Straightforward synthesis of triazoloacyclonucleotide phosphonates as potential HCV inhibitors

Elayadi, Hanane; Smietana, Michaël; Pannecouque, Christophe; Leyssen, Pieter; Neyts, Johan; Vasseur, Jean‐Jacques; Lazrek, H. B.

doi:10.1016/j.bmcl.2010.10.046

Cited by 49 publications

(23 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…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%

“…[29][30][31][32][33][34][35] Recently, several http://dx.doi.org/10.1016/j.bmc.2014.05.020 0968-0896/Ó 2014 Elsevier Ltd. All rights reserved. 25 Recently, we succeeded in the synthesis of 1-(3-phosphonopropyl)-1,2,3-triazole 13 substituted with benzoylbenzuracil via a methylene linker which exhibited activity against herpes simplex virus-1 (KOS), herpes simplex virus-2 (G) and feline herpes virus. 2).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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

View full text Add to dashboard Cite

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).

show abstract

Section: Introductionmentioning

confidence: 99%

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

View full text Add to dashboard Cite

show abstract

“…Monopropargyl pyrimidine nucleobases (uracil and thymine) are versatile building blocks for the synthesis of biologically relevant 1,2,3-triazoles [11]. They are generally used as starting material for the synthesis of triazole nucleosides [12][13][14][15][16][17][18][19], triazole nucleotides [20][21][22][23], oxiconazole analogues [24], nucleopeptides [25], inhibitors of human topoisomerase type II [26], and nucleoamino oxyacids [27]. Further, these propargyl nucleobases are also used in the synthesis of organogels [28], and as corrosion inhibitors [29].…”

Section: Introductionmentioning

confidence: 99%

Multicomponent Click Synthesis of New 1,2,3-Triazole Derivatives of Pyrimidine Nucleobases: Promising Acidic Corrosion Inhibitors for Steel

et al. 2013

View full text Add to dashboard Cite

A series of new mono-1,2,3-triazole derivatives of pyrimidine nucleobases were synthesized by one-pot copper(I)-catalyzed 1,3-dipolar cycloaddition reactions between N-1-propargyluracil and thymine, sodium azide and several benzyl halides. The desired heterocyclic compounds were obtained in good yields and characterized by NMR, IR, and high resolution mass spectrometry. These compounds were investigated as corrosion inhibitors for steel in 1 M HCl solution, using electrochemical impedance spectroscopy (EIS) technique. The results indicate that these heterocyclic compounds are promising acidic corrosion inhibitors for steel.

show abstract

“…68 objavili su sintezu modificiranih struktura poznatih antivirusnih spojeva primjenom 1,3-dipolarne cikloadicije. Autori su unutar acikličkog supstituenta ugradili triazolni prsten, čime su fleksibilnost strukture dodatno ograničili (slika 5).…”

Section: Modifikacije Nukleozida U Domeni šEćera I Nukleozidni Biokonunclassified

1,3-Dipolarna cikloadicija (I. dio): Dobivanje 1,2,3-triazolnih derivata u nukleozidnoj kemiji

et al. 2015

View full text Add to dashboard Cite

et al.: 1,3-Dipolarna cikloadicija (I. dio): Dobivanje 1,2,3-triazolnih derivata…, (2015) 481−498 Uvod Kada je 1953. godine obznanjen model DNA s dvostrukom uzvojnicom te objašnjen princip genetskog koda i uloga nukleinskih kiselina u stanicama, ispitivanje biološke aktivnosti nukleozida i njihovih fosforiliranih derivata postalo je fundamentalno i neiscrpno područje znanstvenog interesa. Prvi radovi iz ovog područja bili su usredotočeni na transformaciju nukleobaze vezane na neki šećer ili je transformacija provedena samo na šećernoj komponenti prirodnog nukleozida. Tek 1974. godine otkrićem prvog primjenjivog antivirusnog lijeka aciklovira 1 interes se proši-rio i na spojeve u kojima se nukleobaza i šećerna komponenta značajno razlikuju od prirodnih struktura te je otkriveno da neki od njih imaju antitumorsku, antivirusnu i/ili antibakterijsku aktivnost.U potrazi za novim biološki aktivnim nukleozidnim derivatima razvijene su brojne metode njihove sinteze. Tako je posljednjih godina intenzivno razvijeno područje primjene paladijem kataliziranih reakcija adicija i supstitucija (Richard F. Heck, Ei-ichi Negishi i Akira Suzuki; Nobelova nagrada za kemiju 2010. godine). Još šezdesetih godina prošlog stoljeća otkrivena je Heckova reakcija 2,3,4 stvaranja veze ugljik-ugljik, ali je njezina primjena intenzivirana tek osamdesetih godina kada su Bergstrom i sur. objavili nekoliko radova u kojima opisuju reakcije povezivanja nukleozida s alilnim halogenidima, 5 olefinskim spojevima, 6 alkoholima i acetatima. 7 Druga metoda Pd(0)-katalizirane reakcije alkiliranja, tzv. Tsuji-Trostova reakcija, također je pokazala velik potencijal zbog široke primjene i relativno jednostavnih reakcijskih uvjeta. 3Paladijem katalizirane reakcije mogu se provoditi i s različi-tim organometalnim spojevima kao što su organokositrovi (Stille), 3,8 organocinkovi (Negishi), 9 organosilicijevi (Hiyama) 10 ili organoborovi spojevi (Suzuki). 3Osnovni razlog za veliku upotrebu paladija u sintezi je to što se stvaranjem nove veze ugljik-ugljik pruža mogućnost novih strukturnih transformacija molekule. U tablici 1 prikazane su najčešće paladijem katalizirane reakcije povezivanja primijenjene u kemiji nukleozida.Osim što su primjenom paladijem kataliziranih reakcija pripravljeni mnogi biološki aktivni derivati nukleobaza/ nukleozida, takvi spojevi mogu biti i prekursori drugih interesantnih derivata u brojnim reakcijama. U ovom radu bit će prikazane primjene različitih alkinilnih derivata nukleobaza/nukleozida (pripravljenih paladijem kataliziranim reakcijama) u 1,3-dipolarnoj cikloadicijskoj reakciji s azidima u reakcijskim uvjetima koji omogućuju dobivanje 1,2,3-triazolnih specija. Klik-kemijaPojam klik-kemije prvi su put upotrijebili Sharpless i sur. 2001. godine, 11 a nedvojbeno predstavlja jedan od najpopularnijih pristupa u suvremenoj organskoj sintezi.12 Njime su objedinili široku paletu kemijskih reakcija nastajanja veze ugljik-heteroatom u kojima se brzo i pouzdano dolazi do produkata spajanjem više manjih jedinica. Postoji ne-1,3-Dipol...

show abstract

Straightforward synthesis of triazoloacyclonucleotide phosphonates as potential HCV inhibitors

Cited by 49 publications

References 32 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

Multicomponent Click Synthesis of New 1,2,3-Triazole Derivatives of Pyrimidine Nucleobases: Promising Acidic Corrosion Inhibitors for Steel

1,3-Dipolarna cikloadicija (I. dio): Dobivanje 1,2,3-triazolnih derivata u nukleozidnoj kemiji

Contact Info

Product

Resources

About