4-烷基取代溴代呋喃酮合成及其对铜绿假单胞菌生物膜形成的抑制作用

Synthesis of 4-alkyled bromated 2(5H)-furanones and its inhibition to Pseudomonas aeruginosa biofilm

以不同烷基取代丙酮和乙醛酸在酸性条件下缩合成3-烷基-4-氧代-2-戊烯酸,再通过选择性还原双键,二溴海因(DBDMH)作为溴代试剂对酮羰基α-位进行溴代,以及P2O5催化成呋喃酮环,共合成了14个3-位不同取代基的两个系列溴代呋喃酮,其结构经NMR和MS表征。初步生物活性测试结果显示A5、B5和G5对铜绿假单胞菌生物膜的形成具有较好的抑制作用,并且A5-G5系列的单溴代亚甲基呋喃酮的活性优于A4-G4系列的二溴亚甲基呋喃酮。

The 3-alkyl-4-oxo-2-pentenoic acids were synthesized with diverse alkyl substituted acetone and glyoxalic acid as the starting materials under acidic conditions. Fourteen target compounds were synthesized via selectively reducing C--C double bond, bromating at a-position of carbonyl bond by DBDMH as a bromide reagent and finally ring closure as furanones by using P205. All the compounds were identified by NMR and MS. The preliminary bioassay tests indicated that compounds AS, B5 and G5 showed remarkable effects on biofilm inhibition of Pseudomonas aeruginosa, and AS-G5 compounds were verified more efficacious than that of A4-G4.