Nucleosides, XXIII<sup>1</sup>. A Simple Access to 3′-Aminoxylo- and 3′,4′-Unsaturated Purine Nucleosides

Lichtenthaler, Frieder W.; Kitahara, Katsuhiko; Strobel, Kurt

doi:10.1055/s-1974-23449

Cited by 14 publications

(4 citation statements)

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“…9-(3-Benzamido-3-deoxy- β - d -xylofuranosyl)adenine (2a). To a cooled (0 °C) suspension of 420 mg (1.58 mmol) of amine 1 , in 30 mL of dry CH 2 Cl 2 −pyridine (3:1) was added 433 mg (1.91 mmol) of benzoic anhydride. After the mixture was stirred for 3 h at room temperature, the reaction was quenched with 5 mL of H 2 O.…”

Section: Methodsmentioning

confidence: 99%

N⁶-Cyclopentyl-3‘-substituted-xylofuranosyladenosines: A New Class of Non-Xanthine Adenosine A₁ Receptor Antagonists

et al. 1997

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The present study explores the C-3' site of the 3-deoxy-3-xylofuranosyl ring of nucleoside analogues with an adenine or N6-cyclopentyladenine (CPA) base moiety and evaluates the effect on adenosine receptor affinity. Two series of sugar-modified adenosines, i.e., 3'-amido-3'-deoxyadenosines and 3'-amidated 3'-deoxyxylofuranosyladenines, were synthesized and tested for their affinity at A1 and A2a receptors in rat brain cortex and rat striatum, respectively. The modest affinity found in the "xylo series" prompted us to synthesize the corresponding N6-cyclopentyl derivatives, which proved to be well accommodated by the A1 receptors with potencies in the lower nanomolar range. This represents a new perspective in the purinergic field. The absence of a GTP-induced shift, i.e., the ratio between the affinities measured in the presence and absence of 1 mM GTP indicates an antagonistic behavior of this new class of CPA analogues.

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Section: Methodsmentioning

confidence: 99%

N⁶-Cyclopentyl-3‘-substituted-xylofuranosyladenosines: A New Class of Non-Xanthine Adenosine A₁ Receptor Antagonists

et al. 1997

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“…The synthesis of HLB-0532247 ( 1 ) was completed using established methods for the preparation of nucleosides containing dehydrated ribose rings. − The synthesis of 1 commences with a two-step protection sequence to yield bis-protected cytidine 3 , , which can undergo an oxidative esterification, affording 4 in 78% yield (Scheme ). , Base-mediated tandem elimination and deprotection of 4 followed by reprotection of the 2′-alcohol with TBSCl gives 5 in 77% yield in a one-pot procedure. , Reduction of the carboxylic ester to the primary alcohol yields 7 .…”

Section: Resultsmentioning

confidence: 99%

A Chemical Strategy for Intracellular Arming of an Endogenous Broad-Spectrum Antiviral Nucleotide

et al. 2021

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The naturally occurring nucleotide 3′-deoxy-3′,4′-didehydro-cytidine-5′-triphosphate (ddhCTP) was recently found to exert potent and broad-spectrum antiviral activity. However, nucleoside 5′-triphosphates in general are not cell-permeable, which precludes the direct use of ddhCTP as a therapeutic. To harness the therapeutic potential of this endogenous antiviral nucleotide, we synthesized phosphoramidate prodrug HLB-0532247 (1) and found it to result in dramatically elevated levels of ddhCTP in cells. We compared 1 and 3′-deoxy-3′,4′-didehydro-cytidine (ddhC) and found that 1 more effectively reduces titers of Zika and West Nile viruses in cell culture with minimal nonspecific toxicity to host cells. We conclude that 1 is a promising antiviral agent based on a novel strategy of facilitating elevated levels of the endogenous ddhCTP antiviral nucleotide.

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“…Bt was found to be more experimentally convenient and economical to use the iodo product 2, obtained by treatment of tubercidin (I) with a-acetoxyisobutyryi chloride and excess sodium iodide (5b). This is in contrast with reactions involving ader~osine in which the orthoester] pivalyl chloride route proceeds sn-~oothly (5d) and avoids problems of incomplete reaction, multiple acylation, and significant glycosyl bond cleavage noted with the Mattocks-Moffatt procedure (6,7). 6 2 situ generation of cx-acetoxyisobutyryl iodide in acetonitrile provided smooth reaction with I at room temperature to give 4-amino-7- (2) in quantitative yieid (56) (see Scheme 1).…”

Section: -8-pivalyl-p-d-xylofuranosyl)pyrrolo[23 -D L -mentioning

confidence: 99%

“…Le dtrive 0-isopropylidtne-3',5' (6a) de 5 est mesylt et donne 6b qui est dkprotege en milieu acide. Le trans hydroxy mesylate rksultant, par traitement basique, donne l'amino-4 (anhydro-2,3 a-D-lyxofuranosy1)-7 pyrrolo[2,3-dlpyrimidine (7). Cet tpoxyde lyxo fournit l'amino-4 P-Darabinofuranosyl-7 pyrrolo[2,3-dlpyrimidine (8) sous l'action du benzoate de sodium dans la DMF.…”

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Nucleic acid related compounds. 25. Syntheses of arabino, xylo, and lyxo-anhydro sugar nucleosides from tubercidin ribo-epoxide

Robins¹,

Fouron²,

Muhs³

1977

Can. J. Chem.

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. Can J. Chem. 55, 1260Chem. 55, (1977. Treatment of the trans iodohydrin acetate, 4-arnino-7-(3-iodo-3-deoxy-2-O-acetyl-5-0-[2,5,5-trimethyl-1,3-dioxolan-4-on-2-yl]-~-~-xylofuranosyl)pyrrolo[2,3-d]pyrimidine (2) with methanolic ammonia gave 2',3'-anhydrotubercidin (3) in 96% yield. N4,N4,05'-Tribenzoylation of 3 gave 4, which is stabilized against intramolecular cyclization. Treatment of 4 with boron trifluoride etherate (3',5'-benzoxonium ion formation) followed by deblocking gave 4-amino-7-B-D-xylofuranosylpyrrolo[2,3-dlpyrimidine (5) in 91% overall yield from tubercidin (1). The 3',5'-0-isopropylidene derivative (6a) of 5 was mesylated to give 6b which was deprotected in acid and the resulting trans hydroxy mesylate was treated with base to give 4-amino-7-(2,3-anhydro-P-D-lyxofuranosyl)pyrrolo[2,3-d]rmdne (7

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Nucleosides, XXIII¹. A Simple Access to 3′-Aminoxylo- and 3′,4′-Unsaturated Purine Nucleosides

Cited by 14 publications

References 0 publications

N⁶-Cyclopentyl-3‘-substituted-xylofuranosyladenosines: A New Class of Non-Xanthine Adenosine A₁ Receptor Antagonists

N⁶-Cyclopentyl-3‘-substituted-xylofuranosyladenosines: A New Class of Non-Xanthine Adenosine A₁ Receptor Antagonists

A Chemical Strategy for Intracellular Arming of an Endogenous Broad-Spectrum Antiviral Nucleotide

Nucleic acid related compounds. 25. Syntheses of arabino, xylo, and lyxo-anhydro sugar nucleosides from tubercidin ribo-epoxide

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Nucleosides, XXIII1. A Simple Access to 3′-Aminoxylo- and 3′,4′-Unsaturated Purine Nucleosides

Cited by 14 publications

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N6-Cyclopentyl-3‘-substituted-xylofuranosyladenosines: A New Class of Non-Xanthine Adenosine A1 Receptor Antagonists

N6-Cyclopentyl-3‘-substituted-xylofuranosyladenosines: A New Class of Non-Xanthine Adenosine A1 Receptor Antagonists

A Chemical Strategy for Intracellular Arming of an Endogenous Broad-Spectrum Antiviral Nucleotide

Nucleic acid related compounds. 25. Syntheses of arabino, xylo, and lyxo-anhydro sugar nucleosides from tubercidin ribo-epoxide

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Nucleosides, XXIII¹. A Simple Access to 3′-Aminoxylo- and 3′,4′-Unsaturated Purine Nucleosides

N⁶-Cyclopentyl-3‘-substituted-xylofuranosyladenosines: A New Class of Non-Xanthine Adenosine A₁ Receptor Antagonists

N⁶-Cyclopentyl-3‘-substituted-xylofuranosyladenosines: A New Class of Non-Xanthine Adenosine A₁ Receptor Antagonists