16 research outputs found
SYNTHESIS OF 5-AZACYTOSINE 2’-DEOXYRIBONUCLEOSIDES, PROPERTIES AND BIOLOGICAL ACTIVITY
The effect of the o-D anomer Ia on L 1210 mouse leukemia cells was
studied. This nucleoside inhibited the cell growth in vitro (IC55 about
Lx 10-°m), and was also active in vivo in increasing the life span of
mice with L1210 leukemia (800 to 1000 mg/kg) by 100%. It is Supposed that
the action of the o-D anomer Ia is due to its conversion to Ib shown by
HPCL performed on water solutions of both anomers. Similarly, the conversion
of Ib to Ia was observed. Hydrolysis of 2'-deoxy-5-azacytidine (Ib)
or its «-D anomer Ia with aqueous ammonia affords N-amidino-N’-(2-deoxyß-
D-erythropentofuranosyl)urea formate (IVb). Cyclocondensation Of this
compound with dimethylformamide dimethyl acetal leads to a mixture of
anomeric nucleosides Ia and Ib. Stannic chloride catalysed condensation of
blocked 2-deoxy-D-ribopyranose with silylated 5-azacytosine and subsequent
methanolysis of the protected intermediates affords anomeric deoxyribopyranosyl
nucleoside Va and vb which do not exhibit biological extivity.
A series of 6-substituted deoxy nucleosides was prepared by direct glycosylation
and the isocyanate procedure. 6-Amino-2’-deoxy-5-azacytidine
prevents the growth of E. coli; the inhibition is completely reversed by
natural purine bases and/or nucleosides
Synthesis and Biological Study of the Cyclopentenyl Carbocyclic Nucleoside Analogue of 5-Azacytidine
Methyl 2-(5-chloro-1-methyl-2-oxo-2,3-dihydro-1H-indol-3-ylidene)acetate
The title compound, C12H10ClNO3, the indoline ring system is essentially planar, with a maximum deviation of 0.009 Å for the N atom. The indoline ring and acetate group are essentially coplanar, with a maximum deviation of 0.086 Å for the O atom. The mean plane through the methoxycarbonylmethyl group forms a dihedral angle of 3.68 (5)° with the plane of the indoline ring system. The molecular structure is stabilized by an intramolecular C—H...O hydrogen-bond interaction. In the crystal, π–π stacking interactions [centroid–centroid distance = 3.7677 (8) Å] occur between benzene rings, forming a chain running along the c-axis direction
Synthesis and antiviral evaluation of N-β-D-ribosides of ergot alkaloids
N-β-D-Ribosides of agroclavine (1), elymoclavine (2), lysergene (4), lysergol (3), and 9,10-dihydrolysergol (5) were prepared by SnCl2 catalyzed ribosylation of their TMS derivatives with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose. None of the new compounds exhibited activity against HIV or other viruses tested.status: publishe