74427-40-0Relevant articles and documents
Three lysocolorimetric/lysofluorescent probes with mitochondria/lysosome dual targeting positioning
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Paragraph 0050-0051, (2021/05/01)
The invention discloses a preparation method of three lysocolorimetric/lysofluorescent probes with mitochondria/lysosome dual targeting positioning and application thereof in biological imaging, which belong to the technical field of chemical analysis and detection. The structure and the detection mechanism of the lysocolorimetric/lysofluorescent probes are as follows: the probes prepared have stronger solvent-induced discoloration characteristics, and the fluorescent quantum yield is relatively high. Cell experiments show that the prepared probe has a good mitochondria/lysosome positioning effect.
Synthesis and pharmacological evaluation of carboxycoumarins as a new antitumor treatment targeting lactate transport in cancer cells
Draoui, Nihed,Schicke, Olivier,Fernandes, Antony,Drozak, Xavier,Nahra, Fady,Dumont, Amélie,Douxfils, Jonathan,Hermans, Emmanuel,Dogné, Jean-Michel,Corbau, Romu,Marchand, Arnaud,Chaltin, Patrick,Sonveaux, Pierre,Feron, Olivier,Riant, Olivier
, p. 7107 - 7117 (2013/11/06)
Under hypoxia, cancer cells consume glucose and release lactate at a high rate. Lactate was recently documented to be recaptured by oxygenated cancer cells to fuel the TCA cycle and thereby to support tumor growth. Monocarboxylate transporters (MCT) are the main lactate carriers and therefore represent potential therapeutic targets to limit cancer progression. In this study, we have developed and implemented a stepwise in vitro screening procedure on human cancer cells to identify new potent MCT inhibitors. Various 7-substituted carboxycoumarins and quinolinone derivatives were synthesized and pharmacologically evaluated. Most active compounds were obtained using a palladium-catalyzed Buchwald-Hartwig type coupling reaction, which proved to be a quick and efficient method to obtain aminocarboxycoumarin derivatives. Inhibition of lactate flux revealed that the most active compound 19 (IC 50 11 nM) was three log orders more active than the CHC reference compound. Comparison with warfarin, a conventional anticoagulant coumarin, further showed that compound 19 did not influence the prothrombin time which, together with a good in vitro ADME profile, supports the potential of this new family of compounds to act as anticancer drugs through inhibition of lactate flux.
Effect of Different Dialkylamino Groups on the Regioselectivity of Lithiation of O-Protected 3-(Dialkylamino)phenols
Skowronska-Ptasinska, Maria,Verboom, Willem,Reinhoudt, David N.
, p. 2690 - 2698 (2007/10/02)
The lithiation of 3-(dialkylamino)phenols (dialkylamino = 1-pyrrolidynyl, 1-piperidinyl, 4-morpholinyl, and dimethylamino) O-protected by a methyl, a methoxymethyl, or a carbamoyl group (X) has been studied.The results demonstrate that the site of lithiation depends on the relative ortho-directing capacities of both the dominant OX and the dialkylamino groups.With the moderate ortho-directing methoxy group the lithiation occurs exclusively (1b and 1c) or predominantly (1a) ortho to both substituents.The site of lithiation of the N,N-dialkyl-3-(methoxymethoxy)anilines 4a-c depends on the solvent used and on the type of dialkylamino group.With a strong ortho-directing group such as carbamoyloxy (9a,b,d) the lithiation takes place at the least hindered ortho position.In the absence of an electrophile the lithiated carbamates 9a,d and 10a,d rearrange stereospecifically to the corresponding benzamides 13a,d and 14a,d, respectively.
