Synthesis of 1′-C-Cyano Pyrimidine Nucleosides and Characterization as HCV Polymerase Inhibitors

Nucleosides, Nucleotides and Nucleic Acids

Volumn 34, Issue 11, 2015, Pages 763-785

  Kirschberg, Thorsten A ^a   Mish, Michael ^a   Squires, Neil H ^a   Zonte, Sebastian ^a   Aktoudianakis, Evangelos ^a   Metobo, Sammy ^a   Butler, Thomas ^a   Ju, Xie ^a   Cho, Aesop ^a   Ray, Adrian S ^a   Kim, Choung U ^b  

^a Medicinal Chemistry Department   (United States)

^b Kainos Medicine Inc   (South Korea)

Author keywords

1 cyano pyrimidine nucleosides; HCV; Nucleosides

Indexed keywords

1 3 (BENZOYLOXY) 5 CYANO 5 [2,4 DIOXO 3,4 DIHYDRO PYRIMIDIN 1(2H) YL] 4 HYDROXYTETRAHYDROFURAN 2 YL)ETHYL BENZOATE; 1 [ 3 (BENZOYLOXY) 5 CYANO 5 [2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 4 [(METHYLSULFONYL)OXY]TETRAHYDROFURAN 2 YL]ETHYL BENZOATE; 1 [3 (BENZOYLOXY) 5 CYANO 5 [2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 4 HYDROXYTETRAHYDROFURAN 2 YL]ETHYL BENZOATE; 1' C CYANO PYRIMIDINE NUCLEOSIDE; 2 [ 1 (BENZOYLOXY)ETHYL] 5 CYANO 5 [2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL]TETRAHYDROFURAN 3 YL BENZOATE; 2 [ 1 (BENZOYLOXY)ETHYL] 5 CYANOTETRAHYDROFURAN 3,4 DIYL DIBENZOATE; 2 [2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 3,4 DIHYDRO XY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 CARBONITRILE; 2 [2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 3,4 DIHYDROXY 5 ( 1 HYDROXYETHYL)TETRAHYDROFURAN 2 CARBONITRILE; 2 [2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 4 HYDROXY 5 (HYDROXYMETHYL) 3 METHOXYTETRAHYDROFURAN 2 CARBONITRILE; 2 [4 AMINO 2 OXOPYRIMIDIN 1(2H) YL] 3,4 DIHYDROXY 5 ( 1 HYDROXYETHYL)TETRAHYDROFURAN 2 CARBONITRILE; 2 [4 AMINO 2 OXOPYRIMIDIN 1(2H) YL] 3,4 DIHYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 CARBONITRILE; 2 [4 AMINO 2 OXOPYRIMIDIN 1(2H) YL] 4 HYDROXY 5 (HYDROXYMETHYL) 3 METHOXYTETRAHYDROFURAN 2 CARBONITRILE; 2 [4 AMINO 2 OXOPYRIMIDIN 1(2H) YL] 5 [ 1 (BENZOYLOXY)ETHYL] 2 CYANOTETRAHYDROFURAN 3,4 DIYL DIBENZOATE; 4 ACETOXY 5 [4 AMINO 2 OXOPYRIMIDIN 1(2H) YL] 2 [ 1 (BENZOYLOXY)ETHYL] 5 CYANOTETRAHYDROFURAN 3 YL BENZOATE; 4 [2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 6 ( 1 HYDROXYETHYL) 2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOLE 4 CARBONITRILE; 4 [2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 6 (HYDROXYMETHYL) 2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOLE 4 CARBONITRILE; 4 [2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 6 FORMYL 2,2 DIMETHYLTETRAHYDROFURO[3,4 D][1,3]DIOXOLE 4 CARBONITRILE; 5 [ 1 (BENZOYLOXY)ETHYL] 2 BROMO 2 CYANOTETRAHYDROFURAN 3,4 DIYL DIBENZOATE; 5 [ 1 (BENZOYLOXY)ETHYL] 2 CYANO 2 [2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL]TETRAHYDROFURAN 3,4 DIYL DIBENZOATE; 8 CYANO 8 [2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 2, 2,4,4 TETRAISOPROPYL 9 METHYLTETRAHYDRO 6H FURO[3,2 F][1,3,5,2,4] TRIOXADISILOCIN 9 YL METHYL OXALATE; 8 [2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 2,2,4,4 TETRAISOPROPYL 9 METHOXYTETRAHYDRO 6H FURO[3,2 F][1,3,5,2,4]TRIOXADISILOCINE 8 CARBONITRILE; 8 [2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 2,2,4,4 TETRAISOPROPYL 9 METHYLTETRAHYDRO 6H FURO[3,2 F][1,3,5,2,4]TRIOXADISILOCINE 8 CARBONITRILE; 8 [2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 9 HYDROXY 2,2,4,4 TETRAISOPROPYL 9 METHYLTETRAHYDRO 6H FURO[3,2 F][1,3,5,2,4] TRIOXADISILOCINE 8 CARBONITRILE; 8 [2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 9 HYDROXY 2,2,4,4 TETRAISOPROPYLTETRAHYDRO 6H FURO[3,2 F][1,3,5,2,4]TRIOXADISILOCINE 8 CARBONITRILE; 8 [4 AMINO 2 OXOPYRIMIDIN 1(2H) YL] 2,2,4,4 TETRAISOPROPYL 9 METHOXYTETRAHYDRO 6H FURO[3,2 F][1,3,5,2,4]TRIOXADISILOCINE 8 CARBONITRILE; 8 [4 ETHOXY 2 OXOPYRIMIDIN 1(2H) YL] 2,2,4,4 TETRAIS OPROPYL 9 METHOXYTETRAHYDRO 6H FURO[3,2 F][1,3,5,2,4]TRIOXADISILOCINE 8 CARBONITRILE; 8 [4 ETHOXY 2 OXOPYRIMIDIN 1(2H) YL] 9 HYDROXY 2,2,4,4 TETRAISOPROPYLTETRAHYDRO 6H FURO[3,2 F][1,3,5,2,4]TRIOXADISILOCINE 8 CARBONITRILE; ANTIVIRUS AGENT; PYRIMIDINE NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; DNA DIRECTED RNA POLYMERASE; ENZYME INHIBITOR; PYRIMIDINE NUCLEOSIDE;

ANTIVIRAL ACTIVITY; ARTICLE; CHIRALITY; DRUG PURIFICATION; DRUG SYNTHESIS; FOLLOW UP; HEPATITIS C VIRUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; METHYLATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY; STEREOISOMERISM; VIRUS REPLICATION; ANTAGONISTS AND INHIBITORS; CHEMISTRY; ENZYMOLOGY; HEPACIVIRUS; SYNTHESIS;

CHEMISTRY TECHNIQUES, SYNTHETIC; DNA-DIRECTED RNA POLYMERASES; ENZYME INHIBITORS; HEPACIVIRUS; PYRIMIDINE NUCLEOSIDES;

EID: 84946544634     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770.2015.1075550     Document Type: Article

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