99614-77-4

Usage

InChI:InChI=1/C10H13N5O5/c1-4-2-15(10(19)12-8(4)18)9-7(17)6(13-14-11)5(3-16)20-9/h2,5-7,9,16-17H,3H2,1H3,(H,12,18,19)/t5-,6-,7+,9-/m1/s1

Upstream product

• 128269-50-1 1-(3-azido-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine 
• 1463-10-1 5-Methyluridine 
• 114551-08-5 5'-O-(4,4'-dimethoxytrityl)-1-(2,3-anhydro-β-D-lyxofuranosyl)thymine 
• 138239-62-0 1-((2R,3R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 607351-45-1 1-(3-azido-3-deoxy-5-O-trityl-β-D-ribofuranosyl)thymine 
• 607351-46-2 O-2,2'-anhydro-1-(3-azido-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine 
• 120042-40-2 4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 215176-58-2 1-(3'-azido-3'-deoxy-β-D-ribofuranosyl)thymine 
• 65-71-4 thymin 
• 75096-64-9 3-Azido-3-deoxy-1,2-di-O-acetyl-5-O-(4-methylbenzoyl)-β-D-ribofuranose 
• 114551-13-2 1-{(2R,3S,4S,5S)-4-Azido-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Mycobacterium tuberculosis thymidine monophosphate kinase inhibitors: Biological evaluation and conformational analysis of 2′- and 3′-modified thymidine analogues

Mycobacterium tuberculosis thymidine monophosphate kinase (TMPKmt) has recently been introduced as a potential target for the structure-based design of anti-tuberculosis drugs. Based on the TMPKmt X-ray structure and previous S.A.R. studies, we synthesised the nucleoside analogues 3a-b, 6a-b, 7a-b, and 8a-b, modified in 2′- and 3′-position of the ribofuranose ring moiety. To our surprise, these analogues showed only moderate binding affinity (i.e. Ki between 118 and 1260 μM). This prompted us to investigate the conformational features of these nucleosides. We concluded that compounds of this series, especially 8a-b, are strongly biased towards the "Northern" furanose ring conformation, whereas X-ray crystallography reveals a preference of TMPKmt for the opposite "Southern" conformers. This paper covers the synthesis, biological evaluation and conformational features (i.e. preferred ring puckering) of the 2′- and 3′-modified dT analogues. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

1-(2,3-anhydro-β-D-lyxofuranosyl)cytosine derivatives as potential inhibitors of the human immunodeficiency virus

We report here that 1-(2,3-anhydro-β-D-lyxofuranosyl)cytosine has activity against the human immunodeficiency virus in vitro. A number of 2',3'-anhydro-β-D-lyxofuranosyl nucleoside derivatives were prepared, but none had the activity of the title compound. New efficient procedures were developed for the synthesis of 3'-deoxy-3'-alkyl- and 3'-deoxy-β-D-arabinosylpyrimidine derivatives.