title: Highly regioselective synthesis of 3-alkenyl-oxindole ring-fused 3,3'-disubstituted oxindoles via direct gamma-substitution of Morita-Baylis-Hillman carbonates of isatins with 3-substituted oxindoles.
abstract: The first phase transfer-catalysed direct γ-substitution of Morita-Baylis-Hillman carbonates of isatins with 3-substituted oxindoles has been developed, which affords 3-alkenyl-oxindole ring-fused 3,3'-disubstituted oxindoles in up to 83% yield under mild reaction conditions. Furthermore, their biological activity has been preliminarily demonstrated by in vitro evaluation against human prostate cancer cells PC-3 and human leukemia cells K562, using MTT-based assays with the commercially available standard drug Cisplatin as a positive control. Gratifyingly, compounds 3aa, 3ba and 3ca exhibited comparable in vitro inhibitory activities against human prostate cancer cells (PC-3) to Cisplatin. What's more, 3ba also had a good inhibition ability against human leukemia cells K562. These results indicate that 3-alkenyl-oxindole ring-fused 3,3'-disubstituted oxindole analogs may be potential lead compounds for further biological screening.
authors.affiliation: Guizhou Engineering Center for Innovative Traditional Chinese Medicine and Ethnic Medicine, College of Pharmacy, Guizhou University, Guiyang, 550025, China. ls.liuxl@gzu.edu.cn yingzhou71@yeah.net.
authors.forename: Ting-Ting
authors.initials: TT
authors.lastname: Feng
authors.forename: Xuan
authors.initials: X
authors.lastname: Huang
authors.forename: Xiong-Li
authors.initials: XL
authors.lastname: Liu
authors.forename: De-Hong
authors.initials: DH
authors.lastname: Jing
authors.forename: Xiong-Wei
authors.initials: XW
authors.lastname: Liu
authors.forename: Feng-Ming
authors.initials: FM
authors.lastname: Guo
authors.forename: Ying
authors.initials: Y
authors.lastname: Zhou
authors.forename: Wei-Cheng
authors.initials: WC
authors.lastname: Yuan
mesh_terms: D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D002945:Cisplatin / Q000494:pharmacology; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D020014:K562 Cells; D008297:Male; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000498:Allyl Compounds; D000970:Antineoplastic Agents; D002254:Carbonates; D007211:Indoles; D002945:Cisplatin