Title: Synthesis and cytotoxic properties of 4,11-bis[(aminoethyl)amino]anthra[2,3-b]thiophene-5,10-diones, novel analogues of antitumor anthracene-9,10-diones
Authors: Shchekotikhin, Andrey E ×
Glazunova, Valeria A
Dezhenkova, Lyubov G
Luzikov, Yuri N
Sinkevich, Yuri B
Kovalenko, Leonid V
Buyanov, Vladimir N
Balzarini, Jan
Huang, Fong-Chun
Lin, Jing-Jer
Huang, Hsu-Shan
Shtil, Alexander A
Preobrazhenskaya, Maria N #
Issue Date: Mar-2009
Publisher: Pergamon
Series Title: Bioorganic & Medicinal Chemistry vol:17 issue:5 pages:1861-1869
Abstract: We developed the synthesis of a series of thiophene-fused tetracyclic analogues of the antitumor drug ametantrone. The reactions included nucleophilic substitution of methoxy groups in 4,11-dimethoxyanthra[2,3-b] thiophene-5,10-diones with ethylenediamines, producing the derivatives of 4,11-diaminoanthra[2,3-b] thiophene-5,10-dione in good yields. Several compounds showed marked antiproliferative potency against doxorubicin-selected, P-glycoprotein-expressing tumor cells and p53 (-/-) cells. The cytotoxicity of some novel compounds for P-glycoprotein-positive cells is highly dependent on N-substituent at the terminal amino group of ethylenediamine moiety. The cytotoxic potency of selected compounds correlated with their ability to attenuate the functions of topoisomerase I and telomerase, strongly suggesting that these enzymes are the major targets of antitumor activity of anthra[2,3-b] thiophene-5,10-dione derivatives. (C) 2009 Elsevier Ltd. All rights reserved.
ISSN: 0968-0896
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

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