Unknown

Dataset Information

0

Phorboxazole Synthetic Studies: Design, Synthesis and Biological Evaluation of Phorboxazole A and Hemi-Phorboxazole A Related Analogues.


ABSTRACT: The design, synthesis and biological evaluation of a new phorboxazole analogue, comprising an acetal replacement for the C-ring tetrahdropyran of the natural product and carrying a potency-enhancing C(45-46) vinyl chloride side chain, is described. In addition, the synthesis of (+)-hemi-phorboxazole A and a series of related hemi-phorboxazole A analogues has been achieved. The new acetal ring replacement analogue displayed activity comparable to that of the parent natural product against HCT-116 (colon) cells (IC(50) 2.25 ng/mL). Equally important, the phorboxazole analogue and two related hemiphorboxazole A congeners exhibited significant antifungal activity when assayed against pathogenic Candida albicans strains.

SUBMITTER: Smith AB 

PROVIDER: S-EPMC3146768 | biostudies-literature | 2011 Jul

REPOSITORIES: biostudies-literature

altmetric image

Publications

Phorboxazole Synthetic Studies: Design, Synthesis and Biological Evaluation of Phorboxazole A and Hemi-Phorboxazole A Related Analogues.

Smith Amos B AB   Hogan Anne-Marie L AM   Liu Zhuqing Z   Razler Thomas M TM   Meis Regina M RM   Morinaka Brandon I BI   Molinski Tadeusz F TF  

Tetrahedron 20110701 27-28


The design, synthesis and biological evaluation of a new phorboxazole analogue, comprising an acetal replacement for the C-ring tetrahdropyran of the natural product and carrying a potency-enhancing C(45-46) vinyl chloride side chain, is described. In addition, the synthesis of (+)-hemi-phorboxazole A and a series of related hemi-phorboxazole A analogues has been achieved. The new acetal ring replacement analogue displayed activity comparable to that of the parent natural product against HCT-116  ...[more]

Similar Datasets

| S-EPMC6691772 | biostudies-literature
| S-EPMC2790820 | biostudies-literature
| S-EPMC2743491 | biostudies-literature
| S-EPMC6381151 | biostudies-literature
| S-EPMC9024523 | biostudies-literature
| S-EPMC8073777 | biostudies-literature
| S-EPMC5502735 | biostudies-literature
| S-EPMC2853872 | biostudies-literature
| S-EPMC9320607 | biostudies-literature
| S-EPMC4918913 | biostudies-literature