Synthesis of analogues of anthraquinones linked to tuftsin or retro-tuftsin residues as potential topoisomerase inhibitors

Abstract

A novel group of [(4-, 5- or 8)-hydroxy-9,10-anthraquinone-1-yl]-(tuftsin or retro-tuftsin) acids and methyl esters has been synthesized as potential anticancer compounds. The corresponding protected tuftsin or retro-tuftsin derivatives were also synthesized. We hope that combining compounds of different mechanisms of action will improve their clinical properties, and that our new analogues will be much more effective against multidrug-resistant tumour cell lines.

Evaluating the antibacterial activity of muramyl dipeptide derivatives, retro-tuftsin derivatives, and anthraquinone oligopeptides against a range of pathogenic bacteria

“…1) were selected and evaluated concerning their antimicrobial activity, i.e., muramyl dipeptide derivatives (1a-e), the retro-tuftsin derivatives (2a-c), and analogs of anthraquinones (3a-d). These compounds were previously published as potential immunomodulators by Dzierzbicka and others (Dzierzbicka et al, 2003b;Dzierzbicka et al, 2004;Dzierzbicka et al, 2005a;Dzierzbicka et al, 2005b;Dzierzbicka et al, 2006;Dzierzbicka et al, 2008;Dzierzbicka et al, 2012) and Wardowska and others (Wardowska et al, 2006;Wardowska et al, 2009). Their antimicrobial activities were tested against five bacterial strains from four species (S. aureus MRSA/MSSA, K. pneumoniae ESBL, P. aeruginosa, and E. coli), and their MIC values (and those of the reference antibiotics) are presented in Table 1.…”

“…1). The synthesis of test compounds has been described in our previous publications (Dzierzbicka et al, 2003b;Dzierzbicka et al, 2004;Dzierzbicka et al, 2005b;Dzierzbicka et al, 2006;Dzierzbicka et al, 2008;Dzierzbicka et al, 2012;Kukowska-Kaszuba et al, 2008), and herein, we investigate the antimicrobial activity of the three groups derivatives. It is possible that combining compounds showing different mechanisms of action may improve the clinical properties of both components; therefore, we propose that new analogues of anthraquinones, and muramyl dipeptide derivatives or retro-tuftsin derivatives will exhibit enhanced effectiveness against bacterial infections.…”

Influence of substituent on spectroscopic and acid-base properties of anthraquinone derivatives

“…All compounds were synthesized from 1,4-di-p-toluenosufonyloksy-9,10anthraquinone, obtained previously from 1,4-dihydroksy-9,10-anthraqinone [5,6]. The compounds (1), (2), (3) were prepared by the reaction of 1,4-di-p-toluenosufonyloksy-9,10-anthraquinone and excess of 2-(methylamino)ethanol, dimethylamine and diethylamine, in toluene in high temperature, obtaining 65%, 48%, and 72% yields for derivatives (1), (2), (3) respectively.…”

1,8-Bis(tosyloxy)-9,10-anthraquinone

“…This phenomenon is applicable to prepare the various aminoanthraquinone from (tosy1oxy)anthraquinone precursors (Zielske, 1987). The 1,8-Bis(tosyloxy)-9,10-anthraquinone is a very convenient and often used precursor to obtain the 1,8-diaminoanthraquinones derivatives (Dzierzbicka et al, 2006).…”