Synthesis of new nucleoside analogues comprising a methylenecyclobutane unit

Danappe, Sophie; Pal, Ashutosh; Alexandre, Christian; Aubertin, Anne-Marie; Bourgougnon, Nathalie; Huet, François

doi:10.1016/j.tet.2005.04.023

Cited by 17 publications

(14 citation statements)

References 21 publications

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“…1′-Homocarbonucleosides with a cyclobutene ring had no significant activity against HIV-1 and HSV-1 [17]. In the series of 2′- or 3′-hydroxymetyl cyclopentane -1′-homocarbanucleosides, a few compounds presented a slight antiviral or anticancer activity [18,19], while 1′,3′-disubstituted cyclopentene analogs [20] or 2′,3′- cis diols [21], were found to be inactive.…”

Section: Introductionmentioning

confidence: 99%

New HSV-1 Anti-Viral 1′-Homocarbocyclic Nucleoside Analogs with an Optically Active Substituted Bicyclo[2.2.1]Heptane Fragment as a Glycoside Moiety

Tănase

Drăghici²,

Hanganu³

et al. 2019

Molecules

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New 1′-homocarbanucleoside analogs with an optically active substituted bicyclo[2.2.1]heptane skeleton as sugar moiety were synthesized. The pyrimidine analogs with uracil, 5-fluorouracil, thymine and cytosine and key intermediate with 6-chloropurine (5) as nucleobases were synthesized by a selective Mitsunobu reaction on the primary hydroxymethyl group in the presence of 5-endo-hydroxyl group. Adenine and 6-substituted adenine homonucleosides were obtained by the substitution of the 6-chlorine atom of the key intermediate 5 with ammonia and selected amines, and 6-methoxy- and 6-ethoxy substituted purine homonucleosides by reaction with the corresponding alkoxides. No derivatives appeared active against entero, yellow fever, chikungunya, and adeno type 1viruses. Two compounds (6j and 6d) had lower IC50 (15 ± 2 and 21 ± 4 µM) and compound 6f had an identical value of IC50 (28 ± 4 µM) to that of acyclovir, suggesting that the bicyclo[2.2.1]heptane skeleton could be further studied to find a candidate for sugar moiety of the nucleosides.

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Section: Introductionmentioning

confidence: 99%

New HSV-1 Anti-Viral 1′-Homocarbocyclic Nucleoside Analogs with an Optically Active Substituted Bicyclo[2.2.1]Heptane Fragment as a Glycoside Moiety

Tănase

Drăghici²,

Hanganu³

et al. 2019

Molecules

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“…In course of our research program toward nucleoside analogs, we have already prepared cyclobutene analogs of carbovir 1 , compounds 2 with a methylene spacer between the carbocycle and the heterocycle, nucleosides analogs with a methylene unit 3 and 4 , and mono‐ and polyhydroxylated analogs 6 and 7 (Figure ). We then planned to prepare trihydroxylated nucleoside analogs bearing a 1,2,3‐triazole moiety I and II via click azide‐alkyne cycloaddition following by cis ‐dihydroxylation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Triazolo Cyclobutane Nucleoside Analogs

Tran

Ngo

Dinh

et al. 2015

Bulletin Korean Chem Soc

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“…Some notable applications include ring cleavage and methylation to furnish an ester-aldehyde, 3 one-pot Wittig reaction-acetalization leading to an oxabicyclo[3.2.0]heptane, 4 preparation of methylenecyclobutane nucleoside analogues 5 and stereoselective organocatalyzed aldol condensation reactions in the presence of Lamino acids. 6 Recently, we discovered that 2-hydroxycyclobutanone 1 was a choice substrate for organocatalyzed condensation reactions with amines, providing access to optically active 2aminocyclobutanones.…”

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confidence: 99%