|Stereospecific synthesis of (-)-neplanocin F |
(Article) Publié: Nucleosides Nucleotides & Nucleic Acids, vol. 26 p.1111-1114 (2007)
The stereospecfic synthesis of (-)-neplanocin F was achieved in 15 steps from 2,3-O-isopropylidene-D-1,4-ribonolactone. The synthetic methodology can give an access through appropriate modifications to new series of carbanucleosides.
Commentaires: 244OO Times Cited:0 Cited References Count:6
|Revisited 3 '-deoxy-3 '-C-methyl-beta-D-ribonucleoside series |
(Article) Publié: Nucleosides Nucleotides & Nucleic Acids, vol. 26 (8-9) p.1125-1128 (2007)
The synthesis of some 3'-deoxy-3'-C-methylnucleoside analogues bearing naturally occuring nucleic acid bases was achieved from the preparation of a suitable peracylated 3-deoxy-3-C-methyl sugar using a stereoselective pathway. In addition, examples of chemical modifications at the 2' position are presented.
Commentaires: 2007 1525 7770 English
|L-Nucleoside enantiomers as antivirals drugs: A mini-review |
(Article) Publié: Antiviral Research, vol. 71 p.276-281 (2006)
The discovery that some nucleoside analogues endowed with the unnatural L-configuration can possess biological activities has been a significant breakthrough in antiviral chemotherapy. In this regard, lamivudine (3TC) was the first L-nucleoside enantiomer approved against HIV and HBV, and several other L-nucleosides are currently under clinical development as antiviral agents (c) 2006 Elsevier B.V. All rights reserved.
Commentaires: 082IY Times Cited:13 Cited References Count:41
|Synthesis and conformational analysis of C-4 '-modified (2-oxabicyclo-hexyl)pyrimidine nucleosides |
(Article) Publié: European Journal Of Organic Chemistry, vol. p.4891-4897 (2006)
We report on the synthesis of hitherto unknown pyrimidine nucleoside analogues bearing the 2-oxabicyclohexane scaffold (5, 6, 8, 13-17 and 19) with various modifications at the C-4' position including methylene, azido, and arabinolike configuration. Conformational analysis on the nucleoside analogues 6, 14 and 17 indicates that the conformation of such C-4'-modified nucleoside analogues was restricted in the South-East hemisphere of the pseudorotation cycle (between a T-0(1) and a E-2 conformation). ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).
Commentaires: 103TI Times Cited:3 Cited References Count:34
|Structure-activity relationships of uridine 5 '-diphosphate analogues at the human P2Y(6) receptor |
(Article) Publié: European Journal Of Medicinal Chemistry, vol. 49 p.5532-5543 (2006)
The structure-activity relationships and molecular modeling of the uracil nucleotide activated P2Y(6) receptor have been studied. Uridine 5'-diphosphate (UDP) analogues bearing substitutions of the ribose moiety, the uracil ring, and the diphosphate group were synthesized and assayed for activity at the human P2Y6 receptor. The uracil ring was modified at the 4 position, with the synthesis of 4-substituted-thiouridine 5'-diphosphate analogues, as well as at positions 2, 3, and 5. The effect of modifications at the level of the phosphate chain was studied by preparing a cyclic 3', 5'-diphosphate analogue, a 3'-diphosphate analogue, and several dinucleotide diphosphates. 5-Iodo-UDP 32 (EC50 = 0.15 mu M) was equipotent to UDP, while substitutions of the 2'-hydroxyl (amino, azido) greatly reduce potency. The 2-and 4-thio analogues, 20 and 21, respectively, were also relatively potent in comparison to UDP. However, most other modifications greatly reduced potency. Molecular modeling indicates that the beta-phosphate of 5'-UDP and analogues is essential for the establishment of electrostatic interactions with two of the three conserved cationic residues of the receptor. Among 4-thioether derivatives, a 4-ethylthio analogue 23 displayed an EC50 of 0.28 mu M, indicative of favorable interactions predicted for a small 4-alkylthio moiety with the aromatic ring of Y33 in TM1. The activity of analogue 19 in which the ribose was substituted with a 2-oxabicyclohexane ring in a rigid (S)-conformation (P = 126 degrees, 1'-exo) was consistent with molecular modeling. These results provide a better understanding of molecular recognition at the P2Y(6) receptor and will be helpful in designing selective and potent P2Y(6) receptor ligands.
Commentaires: 079AX Times Cited:7 Cited References Count:48