Nucleosides and nucleotides. 159. Synthesis of thietane nucleosides via the Pummerer reaction as a key step

Nishizono, Naozumi; Koike, Nobuaki; Yamagata, Yuriko; Fujii, Satoshi; Matsuda, Akira

doi:10.1016/0040-4039(96)01719-4

Cited by 50 publications

(18 citation statements)

References 14 publications

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“…Matsuda et al reported the first synthesis of thietanosyl nucleosides of Type V and W [33]. The optically active sulfoxide 97 was obtained from L-ascorbic acid 88.…”

Section: '-Aza-nucleosidesmentioning

confidence: 99%

Sugar-Modified Nucleosides in Past 10 Years, A Review

Ichikawa¹,

Kato

2001

CMC

179

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In the search for effective, selective, and nontoxic antiviral and antitumour agents, a variety of strategies have been devised to design nucleoside analogs. These strategies have involved several formal modifications of the naturally occurring nucleosides, especially, alteration of the carbohydrate moiety. Since the naturally occurring purine nucleoside analog oxetanocin A and its derivatives have been found to be effective as anti-HIV-1 and anti-herpes virus agents in 1986, the syntheses of different types of sugar-modified nucleoside analogs have been reported. In this review we will give an overview of the sugar-modified nucleosides synthesized since the late 1990 according to their structural types along with the synthetic routes of some selected nucleosides.

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“…Matsuda et al reported the first synthesis of thietanosyl nucleosides of Type V and W [33]. The optically active sulfoxide 97 was obtained from L-ascorbic acid 88.…”

Section: '-Aza-nucleosidesmentioning

confidence: 99%

Sugar-Modified Nucleosides in Past 10 Years, A Review

Ichikawa¹,

Kato

2001

CMC

179

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“…The pellet was solubilized with vortexing in 100 μl virus solubilization buffer (VSB) containing 0.5% Triton X-100, 0.8 M NaCl, 0.5 mM phenylmethylsulfonyl fluoride, 20% glycerol, and 0.05 M Tris, pH 7.8. Ten μl of each sample were added to 75 μl RT reaction mixture (0.06 M Tris, pH 7.8, 0.012 M MgCl 2 , 0.006 M dithiothreitol, 0.006 mg/ml poly (rA) n oligo (dT) [12][13][14][15][16][17][18] , 96 μg/ml dATP, and 1 μM of 0.08 mCi/ml 3 H-thymidine triphosphate (Moravek Biochemicals, Brea, CA)) and incubated at 37°C for 2 h. The reaction was stopped by the addition of 100 μl 10% trichloroacetic acid containing 0.05% sodium pyrophosphate. The acid insoluble product was harvested onto filter paper using a Packard Harvester (Meriden, CT), and the RT activity was read on a Packard Direct Beta Counter (Meriden, CT).…”

Section: Antiviral Assaymentioning

confidence: 99%

Synthesis and Anti-HIV Activity of d- and l-Thietanose Nucleosides

et al. 2006

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Various D-and L-thietanose nucleosides (22-27, 33-35, 50-52, 58-60) were synthesized from D-and L-xylose. The four-membered thietane ring was efficiently synthesized by the cyclization of 1-thioacetyl-3-mesylate (4/38) under basic conditions. Condensation with various heterocyclic bases was conducted via Pummerer-type rearrangement to afford various nucleoside derivatives. Among the synthesized nucleosides, D-uridine (23), D-cytidine (24), D-5-fluorocytidine (25) and L-cytidine (52) analogs showed moderate anti-HIV activity with EC 50 of 6.9, 1.3, 5.8 and 14.1 μM, respectively. However, these four nucleoside analogs are cytotoxic in PBM and CEM cells. The other nucleosides are neither active nor cytotoxic. Interestingly, the oxetanocin A analog 33 was not active. Comparison of the minimized RTs complexed with the corresponding triphosphates of the cytidine analog 24 and the adenosine analog 33 by molecular modeling studies showed that there is no difference in the binding mode of the triphosphate of the cytidine analog 24 to the active site of HIV-1 RT from that of the triphosphate of the adenosine analog 33. Modeling studies on the initial monophosphorylation step by deoxycytidine kinase showed that the catalytic efficiency of phosphorylation through a nucleophilic attack of the 4′-hydroxyl group of thietanose on the γ-phosphate of ATP is diminished in the case of L-cytidine analog (52) due to the increased distance between the 4′-hydroxyl group and the γ-phosphate.

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“…A new thymidine thietane nucleoside 347 was synthesized via the Pummerer rearrangement of the corresponding 345 in the presence of thymine, TMSOTf, Et 3 N, and ZnI 2 as a key step [51]. Compound 341, derived from D-isoascorbic acid 340 [52], was deacetalized followed by tritylation to 342, which was reduced and then mesitylated to afford 343.…”

Section: Synthesis Of Miscellaneous Thionucleosidesmentioning

confidence: 99%

The Properties of 4′‐Thionucleosides

Yokoyama

2008

Modified Nucleosides

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Nucleosides and nucleotides. 159. Synthesis of thietane nucleosides via the Pummerer reaction as a key step

Cited by 50 publications

References 14 publications

Sugar-Modified Nucleosides in Past 10 Years, A Review

Sugar-Modified Nucleosides in Past 10 Years, A Review

Synthesis and Anti-HIV Activity of d- and l-Thietanose Nucleosides

The Properties of 4′‐Thionucleosides

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