Efficient synthesis and biological activity of Psammaplin A and its analogues as antitumor agents
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Title
- Efficient synthesis and biological activity of Psammaplin A and its analogues as antitumor agents
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Author(s)
- Hong, Suckchang; Shin, Yoonho; Jung, Myunggi; Ha, Min Woo; Park, Yohan; Lee, Yeon-Ju; Shin, Jongheon; Oh, Ki Bong; Lee, Sang Kook; Park, Hyeung-geun
- KIOST Author(s)
- Lee, Yeon Ju(이연주)
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Alternative Author(s)
- 이연주
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Publication Year
- 2015-05-26
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Abstract
- We describe a new concise method for the synthesis of psammaplin A and its analogues, and antitumor activity of psammaplin A analogues. Psammaplin A was obtained with 41% yield in 5 steps from 3-bromo-4-hydroxybenzaldahyde and ethyl acetoacetate via Knoevenagel condensation and alpha-nitrocation as key steps. Twenty eight analogues of psammaplin A were prepared employing the new synthetic approach. Structure-activity relationship study against cytotoxicity reveal that the free oxime group and disulfide functional group were responsible for high cytotoxicity. Also the bromotyrosine component was relatively tolerable and hydrophobic aromatic groups preserved the cytotoxicity. The cytotoxicity of aromatic group is dependent on the size and spatial geometry. Among them, five compounds showed comparable cytotoxicity to psammaplin A. Compound 30 exhibited potential HDAC inhibitory activity and in vivo antitumor activity. (C) 2015 Elsevier Masson SAS. All rights reserved.
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ISSN
- 0223-5234
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URI
- https://sciwatch.kiost.ac.kr/handle/2020.kiost/2485
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DOI
- 10.1016/j.ejmech.2015.04.001
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Bibliographic Citation
- EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, v.96, pp.218 - 230, 2015
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Publisher
- ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
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Subject
- HISTONE DEACETYLASE INHIBITORS; RESISTANT STAPHYLOCOCCUS-AUREUS; NATURAL-PRODUCT PSAMMAPLIN; CANCER-CELLS; HDAC INHIBITORS; SPONGE; METABOLITES; DISCOVERY; APOPTOSIS; MRSA
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Keywords
- Psammaplin A; Structure-activity relationship; HDAC; Histone deacetylase inhibitor
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Type
- Article
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Language
- English
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Document Type
- Article
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