Natural tanshinone-like heterocyclic-fused ortho-quinones from regioselective Diels-Alder reaction: synthesis and cytotoxicity evaluation.
A series of new natural tanshinone-like oxoheterocyclic-fused ortho-quinone derivatives were synthesized from readily available benzofuranol and N-substituted dienes via IBX oxidation-cycloaddition-aromatization procedure. The regiospecific Diels-Alder cycloaddition reactions of N-dienes were achieved efficiently with a variety of dienophiles. It is found that the amide moiety in the molecular could be preserved or eliminated by control of the aromatization conditions. Selected oxoheterocyclic-fused ortho-quinones as well as several thioheterocyclic-fused ortho-quinones we obtained before were evaluated for their cytotoxicities on different cancer cell lines and the Structure-Activity Relationship (SAR) was discussed.
College of Food Science, South China Agricultural University, Guangzhou 510642, China.
Yu-Dong
YD
Shen
Yuan-Xin
YX
Tian
Xian-Zhang
XZ
Bu
Lian-Quan
LQ
Gu
D000230:Adenocarcinoma / Q000188:drug therapy; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D002277:Carcinoma / Q000188:drug therapy; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D006801:Humans; D008175:Lung Neoplasms / Q000188:drug therapy; D008958:Models, Molecular; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D009303:Nasopharyngeal Neoplasms / Q000188:drug therapy; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D005663:Furans; D009285:Naphthoquinones