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Hemi-Phorboxazole A: Structure Confirmation, Analogue Design and Biological Evaluation

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journal contribution
posted on 20.08.2009 by Amos B. Smith, Zhuqing Liu, Anne-Marie L. Hogan, Doralyn S. Dalisay, Tadeusz F. Molinski
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.

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