- Regioselective Synthesis of a C-4′′ Carbamate, C-6′′ n-Pr Substituted Cyclitol Analogue of SL0101
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An asymmetric synthesis of two analogues of SL0101 (1) has been achieved. The effort is aimed at the discovery of inhibitors of the p90 ribosomal S6 kinase (RSK) with improved bioavailability. The route relies upon the use of the Taylor catalyst to regios
- Fukuda, Shinji,Lannigan, Deborah A.,Li, Mingzong,Li, Yu,O'Doherty, George A.,Sandusky, Zachary M.,Vemula, Rajender,Wu, Bulan,Zhang, Qi
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p. 1448 - 1452
(2020/03/13)
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- INFLUENCE OF RHAMNOSE SUBSTITUENTS ON THE POTENCY OF SL0101, AN INHIBITOR OF THE SER/THR KINASE, RSK
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The present invention provides compositions and methods useful for preparing and using analogs, derivatives, and modifications of kaempferols that have anti-neoplastic activity. More specifically, the compounds are analogs, derivatives, and modifications
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Page/Page column 37
(2008/06/13)
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- De novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation
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(Chemical Equation Presented) The enantioselective syntheses of naturally occurring kaempferol glycoside SL0101 (1a) and its analogues 1b-e, as well as their enantiomers, have been achieved in 7-10 steps. The routes rely upon a diastereoselective palladium-catalyzed glycosylation, ketone reduction, and dihydroxylation to introduce the rhamno-stereochemistry. The asymmetry of the sugar moiety of these kaempferol glycosides was derived from Noyori reduction of an acylfuran. An acetyl group shift from an axial (C-2) to equatorial position (C-3) under basic conditions was also described.
- Shan, Mingde,O'Doherty, George A.
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p. 5149 - 5152
(2007/10/03)
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- Influence of rhamnose substituents on the potency of SL0101, an inhibitor of the Ser/Thr kinase, RSK
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We have previously reported the isolation of kaempferol 3-O-(3″,4″-di-O-acetyl-α-l-rhamnopyranoside) from Forsteronia refracta [Xu, Y.-M.; Smith, J. A.; Lannigan, D. A.; Hecht, S. M. Biorg. Med. Chem. 2006, 14, 3974-3977.]. This flavonoid glycoside, terme
- Smith, Jeffrey A.,Maloney, David J.,Clark, David E.,Xu, Yaming,Hecht, Sidney M.,Lannigan, Deborah A.
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p. 6034 - 6042
(2007/10/03)
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