Total synthesis and biological evaluation of clavaminol-G and its analogs.
Total synthesis and biological evaluation of clavaminol-G and its analogs.
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DOI：
10.1016/j.ejmech.2013.07.001
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发表时间：
2013-09
影响因子：
6.7
通讯作者：
T. V. Reddy;B.L.A. Prabhavathi Devi;R. Prasad;P. Sujitha;C. Kumar
中科院分区：
文献类型：
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作者：
T. V. Reddy;B.L.A. Prabhavathi Devi;R. Prasad;P. Sujitha;C. Kumar
以10-十一烯酸为原料，通过环氧化、区域选择性叠氮化、脱甲苯磺酰化和还原反应，首次实现了克拉氨基醇-G(1)和1-氨基十一烷-2-醇(2)的全合成。将该方法推广到1-氨基十一烷-2-醇衍生物的合成，即11-氨基-10-羟基十一酸甲酯(3)、11-氨基-10-羟基十一酸(4)和11-氨基十一烷-1，10-二醇(5)。其中，1-氨基十一烷-2-醇(2)对HeLa、Mda-MB-231、MCF7和A549细胞表现出良好的抗菌活性和良好的细胞毒性，IC50值分别为4.36、4.02、3.88和6.78gμM。化合物3对HeLa细胞表现出较好的抑制活性(IC_(50)=33.59μM)，化合物5对HeLa和A549细胞显示中等活性。Clavaminol G(1)和化合物4对所有的细胞系都没有活性。
The first total synthesis of clavaminol-G (1) and 1-aminoundecan-2-ol (2) has been achieved from 10-undecenoic acid using epoxidation, regioselective azidolysis andin situdetosylation and reduction reactions as key steps. The methodology is extended for the synthesis of 1-aminoundecan-2-ol derivatives; namely, methyl 11-amino-10-hydroxyundecanoate (3), 11-amino-10-hydroxyundecanoic acid (4) and 11-aminoundecan-1,10-diol (5). Among these, 1-aminoundecan-2-ol (2) exhibited good antimicrobial activity and promising cytotoxicity towards HeLa, MDA-MB-231, MCF-7 and A549 cell lines with IC50values of 4.36, 4.02, 3.88 and 6.78 μM, respectively. Compound3exhibited good activity against HeLa cells (IC50= 3.59 μM), while compound5showed moderate activity towards HeLa and A549 cell lines. Clavaminol G (1) and compound4showed no activity towards all the cell lines.