Non-catalytic Fusion Reaction of 1, 2, 3, 5-Tetra-<i>O</i>-acetyl-β-<scp>d</scp>-ribofuranose with Purine Derivatives

Ishido, Yoshiharu; Matsuba, Teruo; Hosono, A.; Fujii, Keisuke; Sato, Tetsuo; Isome, Sadanori; Maruyama, Akira; Kikuchi, Yasuhiko

doi:10.1246/bcsj.40.1007

Cited by 16 publications

(5 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The yield of IX was thus increased 2~ 3 times more than that by the earier procedure. 3) Although the yield of IX was lower than that (65 %) by the mercury method,') the procedure is appreciable in respects of simplicity of the manipulation of the reaction and no mercury contamination.…”

Section: Please Scroll Down For Articlementioning

confidence: 92%

“…The yield of 6-chloro-9-tl-D-ribofuranosylpyrine, which is an important intermediate for the synthesis of ribosylzeatin and N8-isopentenyladenosine, was significantly increased compared with that reported by earlier workers. 3 ) This paper deals with an improved ribosylation of 6-chloropurine and its 2-methyIthio derivative by the fusion procedure using iodine.…”

Section: Please Scroll Down For Articlementioning

confidence: 99%

See 1 more Smart Citation

Ribosylation of 6-Chloropurine and Its 2-Methylthio Derivative by a Fusion Procedure Using Iodin

Sugiyama

Hashizume

1978

Agricultural and Biological Chemistry

View full text Add to dashboard Cite

Section: Please Scroll Down For Articlementioning

confidence: 92%

Section: Please Scroll Down For Articlementioning

confidence: 99%

Ribosylation of 6-Chloropurine and Its 2-Methylthio Derivative by a Fusion Procedure Using Iodin

Sugiyama

Hashizume

1978

Agricultural and Biological Chemistry

View full text Add to dashboard Cite

“…1-0 -D-Ribofuranosyl-1,2,4-triazole-3-carboxamidrazone (9). A solution of 4 (1.76 g, 5.0 mmol) in EtOH (50 ml) was treated with NjH4 (97%, 1.0 ml) and the solution was stirred at room temperature for 48 hr.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and antiviral activity of 1,2,4-triazole-3-thiocarboxamide and 1,2,4-triazole-3-carboxamidine ribonucleosides

Witkowski¹,

Robins²,

Khare³

et al. 1973

J. Med. Chem.

View full text Add to dashboard Cite

The syntheses of ribonucleosides structurally related to 1-ß-D-ribofuranosyl-1,2,4-triazole-3-carboxamide (1) are described and their antiviral activity is compared with that of 1. Both the acid-catalyzed fusion procedure and glycosylation of the appropriate trimethylsilyl derivative provided 3-cyano-l-(2,3,5-tri-0-acetyl-|3-D-ribofuranosyl)-l,2,4-triazole (4) in 80% yield. ß-D-Ribofuranosyl-l,2,4-triazole-3-thiocarboxamide (2) and 1-ß-D-ribofuranosyl-1,2,4-triazole-3-carboxamidine hydrochloride (3) and related nucleosides were prepared from 4. In tissue culture, 3 exhibited activity against herpes simplex, rhino, and parainfluenza viruses, similar to that shown by 1, while 2 was effective only against herpes simplex virus. Against lethal influenza A2 virus infections in mice, 3 was effective at 75 mg/kg/day compared with 1 which showed significant activity at 37.5 mg/kg/day.The synthetic nucleoside 1 -ß-D -ribofuranosyl-1,2,4-triazole-3-carboxamide 1,2 (virazole) (1) has been shown by our laboratory to exhibit a broad spectrum of activity against both DNA and RNA viruses in vitro and in vivo.2 Our interest in nucleosides structurally related to 1 has prompted us to investigate3'4 the synthesis and antiviral activity of 1ß-D-ribofuranosyl-l,2,4-triazole-3-thiocarboxamide (2) and 1-ß-D-ribofuranosyl-1,2,4-triazole-3-carboxamidine (3). These nucleosides, while retaining steric requirements very similar to those of the corresponding carboxamide nucleoside 1, differ in hydrogen bonding properties (S and N vs. 0) of the 3 substituent on the triazole.As a route to both the thiocarboxamide (2) and carboxamidine (3) triazole nucleosides, the synthesis of 3-cyano-l-(br s, 2, NH,); Xmax ( , ) 230 nm (e 6000), 287 (6800). Anal.

show abstract

“…(629) Using this procedure, 8-bromo-2'-O-p-toluenesulfonylguanosine (585) was prepared from the stannylene derivative (586) and then converted to 8,2'-anhydro-9-tJ-o-arabinofuranosyl-8-oxyguanine (587) by treatment of (585) with acetic anhydride/acetic acid, followed by ammonia. (630) 9-tJ-D-Arabinofuranosyl-8-chloroadenine undergoes a silica-gel-catalyzed cyclization to provide 8,2'-anhydro-p-D-arabinofuranosyl-8-oxyadcnine (582). (396) The synthetic utility of 8,2'-anhydro-8-oxypurine nucleosides has proved substantial.…”

mentioning

confidence: 99%

Synthesis and Properties of Purine Nucleosides and Nucleotides

Srivastava

Robins²,

Meyer

1988

Chemistry of Nucleosides and Nucleotides

View full text Add to dashboard Cite

Non-catalytic Fusion Reaction of 1, 2, 3, 5-Tetra-O-acetyl-β-d-ribofuranose with Purine Derivatives

Cited by 16 publications

References 8 publications

Ribosylation of 6-Chloropurine and Its 2-Methylthio Derivative by a Fusion Procedure Using Iodin

Ribosylation of 6-Chloropurine and Its 2-Methylthio Derivative by a Fusion Procedure Using Iodin

Synthesis and antiviral activity of 1,2,4-triazole-3-thiocarboxamide and 1,2,4-triazole-3-carboxamidine ribonucleosides

Synthesis and Properties of Purine Nucleosides and Nucleotides

Contact Info

Product

Resources

About