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A two-step, high yield, method for synthesizing naturally derived, Hemi-Phorboxazole A analogs
Problem:
(+)-Phorboxazole A and B, extracted from the sponge Phorbas sp., display extraordinary anti-proliferative activity against National Cancer Institute’s (NCI) panel of 60 human tumor cell lines. Due to their complex structures, the reported syntheses of Phorboxazole A and B analogues consist of 100 total steps with an average yield of 4%. The limited availability of these compounds has precluded the evaluation of their biological activity. As such, there is a need for improved syntheses of these compounds, featuring fewer steps while providing higher yield and selectivity.
Solution:
Researchers in the Smith Lab have developed a two-step, high yield (85%) method for preparing Hemi-Phorboxazole A from a known precursor. Two analogues of Hemi-Phorboxazole were designed and synthesized in this manner. One analogue exhibits anti-proliferation activities of human cancer cell lines HCT-116 (colon) and SPKB-3 (breast). Another analogue shows antifungal activity against Candida albicans.
Synthesis of completely synthetic (+)-hemi-phorboxazole A. From Smith AB et al, 2009.
Advantages:
Applications:
Stage of Development:
In vitro testing in human cell lines
Intellectual Property:
USSN 8,957,097
Reference Media:
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License
Docket # W5271
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