Synthesis of DNA-directed pyrrolidinyl and piperidinyl confined alkylating chloroalkylaminoanthraquinones: Potential for development of tumor-selective N-oxides

Pors, Klaus, Shnyder, Steven D., Teesdale-Spittle, Paul H., Hartley, John A., Zloh, Mire, Searcey, Mark and Patterson, Laurence H. (2006) Synthesis of DNA-directed pyrrolidinyl and piperidinyl confined alkylating chloroalkylaminoanthraquinones: Potential for development of tumor-selective N-oxides. Journal of Medicinal Chemistry, 49 (24). pp. 7013-7023. ISSN 0022-2623

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Abstract

A novel series of 1,4-disubstituted chloroethylaminoanthraquinones, containing alkylating chloroethylamino functionalities as part of a rigid piperidinyl or pyrrolidinyl ring-system, have been prepared. The target compounds were prepared by ipso-displacement of halides of various anthraquinone chromophores by either hydroxylated or chlorinated piperidinyl- or pyrrolidinyl-alkylamino side chains. The chloroethylaminoanthraquinones were shown to alkylate guanine residues of linearized pBR322 (1-20 mu M), and two symmetrically 1,4-disubstituted anthraquinones (compounds 14 and 15) were shown to interstrand cross-link DNA in the low nM range. Several 1,4-disubstituted chloroethylaminoanthraquinones were potently cytotoxic (IC50 values:

Item Type: Article
Faculty \ School: Faculty of Science > School of Pharmacy
Depositing User: Rachel Smith
Date Deposited: 09 Jun 2011 11:24
Last Modified: 21 Apr 2020 19:50
URI: https://ueaeprints.uea.ac.uk/id/eprint/32087
DOI: 10.1021/jm0608154

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