Isoxazolidinyl Nucleosides

Chiacchio, Ugo; Corsaro, Antonino; Giofrè, Salvatore V.; Romeo, Giovanni

doi:10.1002/9781118498088.ch17

Cited by 4 publications

(5 citation statements)

References 55 publications

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“…The reaction pathway involving lower value of ∆S will be the favored one. The ∆S(3,5) is smaller than ∆S (4,5). This suggests that 3,5-substituted isoxazolidine will be generated from the present cycloaddition reaction, in complete agreement with the experimental findings.…”

Section: -37supporting

confidence: 80%

“…The first option involved changes in the (2-deoxy)-D-ribofuranose moiety as the inversion of hydroxyl group configuration, their elimination leading to dideoxy-or dideoxy-dydehydro-nucleosides, their substitution/functionalization by various groups or cleavage of the sugar ring leading to acyclic nucleosides. 4 Other deeper structural modifications include the replacement of the oxygen atom by a methylene group, a sulfur or a nitrogen atom, or the additional insertion of a second heteroatom in the sugar moiety. [5][6] In particular, N,O-nucleosides, characterized by the presence of an isoxazolidine system as mimetic of the ribose spacer, have been designed and shown to be endowed with antiviral and/or antitumoral activity.…”

Section: Introductionmentioning

confidence: 99%

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5-(3-Phosphonated 1H-1,2,3-triazol-4-yl)isoxazolidines: synthesis, DFT studies and biological properties

Giofrè¹,

Romeo²,

Garozzo³

et al. 2015

Arkivoc

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5-Triazolyl-2-methylisoxazolidin-3-yl 3-phosphonates have been synthesized by 1,3-dipolar cycloaddition of N-methyl-C-diethoxyphosphorylnitrone and vinyl triazoles. The process showed a complete regioselectivity and a nearly exclusive cis stereoselectivity. M062X/6-31G(d,p) calculations rationalize the regio-and the stereochemical results. The formation of a hydrogen bond along a particular reaction channel significantly stabilizes both transition states and products related to cis-adducts. Biological tests indicate that the obtained compounds do not show relevant antiviral and anticancer activity.

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Section: -37supporting

confidence: 80%

Section: Introductionmentioning

confidence: 99%

5-(3-Phosphonated 1H-1,2,3-triazol-4-yl)isoxazolidines: synthesis, DFT studies and biological properties

Giofrè¹,

Romeo²,

Garozzo³

et al. 2015

Arkivoc

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“…Some of the tested compounds have proven to be potential antiproliferative drugs at a relatively low concentration . Some of these nucleoside analogues were also tested for their apoptotic pathway activation and were found to activate the caspase cleavage, inducing DNA fragmentation …”

Section: Introductionmentioning

confidence: 99%

Ene Reaction of Nitrosocarbonyl Mesitylene with the Cinnamyl Alcohol: Metabolic Activity and Apoptosis of the Synthetized 6-Chloropurine N,O-Nucleoside Analogues

et al. 2018

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Nitrosocarbonyl mesitylene intermediate undergoes an ene reaction with cinnamyl alcohol affording the corresponding 5-hydroxy-isoxazolidine in fair yields. The synthesized 5-acetoxy-isoxazolidine serves as synthon for the preparation of 6-chloropurine N,O-nucleoside analogues, according to the Vorbrüggen reaction. The compounds were evaluated for their metabolic and apoptotic activity, and their structure–activity relationship is discussed.

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“…After incorporation, these nucleoside analogues inhibit the elongation of viral DNA chain, preventing the incorporation of next incoming nucleotide, resulting in termination of the growing viral DNA chain [30]. In the last year, to search new biologically active nucleoside analogues, structural modifications on the sugar moiety and/ or the heterocyclic base of natural nucleosides have been performed in order to overcome the drawbacks mainly due to enzymatic degradation and/or to reduce the toxicity and the cross-resistance problems [31][32][33][34][35][36][37][38][39][40]. Currently, there are eight FDA-approved NRTIs: abacavir (ABC), didanosine (ddI), emtricitabine (FTC), lamivudine (3TC), stavudine (d4T), zalcitabine (ddC), zidovudine (AZT), and tenofovir disoprovil fumarate (TDF), a nucleotide RT inhibitor (Figure1).…”

Section: Introductionmentioning

confidence: 99%

Nanotechnology Approaches for Antiretroviral Drugs Delivery

Iannazzo¹,

Pistone²,

Romeo³

et al. 2015

Journal of AIDS and HIV infections

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The development of effective drug delivery approaches for the treatment of AIDS and HIV infection is a global challenge. The advent of multidrug, highly active antiretroviral therapy (HAART), have increased the life span of HIV-infected patients. However, it has not eradicated HIV infections, particularly in anatomically privileged sites, such as the brain, testes, gut, liver, kidney, and secondary lymphoid tissue. Several nanocarriers have been investigated in order to enhance the effective delivery of antiretroviral drugs for HIV prevention and therapy. This review focuses on the most recent and significant examples of nanotechnology-based approaches for the delivery of antiretroviral agents belonging to the classes of nucleoside-analog reverse transcriptase inhibitors (NRTIs) and nonnucleoside reverse transcriptase inhibitors (NNRTIs). Nanocarriers such as natural and synthetic polymeric nanoparticles, dendrimers, liposomes, and various drug conjugates have been discussed. These nanotechnology carriers are able to deliver the antiretroviral agents in a controlled and/or targeted manner thereby increasing the drug bioavailability and residence time at target sites with a considerable improvement in quality of HIV patients.

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Isoxazolidinyl Nucleosides

Cited by 4 publications

References 55 publications

5-(3-Phosphonated 1H-1,2,3-triazol-4-yl)isoxazolidines: synthesis, DFT studies and biological properties

5-(3-Phosphonated 1H-1,2,3-triazol-4-yl)isoxazolidines: synthesis, DFT studies and biological properties

Ene Reaction of Nitrosocarbonyl Mesitylene with the Cinnamyl Alcohol: Metabolic Activity and Apoptosis of the Synthetized 6-Chloropurine N,O-Nucleoside Analogues

Nanotechnology Approaches for Antiretroviral Drugs Delivery

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