A novel synthesis of “double headed” nucleosides “reversed” nucleosides

Kasnar, B.; Skaric, V.; Klaić, Branimir; Žinić, Mladen

doi:10.1016/s0040-4039(00)74067-6

Cited by 21 publications

(13 citation statements)

References 8 publications

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“…23,24 Following our previously described approach to reversed nucleosides, the sodium salts of the uracil derivatives 4−6 were reacted with ribofuranoside 3 giving the corresponding reversed nucleosides 7, 8 and 10 (Scheme 1). 19,21 It was reported that the condensation of thymine sodium salt with the tosyl monosaccharide 3 gave two regioisomers containing the ribofuranoside attached at N1′ or N3′ position of the thymine ring. H NMR spectra.…”

Section: Resultsmentioning

confidence: 99%

“…14−20 In our previous communication we have reported on the synthesis of several partially and fully deprotected reversed and double headed nucleosides the former incorporating uracil or 5-iodouracil attached by N1′ at the C5 position of ribofuranose. 19,21 In this work we present detailed experimental conditions for the synthesis of such reversed nucleosides and extend the synthesis to the highly interesting reversed nucleoside 13 incorporating 5-fluorouracil, the well-known anticancer drug. We also report on the preparation of the novel type of the nucleoside derivatives 9, 11 and 15 containing the ribose fragments attached at both, the N1′ and N3′ positions of 5′-iodo and 5′-fluorouracil bases.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides

et al. 2015

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Abstract. An efficient approach to reversed nucleosides which enables their synthesis in gram quantities is described. N-1′-Pyrimidine reversed nucleosides were prepared by treating of the sodium salt of pyrimidine bases with protected 5-tosyl ribose. Additionally, N-1′,N-3′-disubstituted reversed nucleosides were isolated in the condensation reactions with the 5-halogen pyrimidines. Using the Sonogashira coupling of 5′-iodouracil reversed nucleoside with ethynyltrimethyl silane gave 5′-ethynyl derivative which was further transformed into 5′-acetyl reversed nucleoside. Biological activity of deprotected reversed nucleosides was validated on the panel of six human carcinoma cell lines (HeLa, MIAPaCa2, Hep2, NCI-H358, CaCo-2, and HT-29). 5′-Iodouracil derivative displayed moderate growth inhibition activity against human colon carcinoma (CaCo-2) cells.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides

et al. 2015

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“…[24][25][26][27][28][29] Our group has a long-term experience in design, synthesis, and characterization of biologically active nucleoside derivatives. [30][31][32][33] Previously, we have synthesized N-sulfonylpyrimidine derivatives I (Figure 2) as a new type of sulfonylcycloureas. [34][35][36][37] These compounds showed strong antiproliferative activity on human tumor cell lines, in in vitro [38][39][40][41] and in vivo [42][43][44][45] conditions.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis and In vitro Cytostatic Activity of 5-Aminosulfonyl Uracil Derivatives

Ismaili

Ban

Matić

et al. 2019

Croat. chem. acta (Online)

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Efficient synthesis of 5-aminosulfonyl uracil derivatives 2-9 and results of their antiproliferative activity are provided. Sulfonylation of the amino group in 5-aminouracil 1 with selected arylsulfonyl chlorides occurs regioselectively when the reaction is carried out in pyridine at room temperature. Simple isolation of the products by recrystallization of the crude product mixture from aqueous methanol provides good to excellent yields. The prepared 5-aminosulfonyl uracil derivatives 2-9 were tested for the antiproliferative activity on a panel of seven tumor cell lines of different histological origin (HeLa, Caco-2, NCI-H358, Raji, HuT78, Jurkat, K562) and normal MDCK I cells. Derivatives 2-9 were found more efficient to lymphoma and leukemia cells compared to solid tumor and normal cells.

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“…[3][4][5][6][7][8][9][10] Indeed, the modern structural features of nucleosides are somewhat different from those present in poly-ribonucleotides RNA and DNA, [11] by means of variations in sugar, heterocyclic moieties and the various modes of attachments between the two major components (sugar and heterocycle). The literature of the new kinds of nucleosides is increasing and a lot of variations and kinds of nucleosides with dinuclear nucleosides [12,13] and others were also reported. [14,15] The wide occurrences of heterocyclic compounds in bioactive natural products and pharmaceuticals have made them as important synthetic targets.…”

Section: Introductionmentioning

confidence: 99%

Computational Study of some Double Headed Acyclo-C-Nucleosides

Amara

Tchouar

Belaidi

2015

ILCPA

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ABSTRACT. In the present paper we have a focus in a study of theoretical characterization of three double headed acyclo-C-nucleosides, which are a recent target of experimental studies. The structural and electronic properties of double headed acyclo-C-nucleosides, 1,4-bis(3-mercapto-1H-1,2,4-triazol-5-yl)butane-1,2,3,4-tetrol, 1,4-bis(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)butane-1,2,3,4-tetrol and 5,5'-(1,2,3,4-tetrahydroxybutane-1,4-diyl)bis(1,3,4-oxadiazole-2(3H)-thione), have been investigated theoretically by performing semi-empirical molecular orbital, ab initio Hartree-Fock (HF) and Density Functional Theory (DFT) calculations. Geometries of the three molecules are optimized at the level of Austin Model 1 (AM1). The electronic properties and relative energies of the molecules have been calculated by HF and DFT in the ground state.

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A novel synthesis of “double headed” nucleosides “reversed” nucleosides

Cited by 21 publications

References 8 publications

Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides

Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides

An Efficient Synthesis and In vitro Cytostatic Activity of 5-Aminosulfonyl Uracil Derivatives

Computational Study of some Double Headed Acyclo-C-Nucleosides

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