ABSTRACT
Efficient access to evodiamine and its analogues is presented via Lewis acid catalysis. In this reaction, three chemical bonds and two heterocyclic-fused rings are constructed in one step. The reaction shows good functional group tolerance and atom economy, and various heteroatom-containing evodiamine analogues are obtained in moderate to excellent yields even on a gram scale. An anti-tumor study in vitro demonstrates compound 2b possesses potent efficacy against hepatoma cell line (IC50 = 5.7 µM).
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Evodia/chemistry , Quinazolines/chemistry , Quinazolines/pharmacology , Antineoplastic Agents, Phytogenic/chemical synthesis , Apoptosis/drug effects , Carcinoma, Hepatocellular/drug therapy , Cell Line, Tumor , Chemistry Techniques, Synthetic , Humans , Liver Neoplasms/drug therapy , Quinazolines/chemical synthesisABSTRACT
An efficient and practical methodology to obtain α-thio-ß-dicarbonyl compounds was presented under alkaline conditions via potassium iodide (KI) catalysis; various symmetrical/unsymmetrical 1,3-dicarbonyl compounds were obtained under an aerobic atmosphere in moderate to excellent yields, with good functional group tolerance. Notably, a widely used anti-inflammatory drug butazodine could be modified with our protocol, even on a gram scale.
ABSTRACT
An efficient, environmentally benign and unprecedented synthesis of various α-sulfenylated amides/esters has been developed under oxygen atmosphere. The reaction shows good functional group tolerance and excellent chemo/regioselectivity. All the desired products were obtained in moderate to excellent yields, even on the gram scale. Practically, the related α-thiol Weinreb amide can be readily transferred to a series of prospective compounds, and selenium atom can be introduced to the α-sites of the amides in high yields.
