- Isosteres of ester derived glucose uptake inhibitors
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Glucose transporters (GLUTs) facilitate glucose uptake and are overexpressed in most cancer cells. Inhibition of glucose transport has been shown to be an effective method to slow the growth of cancer cells both in vitro and in vivo. We have previously reported on the anticancer activity of an ester derived glucose uptake inhibitor. Due to the hydrolytic instability of the ester linkage we have prepared a series of isosteres of the ester moiety. Of all of the isosteres prepared, the amine linkage showed the most promise. Several additional analogues of the amine-linked compounds were also prepared to improve the overall activity.
- Bergmeier, Stephen C.,Chen, Xiaozhuo,Liu, Yi,Qian, Yanrong,Roberts, Dennis A.,Shriwas, Pratik,Wang, Liyi,Zhang, Weihe
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- Synthesis of Fluorinated Derivatives of Benzofluoranthene and Indenopyrene and 8,9-dihydro-8,9-epoxybenzofluoranthene
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The synthesis of several select fluorinated derivatives of benzofluoranthene and indenopyrene is described.In the benzofluoranthene series, the 8- and 9-fluoro derivatives have been prepared by Wittig reaction of the 1,2-bis salt of the appropriate fluorobenzene with acenaphthenequinone under phase-transfer conditions.The synthesis of 2-fluoroindenopyrene was achieved by photocyclization of 1-(β,β-difluorovinyl)benzofluoranthene followed by dehydrofluorination in methanolic sodium methoxide.This represents a new method for the construction of the indenopyrene skeleton. 8,9-Difluoroindenopyrene was prepared from 1-(2-amino-4,5-diflurophenyl)pyrene by diazotization followed by coupling in the presence of copper-bronze.In addition to these fluorinated derivatives, the synthesis of 8,9-dihydro-8,9-epoxybenzofluoranthene, a suspect ultimate tumorigenic metabolite of benzofluoranthene, is reported.This arene oxide was prepared from the trans-8,9-bromo acetate by benzylic bromination and subsequent treatment with sodium methoxide in anhydrous THF.
- Rice, Joseph E.,Czech, Anna,Hussain, Nalband,LaVoie, Edmond J.
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p. 1775 - 1779
(2007/10/02)
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