Synthesis and anti-HIV activity of 3′-deoxy-3′-(N-hydroxyamino) analogues of nucleosides

Tronchet, J. M. J.; Zsely, M.; Čapek, Karel; Naide, Fabienne de Villedon de

doi:10.1016/s0960-894x(00)80464-3

Cited by 12 publications

(3 citation statements)

References 9 publications

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“…It is formed by 20 compounds (3 active and 17 inactive) selected from recent literature and was never used in the training or crossvalidation process. 21,24,29,36,41,[46][47][48][49][50][51][52][55][56][57][58] The criterion of activity selected in this study is based on the effective concentration EC 50 on MT4 assay. As we are interested in selecting only very active compounds against the selection of moderate or poorly active ones, we have taken as cutoff value of activity an EC 50 of 10 µM.…”

Section: Methodsmentioning

confidence: 99%

“…Data Sets. A data set of 141 pyrimidyl nucleoside derivatives was collected from the literature for the present study. − This data set is divided into two subgroups. A set of 65 compounds (21 active and 44 inactive) was used as the training set for developing the classification model with TOPS-MODE.…”

Section: Methodsmentioning

confidence: 99%

“…Another data set of pyrimidyl nucleoside derivatives was used as an external prediction set. It is formed by 20 compounds (3 active and 17 inactive) selected from recent literature and was never used in the training or cross-validation process. ,,,,,− ,− …”

Section: Methodsmentioning

confidence: 99%

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In Silico Studies toward the Discovery of New Anti-HIV Nucleoside Compounds with the Use of TOPS-MODE and 2D/3D Connectivity Indices. 1. Pyrimidyl Derivatives

Estrada

Vilar

Uriarte

et al. 2002

J. Chem. Inf. Comput. Sci.

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Computational approaches are developed to design or rationally select, from structural databases, pyrimidyl nucleosides with anti-HIV activity. A data set of 141 nucleoside derivatives was selected from literature, and a discriminant function was derived with the use of TOPS-MODE descriptors. The model is able to classify correctly 83% of the compounds in a training set and 88.5% in a cross-validation set. The use of an external prediction set selected from the most recent literature proved that the model has good predictive ability, with a good classification of 85% of the compounds in this set. This model permitted the structural interpretation of the anti-HIV activity of these nucleoside analogues. This interpretation is formulated as several rules concerning the influence of several structural features on the activity/inactivity of such compounds. A QSAR model for the most active compounds was developed with the combined use of 2D and 3D connectivity indices. This model explains 88% of the variance in the activity of these compounds in MT4 assay. The combination of both models will permit the selection of pyrimidyl nucleoside leads and their optimization to improve the potency of the selected ones.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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In Silico Studies toward the Discovery of New Anti-HIV Nucleoside Compounds with the Use of TOPS-MODE and 2D/3D Connectivity Indices. 1. Pyrimidyl Derivatives

Estrada

Vilar

Uriarte

et al. 2002

J. Chem. Inf. Comput. Sci.

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Hydroxylamine, Oxime and Hydroxamic Acid Derivatives of Nucleic Acids

Kojima

Komatsu

2010

Patai's Chemistry of Functional Groups

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Hydroxylamines directly react with nucleobases in genomic DNA, and the damaged nucleobases induce genetic mutations by forming non‐canonical base pairs with natural bases. In contrast, some nucleoside analogues containing hydroxylamine and its related derivatives are known to possess antiviral and anticancer activities by mimicking natural nucleosides. In addition, oligonucleotides with phosphate backbones modified with hydroxylamines show nuclease resistance required for oligonucleotide therapeutics. This chapter provides the fundamental functions and the applications of hydroxylamine, oxime and hydroxamic acid groups on nucleic acids, consisting of four contents (1. Reactions of hydroxylamine and O ‐methylhydroxylamine with nucleobases, 2. Nucleoside and nucleotide analogues consisting of hydroxylamine, oxime and hydroxamic acid groups, 3. A series of oligonucleotides modified at backbone and sugar moieties with these functional groups, and 4. Application for the detection and quantification of DNA lesions by aminooxy probes). Novel nucleic acids will be developed by understanding potential functions of hydroxylamine and its related derivatives.

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Modified dideoxynucleosides: Synthesis of 2′-N-alkyl-3′-hydroxyalkyl-1′,2′-isoxazolidinyl thymidine and 5-fluorouridine derivatives

et al. 1996

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Synthesis and anti-HIV activity of 3′-deoxy-3′-(N-hydroxyamino) analogues of nucleosides

Cited by 12 publications

References 9 publications

In Silico Studies toward the Discovery of New Anti-HIV Nucleoside Compounds with the Use of TOPS-MODE and 2D/3D Connectivity Indices. 1. Pyrimidyl Derivatives

In Silico Studies toward the Discovery of New Anti-HIV Nucleoside Compounds with the Use of TOPS-MODE and 2D/3D Connectivity Indices. 1. Pyrimidyl Derivatives

Hydroxylamine, Oxime and Hydroxamic Acid Derivatives of Nucleic Acids

Modified dideoxynucleosides: Synthesis of 2′-N-alkyl-3′-hydroxyalkyl-1′,2′-isoxazolidinyl thymidine and 5-fluorouridine derivatives

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