Hemi-phorboxazole a: structure confirmation, analogue design and biological evaluation.
Hemi-phorboxazole a: structure confirmation, analogue design and biological evaluation.
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半佛波唑a：结构确认、类似物设计和生物学评价。
DOI：
10.1021/ol9014317
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发表时间：
2009
期刊：
影响因子：
5.2
通讯作者：
Molinski,TadeuszF
中科院分区：
文献类型：
--
作者：
Smith3rd,AmosB;Liu,Zhuqing;Hogan,Anne-MarieL;Dalisay,DoralynS;Molinski,TadeuszF
由已知的乙烯基碘前体（+）-2以两个步骤（85%产率）进行的提供完全合成的（+）-半-苯并恶唑A（1）的合成，已经与两种半-苯并恶唑类似物[（+）-3和（-）-4]的设计、合成和生物学评价结合实现，所述半-苯并恶唑类似物[（+）-3和（-）-4]的特征在于在大环内酯内的环置换。尽管半恶唑A（1）在对白色念珠菌和两种人类癌细胞系进行测试时没有显示出活性，但类似物（-）-4在纳摩尔范围内对HCT-116（结肠）和SK-BR-3（乳腺）表现出显著的肿瘤细胞生长抑制活性，而（+）-3对C显示出有希望的抗真菌活性。白色念珠菌。
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 [(+)-3and (−)-4] featuring ring replacements inscribed within the macrolide. Although hemi-phorboxazole A (1) displayed no activity when tested againstCandida albicansand two human cancer cell lines, analogue (−)-4exhibited significant tumor cell growth inhibitory activity in the nanomolar range against HCT-116 (colon) and SK-BR-3 (breast), while (+)-3displayed promising antifungal activity againstC. albicans.