- DDQ mediated regiospecific protection of primary alcohol and deprotection under neutral conditions: Application of new p-methoxy benzyl-pixyl ether as reagent of choice for nucleoside protection
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A simple and efficient protocol is described for regiosepecific protection of primary hydroxyl group both in nucleosides and other molecules with p-methoxy-benzyl 2,7-dimethyl pixylether (MBDPE) in presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). Furthermore, swift deprotection of 2, 7-dimethylpixyl (DMPx) is accomplished with DDQ in MeOH. Both procedures are successfully implemented on gram-scale synthesis of modified nucleosides. This protocol offers mild and neutral conditions for selective protection and deprotection of DMPx group while compatible in presence of other conventional protecting groups such as benzoyl, benzyl, THP, TBDPS and acetonide.
- Srishylam, Penjarla,Raji Reddy,Banerjee, Shyamapada,Penta, Santhosh,Sanghvi, Yogesh S.
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supporting information
p. 2588 - 2591
(2017/06/13)
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- Design and synthesis of α-carboxy phosphononucleosides
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Rhodium catalyzed O-H insertion reactions employing α- diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5′-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an α-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.
- Debarge, Sebastien,Balzarini, Jan,Maguire, Anita R.
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p. 105 - 126
(2011/04/17)
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- NOVEL MODULATORS OF CELL CYCLE CHECKPOINTS AND THEIR USE IN COMBINATION WITH CHECKPOINT KINASE INHIBITORS
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In its many embodiments, the present invention provides a novel class of pyrimidine analogs of formula (V) as targeted mechanism-based modulators of cell cycle checkpoints. Cancers and/or malignancies can be treated by administration of a cell cycle checkpoint modulator of the invention. Also discussed are suitable combinations of the cell cycle checkpoint modulator with a checkpoint kinase inhibitor to produce synergistic apoptosis in cancer cells. The invention includes methods of treating cancers by administering the combination of the cell cycle checkpoint modulator and the checkpoint kinase inhibitor, pharmaceutical compositions comprising the activator as well as the combination and pharmaceutical kits
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Page/Page column 94
(2009/06/27)
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- δ-Di-carboxybutyl phosphoramidate of 2′-deoxycytidine-5′-monophosphate as substrate for DNA polymerization by HIV-1 reverse transcriptase
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The replacement of the pyrophosphate moiety of 2′-deoxynucleoside triphosphates by non natural δ-dicarboxylic butyl amino acid allows incorporation of natural 2′-deoxycytidine into DNA using HIV-1 reverse transcriptase (RT) as enzyme. In contrast, the 3′-
- Zlatev, Ivan,Giraut, Anne,Morvan, Francois,Herdewijn, Piet,Vasseur, Jean-Jacques
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experimental part
p. 7008 - 7014
(2009/12/28)
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- INHIBITORS OF RNA DEPENDENT RNA POLYMERASE AND USES THEREOF
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The invention herein provides novel viral DNA polymerase compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with viral DNA polymerase activity, and processes and intermediates useful for preparing such compounds.
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- Nucleotide libraries as a source of biologically relevant chemical diversity: Solution-phase synthesis
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Solution-phase parallel synthesis of nucleotide library 1 consisting of 150 members is reported. (C) 2000 Elsevier Science Ltd. All rights reserved.
- Zhou, Wenqiang,Upendran, Sathya,Roland, Arlene,Jin, Yi,Iyer, Radhakrishnan P.
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p. 1249 - 1252
(2007/10/03)
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- Chemical Synthesis of the Pentadecadeoxyribonucleotide d(TTCTTCTACACACCC) by Improved Triester Approach
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The chemical synthesis of the pentadecanucleotide d(TTCTTCTACACACCC) by improved triester approach in solution with TPS/1-Methylimidazole as condensation agent is reported.Almost all condensation were complete within 5-10 minutes giving yields over 80 percent.All intermediate triester blocks showed purity degrees of higher than 90 percent after purification by simple silica gel chromatography.After deblocking the pentadecanucleotide was purified by DEAE-cellulose 52 chromatography and desalted, then showing 100 percent purity as seen by 20 percent polyacrylamide gel electrophoresis of the 5'-32P labeled oligonucleotide.The sequence of the synthetic oligomer was determined and confirmed by using the two-dimensional mobility shift method.The pentadecanucleotide was used as a hybridisation probe for cloned human insulin c-DNA.
- Rosenthal, A.,Cech, D.,Veiko, V. P.,Shabarova, Z. A.,Orezkaja, T. S.
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p. 764 - 773
(2007/10/02)
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