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Hemi-phorboxazole a: structure confirmation, analogue design and biological evaluation.

ABSTRACT: A synthesis providing totally synthetic (+)-hemi-phorboxazole A (1), proceeding in two steps (85% yield) from known vinyl iodide precursor (+)-2, has been achieved in conjunction with the design, synthesis, and biological evaluation of two hemi-phorboxazole analogues [(+)-3 and (-)-4] featuring ring replacements inscribed within the macrolide. Although hemi-phorboxazole A (1) displayed no activity when tested against Candida albicans and two human cancer cell lines, analogue (-)-4 exhibited significant tumor cell growth inhibitory activity in the nanomolar range against HCT-116 (colon) and SK-BR-3 (breast), while (+)-3 displayed promising antifungal activity against C. albicans.

SUBMITTER: Smith AB

PROVIDER: S-EPMC2743491 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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Hemi-phorboxazole a: structure confirmation, analogue design and biological evaluation.

Smith Amos B AB Liu Zhuqing Z Hogan Anne-Marie L AM Dalisay Doralyn S DS Molinski Tadeusz F TF

Organic letters 20090801 16

A synthesis providing totally synthetic (+)-hemi-phorboxazole A (1), proceeding in two steps (85% yield) from known vinyl iodide precursor (+)-2, has been achieved in conjunction with the design, synthesis, and biological evaluation of two hemi-phorboxazole analogues [(+)-3 and (-)-4] featuring ring replacements inscribed within the macrolide. Although hemi-phorboxazole A (1) displayed no activity when tested against Candida albicans and two human cancer cell lines, analogue (-)-4 exhibited sign ...[more]

PMID: 19637861

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