7387-57-7Relevant academic research and scientific papers
Selective Acylation of Nucleosides, Nucleotides, and Glycerol-3-phosphocholine in Water
Fernández-García, Christian,Powner, Matthew W.
supporting information, p. 78 - 83 (2016/12/26)
A convenient selective synthesis of 2′,3′-di-O-acetyl-nucleotide-5′-phosphates, 2′,3′-di-O-acetyl-nucleotide-5′-triphosphates and 2′,3′,5′-tri-O-acetyl-nucleosides in water has been developed. Furthermore, a long-chain selective glycerol-3-phosphocholine diacylation is elucidated. These reactions are environmentally benign, rapid, high yielding, and the products are readily purified. Importantly, this reaction may indicate a prebiotically plausible reaction pathway for the selective acylation of key metabolites to facilitate their incorporation into protometabolism.
Efficient and green approach for the complete deprotection of O-acetylated biomolecules
Dunne, Anthony,Palomo, Jose M.
, p. 88974 - 88978 (2016/10/03)
A simple, efficient and mild strategy for the complete O-deacetylation of different per-acetylated biomolecules in aqueous media has been described. Different lipases were tested but only the commercial Amano lipase A from Aspergillus Niger catalyzed the complete deprotection of peracetylated α-glucose to glucose in excellent yield. The experimental conditions were tested, in particular the pH effect. The reaction was performed at different pHs considering the only enzymatic process was evaluated at pH 5 and the combination of enzymatic and chemical migration process was evaluated at higher pHs. Finally pH 7 and 25 °C were selected as best conditions. Thus this lipase fully hydrolyzed different peracetylated α-glycopyranosides (glucose, mannose, glucal, galactal) with >99% yields, whereas very good deprotecting yields (75-80%) were achieved for different acetylated β-glycopyranosides (galactose, ribofuranose) under these mild conditions. This strategy was successfully extended to the fully O-selective deprotection of acetylated nucleosides where >99% yield was rapidly obtained. No selectivity was observed for the N-deacetylation in amino acids and peptides.
Stability studies on the newly discovered cyclic form of tRNA N 6-threonylcarbamoyladenosine (ct6A)
Matuszewski, Michal,Sochacka, Elzbieta
supporting information, p. 2703 - 2706 (2014/06/09)
A cyclic form of N6-threonylcarbamoyladenosine bearing an oxazolone moiety (ct6A) was discovered very recently at the position 37 in several tRNA sequences. Our study on the synthesized 5′,3′, 2′-O-acetylated derivative of ct6A confirmed high stability of the modified nucleoside under physiological conditions (PBS buffer, pH 7.4) and revealed remarkable stability of the oxazolone ring in acidic (100 mM HCl, pH 1) and basic (0.1 mM NaOH, pH 10) conditions. This feature may allow for the post-synthetic conversion of t6A into ct6A in assembled oligoribonucleotides.
Synthesis of purine and 7-deazapurine nucleoside analogues of 6-N-(4-nitrobenzyl)adenosine; Inhibition of nucleoside transport and proliferation of cancer cells
Rayala, Ramanjaneyulu,Theard, Patricia,Ortiz, Heysell,Yao, Sylvia,Young, James D.,Balzarini, Jan,Robins, Morris J.,Wnuk, Stanislaw F.
, p. 2186 - 2192 (2014/11/07)
Human equilibrative nucleoside transporter 1 (hENT1) is a prototypical nucleoside transporter protein ubiquitously expressed on the cell surface of almost all human tissue. Given the role of hENT1 in the transport of nucleoside drugs, an important class of therapeutics in the treatment of various cancers and viral infections, efforts have been made to better understand the mechanisms by which hENT1 modulates nucleoside transport. To that end, we report here the design and synthesis of novel tool compounds for the further study of hENT1. The 7-deazapurine nucleoside antibiotic tubercidin was converted into its 4-N-benzyl and 4-N-(4-nitrobenzyl) derivatives by alkylation at N3 followed by a Dimroth rearrangement to the 4-N-isomer or by fluoro-diazotization followed by SNAr displacement of the 4-fluoro group by a benzylamine. The 4-N-(4-nitrobenzyl) derivatives of sangivamycin and toyocamycin antibiotics were prepared by the alkylation approach. Cross-membrane transport of labeled uridine by hENT1 was inhibited to a weaker extent by the 4-nitrobenzylated tubercidin and sangivamycin analogues than was observed with 6-N-(4-nitrobenzyl)adenosine. Type-specific inhibition of cancer cell proliferation was observed at micromolar concentrations with the 4-N-(4-nitrobenzyl) derivatives of sangivamycin and toyocamycin, and also with 4-N-benzyltubercidin. Treatment of 2′,3′,5′-O-acetyladenosine with aryl isocyanates gave the 6-ureido derivatives but none of them exhibited inhibitory activity against cancer cell proliferation or hENT1.
Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO4 in water
Xia, Ran,Xie, Ming-Sheng,Niu, Hong-Ying,Qu, Gui-Rong,Guo, Hai-Ming
, p. 1077 - 1081 (2014/03/21)
A simple dehydrazination reaction has been achieved in the presence of a catalytic amount of CuSO4 for the first time. With CuSO4 (2 mol%) as a catalyst and water as a solvent, the dehydrazination products were obtained in good yields (66-95%). Moreover, the drugs nebularine and vidarabine were afforded successfully, and vidarabine could be produced on a 0.923 kg scale, which shows good potential for industrial applications.
A versatile synthesis of 5'-fenctionalized nucleosides through regioselective enzymatic hydrolysis of their peracetylated precursors
Bavaro, Teodora,Rocchietti, Silvia,Ubiali,Filice, Marco,Terreni, Marco,Pregnolato, Massimo
experimental part, p. 1967 - 1975 (2009/09/08)
We describe a chemo-enzymatic synthesis of modified nucleosides through lipase-catalyzed hydrolysis of their peracetylated precursors. It was found from screening of a large number of substrates that these enzymesregioselectivities were affected by the sugar and the nucleobase structures. By selecting the best enzyme for each substrate in terms of activity and regioselectivity, we prepared a small library of differently monodeprotecled purine and pyrimidine nucleosides useful as intermediates for the synthesis of high-value nucleosides and mononucleotides. By this approach, the chemo-enzymatic preparation of doxifluridine (14) and uridine 5'-monophosphate (5'-UMP, 15) from peracetylated uridine 1 was carried out. Elimination of many of the processing stages associated with existing methods was achieved, and higher yields and products of increased purity were generated. Wiley-VCH Verlag GmbH & Co. KGaA.
Synthesis of guanosine 5′-conjugates and their use as initiator molecules for transcription priming
Wolf, Joern,Dombos, Valeska,Appel, Bettina,Mueller, Sabine
supporting information; experimental part, p. 899 - 907 (2008/10/09)
We have synthesised two guanosine derivatives that are linked to biotinylated adenosine moieties by using two different strategies, one that includes synthetic steps on the solid phase and another one that is performed entirely in solution. The synthesised derivatives were shown to function as initiator molecules in transcription priming experiments. The incorporation efficiency was determined to be approximately 2%. Even though this value is rather low, the use of either molecule in selection experiments seems reasonable. Basically, RNA libraries with sequence complexities of 10 15 to 1016 can be generated. Labelling of such a library with our initiator molecule would still produce 1013 to 10 14 labelled/functionalised sequences, and thus sufficient sequence space for selection. The Royal Society of Chemistry.
COMPOUND HAVING INHIBITORY ACTIVITY ON A RHO-GTPASE CELL PROTEIN, A PROCESS FOR OBTAINING THE SAME, PHARMACEUTICAL COMPOSITIONS COMPRISION THEREOF AND A METHOD FOR THE TREATMENT OF A RHO-GTPASE CELL PROTEIN-MEDIATED CONDITION
-
Page/Page column 25-26, (2008/12/05)
The present invention relates to a compound having inhibitory activity on a Rho-GTPase cell protein, the compound having the formula I (Formula I ) wherein A is selected from N and N-H, R1 is selected from H and NHR3, R2 is selected from NHR4, OR4, O and halogen, R3 is selected from H and -COR5, R4 is selected from H, a C1-C6 alkyl and a substituted or unsubstituted phenyl, R5 is selected from a C1-C12 alkyl and a substituted or unsubstituted phenyl, R6 is selected from H, -COR5, -CO2R5, -PR7R8 and -PR7R8OPR7R8R8R7, R7 is selected from O and S, R8 is selected from H, OR4 and OSATE (-OCH2CH2SCOR5), and wherein each represents a single bond or a double bond, provided that when one of them is a double bond the other one is a single bond, and pharmaceutically acceptable salts and derivatives thereof. In particular, the compounds of the invention may be used as antitumor agents the action of which interfere with the signaling pathways normally involved in tumor development processes. The invention also relates to processes for obtaining of compounds having inhibitory activity of a Rho- GTPase cell protein, to the pharmaceutical compositions thereof and to the therapeutic methods comprising the use of said compounds and compositions.
Spectral assignments and reference data complete1H and 13C NMR spectral assignment of α- And β-adenosine, 2′-deoxyadenosine and their acetate derivatives
Ciuffreda,Casati,Manzocohi
, p. 781 - 784 (2008/03/17)
1H and 13C NMR chemical shifts of α- and β-anomers of adenosine, 2′-deoxyadenosine and their acetate derivatives were completely and definitely assigned using the concerted application of one- and two-dimensional experiments (gCOSY, gNOESY, gHSQC and gHMBC). The influence of the stereochemistry of the purine base on the NMR data of the hydrogen and carbon atoms of the furanose moiety was estimated. Copyright
Synthesis and enzymic hydrolysis of acylated adenosine derivatives
Car,Petrovic,Tomic
, p. 713 - 723 (2007/10/03)
Various derivatives of adenosine were prepared by acylation of adenosine (6-amino-9-(β-D-ribofuranosyl)purine (1) with different molar equivalents of acetic anhydride and/or pivaloyl chloride in pyridine. Compounds 6-acetylamino-9-[(2,3,5-tri-O-acetyl)-β-D-ribofuranosyl]purine (3), 6-amino-9-[(2,3,5-tri-O-acetyl)-β-D-ribofuranosyl]purine (4), and 6-pivaloylamino-9-[(2,3,5-tri-O-pivaloyl)-β-D-ribofuranosyl]purine (5) were subsequently submitted to hydrolysis catalyzed by a number of hydrolytic enzymes. Regioselective enzymic deacetylation at the primary hydroxyl group of 3 and 4 with butyrylcholinesterase (BChE) produced 6-acetylamino-9-[(2,3-di-O- acetyl)-β-D-ribofuranosyl]purine (9) and 6-amino-9-[(2,3-di-O-acetyl- β-D-ribofuranosyl]purine (10), respectively. All structures were established by 1H and 13C NMR spectroscopies.
