Synthesis and Antiviral Activity of Carbocyclic Nucleosides Incorporating a Modified Cyclopentane Ring. Part 3: Adenosine and Uridine Analogues

Nieto, Marı́a Luisa; Blanco, J. M.; Caamaño, Olga; Fernández, Fernando Nieto; Garcı́a-Mera, Xerardo; López, Carmen; Balzarini, Jan; Clercq, Erik De

doi:10.1080/07328319908044879

Cited by 7 publications

(3 citation statements)

References 12 publications

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“…Nucleosides of this type are recognized by many receptors and enzymes due to their structural similarity to the natural nucleosides, however they display increased stability towards phosphorylase- and hydrolase-induced cleavage of the pseudo-glycosidic bond. Moreover, they possess a wide spectrum of biological activity, particularly, antiviral and anticancer properties [19,23,24,25,26,27,28,29,30,31,32,33]. Unfortunately, in some cases they have exhibited significant toxicity as a result of their conversion to triphosphate forms, which closely resemble natural nucleoside triphosphates (NTP), thus resulting in unwanted recognition by ATP metabolizing enzymes [34,35,36].…”

Section: Resultsmentioning

confidence: 99%

Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents

et al. 2018

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A series of novel 5′-norcarbocyclic derivatives of 5-alkoxymethyl or 5-alkyltriazolyl-methyl uracil were synthesized and the activity of the compounds evaluated against both Gram-positive and Gram-negative bacteria. The growth of Mycobacterium smegmatis was completely inhibited by the most active compounds at a MIC99 of 67 μg/mL (mc2155) and a MIC99 of 6.7–67 μg/mL (VKPM Ac 1339). Several compounds also showed the ability to inhibit the growth of attenuated strains of Mycobacterium tuberculosis ATCC 25177 (MIC99 28–61 μg/mL) and Mycobacterium bovis ATCC 35737 (MIC99 50–60 μg/mL), as well as two virulent strains of M. tuberculosis; a laboratory strain H37Rv (MIC99 20–50 μg/mL) and a clinical strain with multiple drug resistance MS-115 (MIC99 20–50 μg/mL). Transmission electron microscopy (TEM) evaluation of M. tuberculosis H37Rv bacterial cells treated with one of the compounds demonstrated destruction of the bacterial cell wall, suggesting that the mechanism of action for these compounds may be related to their interactions with bacteria cell walls.

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Section: Resultsmentioning

confidence: 99%

Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents

et al. 2018

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“…The observation that 4‘-substituted nucleosides also had wide-ranging biological activity spurred similar interest in their synthesis OH, alkyl, and aryl 8 substituents at the 4‘-position have been reported.…”

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confidence: 82%

Synthesis of 4‘-Methyl and 4‘-Cyano Carbocyclic 2‘,3‘-Didehydro Nucleoside Analogues via 1,4-Addition to Substituted Cyclopentenones

Hegedus

Cross

2004

J. Org. Chem.

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Carbocyclic 4'-methyl and 4'-cyano nucleoside analogues were synthesized using the Michael reaction to introduce the 4'-substituent and Pd-catalyzed allylic substitution to introduce the nucleoside base. Use of both the desired beta- and undesired alpha-1'-carbonate diastereomers in the Pd-catalyzed substitution was demonstrated in principle by epimerization of the alpha-diastereomer and kinetic diastereodifferentiation of a 1:1 alpha/beta mixture of 1'-carbonates.

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“…In recent years our research group has developed a number of derivatives of the antiviral CANs carbovir 2 and abacavir 3 by modifying their cyclopentene ring. 4 We have now replaced this ring with an indane system with a view to increasing liposolubility and thereby facilitating access to the central nervous system, an important reservoir for viral replication of HIV. 5 We report here the synthesis of (±)-cis-1-(3-hydroxymethyl-1-indanyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione (1) from the aminoalcohol (±)-cis-3-amino-1-indanylmethanol (4).…”

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confidence: 99%

A Short, Efficient Synthesis of Substituted Uracil: An Indane Carbocyclic Nucleoside

Fernández¹,

Garcı́a-Mera²,

Morales³

et al. 2001

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±)-cis-1-(3-Hydroxymethyl-1-indanyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione (1) was synthesised in two steps and with an overall yield of 51% from (±)-cis-3-amino-1-indanylmethanol (4) and 3-ethoxy-2-propenoyl isocyanate (3). The isocyanate 3 was prepared in 76% overall yield by reacting silver cyanate with 3-ethoxy-2-propenoyl chloride (2), which was obtained in one pot from ethyl vinyl ether and oxalyl chloride. The aminoalcohol (4) was prepared from phenylsuccinic anhydride in four steps.

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Synthesis and Antiviral Activity of Carbocyclic Nucleosides Incorporating a Modified Cyclopentane Ring. Part 3: Adenosine and Uridine Analogues

Cited by 7 publications

References 12 publications

Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents

Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents

Synthesis of 4‘-Methyl and 4‘-Cyano Carbocyclic 2‘,3‘-Didehydro Nucleoside Analogues via 1,4-Addition to Substituted Cyclopentenones

A Short, Efficient Synthesis of Substituted Uracil: An Indane Carbocyclic Nucleoside

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