Efficient synthesis and biological activity of Psammaplin A and its analogues as antitumor agents SCIE SCOPUS

Cited 22 time in WEB OF SCIENCE Cited 23 time in Scopus
Title
Efficient synthesis and biological activity of Psammaplin A and its analogues as antitumor agents
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)
Publication Year
2015-05-26
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.
ISSN
0223-5234
URI
https://sciwatch.kiost.ac.kr/handle/2020.kiost/2485
DOI
10.1016/j.ejmech.2015.04.001
Bibliographic Citation
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, v.96, pp.218 - 230, 2015
Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
Subject
HISTONE DEACETYLASE INHIBITORS; RESISTANT STAPHYLOCOCCUS-AUREUS; NATURAL-PRODUCT PSAMMAPLIN; CANCER-CELLS; HDAC INHIBITORS; SPONGE; METABOLITES; DISCOVERY; APOPTOSIS; MRSA
Keywords
Psammaplin A; Structure-activity relationship; HDAC; Histone deacetylase inhibitor
Type
Article
Language
English
Document Type
Article
Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
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