2009
DOI: 10.1016/j.bmc.2008.12.056
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Design, synthesis and biological evaluation of a novel class of anticancer agents: Anthracenylisoxazole lexitropsin conjugates

Abstract: The synthesis and in vitro anti-tumor 60 cell lines screen of a novel series of anthracenyl isoxazole amides (AIMs)¥ (22-33) is described. The molecules consist of an isoxazole that pre-organizes a planar aromatic moiety and a simple amide and/or lexitropsin-oligopeptide. The new conjugate molecules were prepared via doubly activated amidation modification of Weinreb's amide formation technique, using SmCl 3 as an activating agent which produces improved yields for sterically hindered 3-aryl-4-isoxazolecarboxy… Show more

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Cited by 30 publications
(32 citation statements)
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“…5 The existence of a safe route for drug metabolism is an important design feature for potential investigational new drugs containing the isoxazole. Our own interest in the biological activity of several classes of isoxazoles [6][7][8] required access into isoxazole carbinols in chiral form for metabolic fate experiments.…”
Section: Introductionmentioning
confidence: 99%
“…5 The existence of a safe route for drug metabolism is an important design feature for potential investigational new drugs containing the isoxazole. Our own interest in the biological activity of several classes of isoxazoles [6][7][8] required access into isoxazole carbinols in chiral form for metabolic fate experiments.…”
Section: Introductionmentioning
confidence: 99%
“…Techniques using fluorescent compounds in the visualization of tumors during surgery, referred to as tumor paint, are actively being developed. 24 We have recently reported on the synthesis, bioactivity and structure-activity relationship (SAR) of fluorescent anthracenyl isoxazole amides (AIMs, 1 ), 5 as well as their dimeric analogues ( 2 ) 6 depicted in Chart 1. The AIMs have shown promising activity in the National Cancer Institute’s 60-cell line screening protocol (NCI 60) and could be exploited for tumor imaging.…”
mentioning
confidence: 99%
“…11 The acyl chlorides were then condensed with the bis-dimethylamino propyl pyrrole amine 6,11,12 under modified Schotten-Baumann conditions (Scheme 1 and Supplementary Data). Purification was accomplished via preparative TLC on silica gel eluting with 10% ammonium hydroxide in methanol.…”
mentioning
confidence: 99%
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“…[25][26][27][28][29] The extraordinary biological and synthetic significance of compounds of the pyrrole series is a powerful stimulus to motivation the development of new approaches to the synthesis of these compounds. [30][31][32][33][34] In this paper we present novel results of our investigations of the nitropyridinium salt rearrangement to 2-acyl-4-nitropyrroles.…”
mentioning
confidence: 99%