Synthesis and anticancer activity of sclerophytin-inspired hydroisobenzofurans
by Bateman, T. David; Joshi, Aarti L.; Moon, Kwangyul; Galitovskaya, Elena N.; Upreti, Meenakshi; Chambers, Timothy C.; McIntosh, Matthias C.
Three structurally related sets of hydroisobenzofuran analogs of sclerophytin A were prepared in three or four steps from (S)-(+)-carvone via an aldol-cycloaldol sequence. The most potent members of each set of analogs exhibited IC50's of 1-3 mu M in growth inhibitory assays against KB3 cells. The NCI 60-cell line 5-dose assay for analog 6h revealed a GI(50) = 0.148 mu M and LC50 = 9.36 mu M for the RPMI-8226 leukemia cell line, and a GI(50) = 0.552 mu M and LC50 = 26.8 mu M for the HOP-92 non-small cell lung cancer cell line.
- Journal
- Bioorganic and Medicinal Chemistry Letters
- Volume
- 19
- Issue
- 24
- Year
- 2009
- Start Page
- 6898-6901
- URL
- https://dx.doi.org/10.1016/j.bmcl.2009.10.079
- ISBN/ISSN
- 1464-3405; 0960-894X
- DOI
- 10.1016/j.bmcl.2009.10.079