- CYCLIC DINUCLEOTIDES AS ANTICANCER AGENTS
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The present invention is directed to compounds of the formula (I) wherein all substituents are defined herein, as well as pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.
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Page/Page column 84
(2019/05/10)
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- A practical synthesis of glycinamide ribonucleotide
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A practical nine-step synthesis of an alpha-/beta-anomeric mixture of glycinamide ribonucleotide (GAR) has been developed. The synthesis was accomplished in nine steps from D-ribose and occurred in 9.5% overall yield. The route as devised provided materia
- Ray, Debarpita,Beuning, Penny J.,Ondrechen, Mary Jo,O'Doherty, George A.
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p. 776 - 784
(2019/04/26)
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- Sequential Dy(OTf)3-Catalyzed Solvent-Free Per-O-Acetylation and Regioselective Anomeric De-O-Acetylation of Carbohydrates
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Dysprosium(III) trifluoromethanesulfonate-catalyzed per-O-acetylation and regioselective anomeric de-O-acetylation of carbohydrates can be tuned by adjusting the reaction medium. In this study, the per-O-acetylation of unprotected sugars by using a near-stoichiometric amount of acetic anhydride under solvent-free conditions resulted in the exclusive formation of acetylated saccharides as anomeric mixtures, whereas anomeric de-O-acetylation in methanol resulted in a moderate-to-excellent yield. Reactions with various unprotected monosaccharides or disaccharides followed by a semi-one-pot sequential conversion into the corresponding acetylated glycosyl hemiacetal also resulted in high yields. Furthermore, the obtained hemiacetals could be successfully transformed into trichloroimidates after Dy(OTf)3-catalyzed glycosylation.
- Yan, Yi-Ling,Guo, Jiun-Rung,Liang, Chien-Fu
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p. 2471 - 2479
(2017/09/06)
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- Synthesis of C -Ribosyl-1,2,3-triazolyl Carboxamides
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Because of the emergence of new viruses, the need for new antiviral broad-spectrum compounds remains important. In this context, herein the synthesis of C-nucleosides, structurally close to ribavirin, a nucleoside presenting various biological activities and used until now particularly for its broad-spectrum antiviral properties, is reported. The compounds were designed in order to increase their stability and the number of hydrogen bond donor or acceptor in comparison to ribavirin, and to investigate the role of the carboxamide group on the biological activity. The efficient synthesis of 11 C-nucleosides is based on an indium-mediated alkynylglycosylation as the key step, followed by the construction of the triazole heterocycle. Amidation was performed with primary and secondary amines in yields up to 85%. An analogue nucleoside with a triazole without carboxamide group was also prepared in order to compare its activity. Finally, the carboxamide group was moved to the N-1 triazole position to mimic ribavirin.
- Solarte, Carmen,Dos Santos, Micha?l,Gonzalez, Simon,Miranda, Leandro S. M.,Guillot, Régis,Ferry, Angélique,Gallier, Florian,Uziel, Jacques,Lubin-Germain, Nadège
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p. 1993 - 2002
(2017/04/26)
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- Functionalization of 2H-1,2,3-Triazole C-Nucleoside Template via N2 Selective Arylation
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C-Nucleosides are an underexplored and important class of nucleosides with antiviral and anticancer activity. In addition, triazole heterocycles are well employed as a strategy to modify nucleobase in nucleoside analogues, although rare examples were described for triazoyl C-nucleosides. N2-Aryl-1,2,3-triazole C-nucleoside compounds that could be obtained by selective 1,2,3-triazole heterocycle N2 arylation in 1-β-d-ribofuranosyl-2H-1,2,3-triazole substrate were designed in this study. The optimized condition used AdBrettPhos/[PdCl(allyl)]2 as the catalyst system. This transformation was accomplished by aryl halides bearing an electron donor and withdrawing groups, as well as by heterocyclic halides in good to excellent yields. The transformation developed in this study represents a significant contribution to the nucleoside field, once it allows for the synthesis of unexplored scaffolds through selective functionalization of triazole nucleosides.
- Lopes, Alexandra Basilio,Wagner, Patrick,De Souza, Rodrigo Octavio Mendon?a Alves,Germain, Nadège Lubin,Uziel, Jacques,Bourguignon, Jean-Jacques,Schmitt, Martine,Miranda, Leandro S. M.
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p. 4540 - 4549
(2016/07/06)
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- Total syntheses of the phytotoxic lactones herbarumin I and II and a synthesis-based solution of the pinolidoxin puzzle
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A concise approach to a family of potent herbicidal 10-membered lactones is described on the basis of ring-closing metathesis (RCM) as the key step for the formation of the medium-sized ring. This includes the first total syntheses of herbarumin I (1) and
- Fuerstner, Alois,Radkowski, Karin,Wirtz, Conny,Goddard, Richard,Lehmann, Christian W.,Mynott, Richard
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p. 7061 - 7069
(2007/10/03)
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- W-shape nucleic acid (WNA) for selective formation of non-natural anti-parallel triplex including a TA interrupting site
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Novel nucleoside analogs have been designed for selective formation of anti-parallel triplexes including a TA or a CG interrupting site. The new compounds are constructed of a W-shape bicyclic nucleic acid (WNA) bearing an aromatic ring as a stacking motif and a guanine for the formation of Hoogesteen hydrogen bonds, and are expected to effect triplex stabilization by both stacking and complementary hydrogen bonds. Purine-rich triplex-forming oligodeoxynucleotide (TFO) incorporating the new analog, WNA-7βG, formed a stable triplex with high selectivity to the TA site.
- Sasaki, Shigeki,Yamauchi, Hiroyuki,Nagatsugi, Fumi,Takahashi, Ryo,Taniguchi, Yosuke,Maeda, Minoru
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p. 6915 - 6918
(2007/10/03)
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