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Synthesis and anticancer activity of sclerophytin-inspired hydroisobenzofurans.

ABSTRACT: 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 IC(50)'s of 1-3 microM in growth inhibitory assays against KB3 cells. The NCI 60-cell line 5-dose assay for analog 6h revealed a GI(50)=0.148 microM and LC(50)=9.36 microM for the RPMI-8226 leukemia cell line, and a GI(50)=0.552 microM and LC(50)=26.8 microM for the HOP-92 non-small cell lung cancer cell line.

SUBMITTER: Bateman TD

PROVIDER: S-EPMC3276365 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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Synthesis and anticancer activity of sclerophytin-inspired hydroisobenzofurans.

Bateman T David TD Joshi Aarti L AL Moon Kwangyul K Galitovskaya Elena N EN Upreti Meenakshi M Chambers Timothy C TC McIntosh Matthias C MC

Bioorganic & medicinal chemistry letters 20091022 24

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 IC(50)'s of 1-3 microM in growth inhibitory assays against KB3 cells. The NCI 60-cell line 5-dose assay for analog 6h revealed a GI(50)=0.148 microM and LC(50)=9.36 microM for the RPMI-8226 leukemia cell line, and a GI(50)=0.552 microM and LC(50)=26.8 microM for the HOP- ...[more]

PMID: 19896844

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