ChemInform Abstract: DETERMINATION OF THE ANOMERIC CONFIGURATION OF C‐NUCLEOSIDES BY PROTON AND CARBON‐13 NMR SPECTROSCOPY

Chu, C. K.; El-Kabbani, F. M.; Thompson, B. Blackburn

doi:10.1002/chin.198536356

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“…(-)-[2S(2a,5a)]-2-[[(tert-Butyldiphenylsilyl)oxy]methyl]-1.3-oxathiolane-5-methanol (20). NaOMe (0.33 g, 0.0061 mol) was added to a solution of 19 (15 g, 0.0305 mol) in MeOH (30 mL) and the reaction mixture stirred at room temperature for 2 h. After the mixture was neutralized with glacial acetic acid, MeOH was removed under high vacuum and the residue dissolved in ethyl acetate (350 mL), washed with water (200 mL) and brine (100 mL), dried (MgS04), and evaporated.…”

Section: -)-[2s[2a(jz)5e]]-l-[2-[[(tert-butyidiphenylsilyimentioning

confidence: 99%

Structure-activity relationships of .beta.-D-(2S,5R)- and .alpha.-D-(2S,5S)-1,3-oxathiolanyl nucleosides as potential anti-HIV agents

Jeong

Schinazi²,

Beach³

et al. 1993

J. Med. Chem.

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The beta-D-(2S,5R)- and alpha-D-(2S,5S)-1,3-oxathiolanylpyrimidine and -purine nucleosides with natural nucleoside configuration were synthesized and evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells. The key intermediate 14, which was utilized for the synthesis of various nucleosides, was synthesized from D-mannose or D-galactose. Condensation of the acetate 14 with thymine, uracil, cytosine, and 5-substituted uracils and cytosines gave various pyrimidine nucleosides. The acetate 14 was also condensed with 6-chloropurine and 6-chloro-2-fluoropurine which were converted to various purine nucleosides. In the case of thymine, uracil, and 5-substituted uracil derivatives, most of the compounds did not exhibit any significant anti-HIV activity except 5-fluorouracil (alpha-isomer) derivative 55. Among 5-substituted cytosine analogues, 5-bromocytosine derivative (beta-isomer) 68 was found to be the most potent anti-HIV agent. In the case of purine derivatives, inosine analogue (beta-isomer) 78 was found to be the most potent anti-HIV agent in the 6-substituted purines and 2-amino-6-chloropurine derivative (beta-isomer) 90 showed the most potent activity in the 2,6-disubstituted purine series. The beta-isomers of 6-chloropurine (74), adenine (76), and N6-methyladenine (77) derivatives showed similar potencies against HIV-1, and the corresponding alpha-isomers also exhibited significant anti-HIV activity, although they were generally less potent than the beta-isomers.

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Section: -)-[2s[2a(jz)5e]]-l-[2-[[(tert-butyidiphenylsilyimentioning

confidence: 99%