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Issue 10, 2019
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Synthesis and antitumor activities of aquayamycin and analogues of derhodinosylurdamycin A

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Abstract

Total syntheses of aquayamycin (3) and a number of analogues of angucycline antitumor antibiotic derhodinosylurdamycin A bearing various 2-deoxy sugar subunits (4–7) have been achieved. These molecules (3–7) were synthesized based on a convergent strategy for the synthesis of derhodinosylurdamycin A (2) previously reported from our group. In particular, our recently developed mild cationic gold-catalyzed glycosylation with S-but-3-ynyl thioglycoside donors was employed for the synthesis of analogues (6 and 7) bearing disaccharide subunits containing α-L-olivoside and α-L-olioside moiety, respectively. Aquayamycin (3), analogues (4–7), and our previously synthesized derhodinosylurdamycin A (2) were then submitted to the Development Therapeutics Program of the National Cancer Institute of National Institutes of Health for the NCI-60 Human Tumor Cell Lines Screening using standard protocols. It was found that derhodinosylurdamycin A (2), aquayamycin (3), and three other analogues (5–7) bearing sugar subunits did not show significant antiproliferative activity against those cancer cell lines. Interestingly, analogue (4) bearing no sugar subunit demonstrates good potential for growth inhibition and cytotoxic activity against a variety of human cancer cell lines.

Graphical abstract: Synthesis and antitumor activities of aquayamycin and analogues of derhodinosylurdamycin A

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Supplementary files

Article information


Submitted
16 Jan 2019
Accepted
08 Feb 2019
First published
08 Feb 2019

Org. Biomol. Chem., 2019,17, 2691-2704
Article type
Paper
Author version available

Synthesis and antitumor activities of aquayamycin and analogues of derhodinosylurdamycin A

P. P. Acharya, H. R. Khatri, S. Janda and J. Zhu, Org. Biomol. Chem., 2019, 17, 2691
DOI: 10.1039/C9OB00121B

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