Synthesis of anti-HIV nucleoside conjugates with lipophilic diol compounds

Tuchnaya, O. A.; Елизарова, С Н; Шарикова, С. А.; Шастина, Н. С.; Stepanov, A. E.; Yurkevich, A. M.; Швец, В. И.

doi:10.1007/s11094-006-0108-5

Cited by 3 publications

(4 citation statements)

References 27 publications

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“…2,3,4,5-Tetra-O-benzyl-D,L-iditol, X was prepared as described previously [23], 2,3,4,5-tetra-O-benzyl-D,L-iditol 1,6-di-O-hydrogen phosphonate I was synthesized as described in [28], 1(3)-O-b-benzoylpropionyl-2,3 (I), 5,6(4)-di-O-isopropylidene-sn-myo-inositol II were synthesized as described previously [32], di(2-cyanoethyl)chlorophosphite was synthesized as described in [30].…”

Section: Methodsmentioning

confidence: 99%

“…Dimeric myo-inositol derivative VI was prepared: initially, di-H-phosphonate I, prepared using a published method [28], was dried by evaporation with pyridine and was condensed in the same solvent with the hydroxyl component, the pentasubstituted derivative of myo-inositol II, in the presence of condensing agent pivaloyl chloride (Piv-Cl) (Scheme 1). When TLC analysis showed complete conversion of I into the corresponding bisphosphonate diester (about 30 min), oxidization with iodine solution in aqueous pyridine was performed without extraction.…”

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confidence: 99%

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Synthesis of anionic derivatives of myo-inositol and other polyols and investigation of their antiviral activity

et al. 2008

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The search for new, effective antiviral agents currently includes assessment of polyanionic compounds of various structures; these are highly active inhibitors of viral penetration into cells. The present report describes the preparation of phosphate and sulfate derivatives based on 2,3,4,5-tetra-O-benzyl-D,L-iditol, 1,12-dodecanediol, and a dimeric analog of inositol-containing phospholipids. The dimeric derivative, which contains two myo-inositol cyclitol rings linked by a single hydrophobic fragment, was synthesized at high yield using the H-phosphonate method. The antiviral activity of the series of compounds synthesized here was assessed against a panel of viruses. All were inactive against rhinoviruses; the disulfate of tetra-O-benzyl-D, L-iditol inhibited Coxsackie virus and had the greatest cytotoxicity; the disulfate of 1,2-dodecanediol was inactive against all viruses, while the diphosphate of 2,3,4,5-tetra-O-benzyl-D,L-iditol and the monosulfate of 1,2-dodecanediol were active against herpes simplex viruses types 1 and 2. 4 0091-150X/08/4201-0004

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Section: Methodsmentioning

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Synthesis of anionic derivatives of myo-inositol and other polyols and investigation of their antiviral activity

et al. 2008

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“…The second pathway for synthesizing phospho-diester V employed the reaction of penta-substituted myo-inositol derivative I with di-H-phosphonate idite IV, which was obtained by the literature method [15], under analogous conditions with activation by pivaloylchloride. Isolation and purification by column chromatography isolated V in 74.5% yield.…”

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Synthesis of new derivatives of inositolcontaining phospholipid dimer analogs as potential inhibitors of virus adsorption

et al. 2011

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The majority of known agents against human immunodeficiency virus (HIV) are targeted at the virus enzymes protease and integrase but do not prevent HIV entry into host cells. Therefore, it is critical to seek small polyanionic molecules as potential inhibitors of virus adsorption. Inositol-containing phospholipids, which are naturally occurring biologically active compounds that are involved in cell regulation, may be promising lead compounds for antiviral drug design. In the present study, dimer analogs of inositol-containing phospholipids were synthesized using the H-phosphonate method. Carboxymethyl and sulfate derivatives based on them were obtained and proposed as potential virus adsorption inhibitors.

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“…Therefore, the hydrolysis kinetics of AZT-containing conjugates V, VII, and IXa in various buffers [12,17] that modeled the pH values of the GI tract, blood, lymphatic system, etc. were measured beforehand.…”

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Synthesis and properties of 3′-azido-3′-deoxythymidine derivatives of glycerolipids

et al. 2011

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A promising approach to enhancing the bioavailability of hydrophilic therapeutic agents including anti-HIV nucleosides is designing their pseudotriglyceride derivatives that may mimic natural lipids and take advantage of their metabolic pathways resulting in improved delivery to target cells. The synthesis of a series of new 1,3-diglycerides and AZT conjugates employing various linkage types between the pharmacophore residue and the spacer part of the hydrophobic moiety (ester or phosphodiester) is described. The hydrolytic properties of the synthesized liponucleosides (in buffer solutions and under the action of pancreatic lipase) have been studied. Liposomes based on these AZT-containing prodrugs have been obtained.

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Synthesis of anti-HIV nucleoside conjugates with lipophilic diol compounds

Cited by 3 publications

References 27 publications

Synthesis of anionic derivatives of myo-inositol and other polyols and investigation of their antiviral activity

Synthesis of anionic derivatives of myo-inositol and other polyols and investigation of their antiviral activity

Synthesis of new derivatives of inositolcontaining phospholipid dimer analogs as potential inhibitors of virus adsorption

Synthesis and properties of 3′-azido-3′-deoxythymidine derivatives of glycerolipids

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