of 17.8, 22.0 and 24.1 µg/mL against A-549, Hela and HepG2 cells, respectively. The dose of LD50 of the mice by intragastric administration was 1864.4 mg/kg. Therefore, the α,β-epoxyketones could potentially provide as new anticancer agents.

DNA-Compatible Synthesis of α,β-Epoxyketones for DNA-Encoded Chemical Libraries

“…α,β-Epoxyketone is featured as an epoxide ring along with adjacent ketone, including disubstituted and trisubstituted types. This kind of drug-like moiety is present in several molecules with biological activities that are presumably associated with the epoxide moiety (Figure A). − Therefore, it is of significance to incorporate α,β-epoxyketones into DNA-encoded chemical libraries to generate structurally focused libraries. From a synthetic perspective, α,β-epoxyketone could be achieved from the epoxidation of alkene or via Darzens condensation between α-chlorinated ketone and aldehyde.…”

Design, Synthesis, and Antifungal Activity of Novel Thiochromanone Derivatives Containing 1,3,4-Oxadiazole Skeleton

“…近年文献报道显示: 2,3 位修饰的硫色 满酮类化合物具有较好的抗真菌活性(图 1). 如在硫色 满酮 2-位上引入噻二唑环的噻二唑类硫色满酮(图 1, A) [5] ; 3-位引入硫代亚甲基结构的硫代亚甲基硫色满酮 (图 1, B) [6] ; 硫色满酮 3-位通过羟醛缩合反应引入吲哚 亚甲基结构的吲哚亚甲基硫色满酮(图 1, C) [7] ; 硫色满 酮 2 位引入哌嗪环的哌嗪类硫色满酮(图 1, D) [8] , 均表现 出较高的抗真菌活性, 部分化合物活性远远高于阳性对 照氟康唑.…”