Synthesis of New 1,2,3-Triazole Acyclonucleoside Analogues of ACV and HBG

Lazrek, H. B.; Taourirte, Moha; Oulih, T.; Lebtoumi, M.; Barascut, J. L.; Imbach, Jean‐Louis

doi:10.1080/07328319708006145

Cited by 20 publications

(10 citation statements)

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“…The applicability of a 1,2,3-triazole ring as a replacement of sugar [17][18][19] or nucleobase moieties 17,[19][20][21] as well as an additional linker between a phosphonoalkyl unit and a nucleobase has been widely explored [22][23][24][25][26][27][28] including our achievements. The applicability of a 1,2,3-triazole ring as a replacement of sugar [17][18][19] or nucleobase moieties 17,[19][20][21] as well as an additional linker between a phosphonoalkyl unit and a nucleobase has been widely explored [22][23][24][25][26][27][28] including our achievements.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, antiviral and cytostatic activity of ω-(1H-1,2,3-triazol-1-yl)(polyhydroxy)alkylphosphonates as acyclic nucleotide analogues

Głowacka

Balzarini

Andrei

et al. 2014

Bioorganic & Medicinal Chemistry

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The efficient synthesis of a new series of polyhydroxylated dibenzyl ω-(1H-1,2,3-triazol-1-yl)alkylphosphonates as acyclic nucleotide analogues is described starting from dibenzyl ω-azido(polyhydroxy)alkylphosphonates and selected alkynes under microwave irradiation. Selected O,O-dibenzylphosphonate acyclonucleotides were transformed into the respective phosphonic acids. All compounds were evaluated in vitro for activity against a broad variety of DNA and RNA viruses and for cytostatic activity against murine leukemia L1210, human T-lymphocyte CEM and human cervix carcinoma HeLa cells. Compound (1S,2S)-16b exhibited antiviral activity against Influenza A H3N2 subtype (EC50=20μM-visual CPE score; EC50=18μM-MTS method; MCC >100μM, CC50 >100μM) in Madin Darby canine kidney cell cultures (MDCK), and (1S,2S)-16k was active against vesicular stomatitis virus and respiratory syncytial virus in HeLa cells (EC50=9 and 12μM, respectively). Moreover, compound (1R,2S)-16l showed activity against both herpes simplex viruses (HSV-1, HSV-2) in HEL cell cultures (EC50=2.9 and 4μM, respectively) and feline herpes virus in CRFK cells (EC50=4μM) but at the same time it exhibited cytotoxicity toward uninfected cell (MCC⩾4μM). Several other compounds have been found to inhibit proliferation of L1210, CEM as well as HeLa cells with IC50 in the 4-50μM range. Among them compounds (1S,2S)- and (1R,2S)-16l were the most active (IC50 in the 4-7μM range).

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Section: Introductionmentioning

confidence: 99%

Design, synthesis, antiviral and cytostatic activity of ω-(1H-1,2,3-triazol-1-yl)(polyhydroxy)alkylphosphonates as acyclic nucleotide analogues

Głowacka

Balzarini

Andrei

et al. 2014

Bioorganic & Medicinal Chemistry

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“…On the other hand, nucleoside analogues as antiviral chemotherapeutic agents have been comprehensively described in the literature [8][9][10], and many of these analogues were synthesized recently as antiviral agents [10][11][12]. Moreover, C-nucleosides were reported to be of great value from the biological point of view [13,14], and many of their derivatives have been synthesized as potential antibacterial [15], antifungal agents [16,17] and were tested also against herpes simplex viruses (HSV-1 and HSV-2) [13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and anti-HSV-1 evaluation of some pyrazoles and fused pyrazolopyrimidines

Rashad

Hegab

Abdel-Megeid

et al. 2009

European Journal of Medicinal Chemistry

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“…The structure of 7 was established Downloaded by [Johns Hopkins University] at 17:49 03 January 2015 from its 1 H NMR spectrum, which showed a singlet signal for H-5 at δ 8.06 in agreement with the formation of the 4-methylene 1,2,3-triazole derivative 7. [14,18,19] SCHEME 2…”

Section: Resultsmentioning

confidence: 99%

Synthesis of AZT analogues: 7-(3-azido-2hydroxypropyl)-, 7-(3-amino-2-hydroxypropyl)-, 7-(3-triazolyl-2-hydroxypropyl)theophyllines

Ashry

Abdel‐Rahman

Rashed

et al. 2006

Nucleosides, Nucleotides & Nucleic Acids

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Nucleophilic displacement of the tosyloxy group in 7-(2-hydroxy-3-p-toluenesulfonyloxypropyl)theophylline (1) with azide anion afforded 7-(3-azido-2-hydroxypropyl)theophylline (2). Reduction of the 3-azido group in 2 with Ph3P/Py/NH4OH afforded the 3-amino derivative 4, alternatively obtained by regioselective amination of 7-(2,3-epoxypropyl)theophylline (3). Selective acetylation of 4 gave the N-acetyl derivative 5. 1,3-Dipolar cycloaddition of the azide group in 2 with N1-propargyl thymine (6) afforded the regioisomeric triazole 7.

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Synthesis of New 1,2,3-Triazole Acyclonucleoside Analogues of ACV and HBG

Cited by 20 publications

References 10 publications

Design, synthesis, antiviral and cytostatic activity of ω-(1H-1,2,3-triazol-1-yl)(polyhydroxy)alkylphosphonates as acyclic nucleotide analogues

Design, synthesis, antiviral and cytostatic activity of ω-(1H-1,2,3-triazol-1-yl)(polyhydroxy)alkylphosphonates as acyclic nucleotide analogues

Synthesis and anti-HSV-1 evaluation of some pyrazoles and fused pyrazolopyrimidines

Synthesis of AZT analogues: 7-(3-azido-2hydroxypropyl)-, 7-(3-amino-2-hydroxypropyl)-, 7-(3-triazolyl-2-hydroxypropyl)theophyllines

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