e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis of halogen-substituted 3-deazaadenosine and 3-deazaguanosine analogues as potential antitumor/antiviral agents

…, DE Mozdziesz, TS Lin† 1, GE Dutschman…

Index: Liu; Luo; Mozdziesz; Lin; Dutschman; Gullen; Cheng; Sartorelli Nucleosides, Nucleotides and Nucleic Acids, 2001 , vol. 20, # 12 p. 1975 - 2000

Full Text: HTML

Citation Number: 20

Abstract

Various 2-halogen-substituted analogues (38, 39, 43 and 44), 3-halogen-substituted analogues (51 and 52), and 2′, 3′-dihalogen-substituted analogues (57–60) of 3- deazaadenosine and 3-halogen-substituted analogues (61 and 62) of 3-deazaguanosine have been synthesized as potential anticancer and/or antiviral agents. Among these compounds, 3-deaza-3-bromoguanosine (62) showed significant cytotoxicity against ...

2-Chloro-5-fluoro-4-pyridinamine Structure

2-Chloro-5-fluo...

~83%

N-(2-chloro-5-fluoropyridin-4-yl)nitramide Structure

N-(2-chloro-5-f...

2-Chloro-5-fluoropyridine Structure

2-Chloro-5-fluo...

~%

N-(2-chloro-5-fluoropyridin-4-yl)nitramide Structure

N-(2-chloro-5-f...

2-CHLORO-5-FLUOROPYRIDINE 1-OXIDE Structure

2-CHLORO-5-FLUO...

~%

N-(2-chloro-5-fluoropyridin-4-yl)nitramide Structure

N-(2-chloro-5-f...

2-CHLORO-5-FLUORO-4-NITROPYRIDINE 1-OXIDE Structure

2-CHLORO-5-FLUO...

~%

N-(2-chloro-5-fluoropyridin-4-yl)nitramide Structure

N-(2-chloro-5-f...

N/A Structure

~91%

2,6-Difluoro-3-nitropyridin-4-amine Structure

2,6-Difluoro-3-...

1-Amino-2,6-dichloro-3,5-difluorobenzene Structure

1-Amino-2,6-dic...

~%

2,6-Difluoro-3-nitropyridin-4-amine Structure

2,6-Difluoro-3-...

3,5-Dichloro-2,4,6-trifluoropyridine Structure

3,5-Dichloro-2,...

~%

2,6-Difluoro-3-nitropyridin-4-amine Structure

2,6-Difluoro-3-...

4-Amino-2,6-difluoropyridine Structure

4-Amino-2,6-dif...

~%

2,6-Difluoro-3-nitropyridin-4-amine Structure

2,6-Difluoro-3-...

4-Amino-2,6-difluoropyridine Structure

4-Amino-2,6-dif...

~%

3,5-difluoro-4,7,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene Structure

3,5-difluoro-4,...

2,6-Difluoro-3-nitropyridin-4-amine Structure

2,6-Difluoro-3-...

~%

3,5-difluoro-4,7,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene Structure

3,5-difluoro-4,...

1-Amino-2,6-dichloro-3,5-difluorobenzene Structure

1-Amino-2,6-dic...

~%

3,5-difluoro-4,7,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene Structure

3,5-difluoro-4,...

3,5-Dichloro-2,4,6-trifluoropyridine Structure

3,5-Dichloro-2,...

~%

3,5-difluoro-4,7,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene Structure

3,5-difluoro-4,...

N/A Structure

~%

3,5-difluoro-4,7,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene Structure

3,5-difluoro-4,...

1-[(1-acetyloxy-1-ethoxy)methyl]-4,6-difluoroimidazo[4,5-c]pyridine Structure

1-[(1-acetyloxy...

~%

3,5-difluoro-4,7,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene Structure

3,5-difluoro-4,...

2,6-difluoropyridine-3,4-diamine Structure

2,6-difluoropyr...

~%

3,5-difluoro-4,7,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene Structure

3,5-difluoro-4,...

Diethoxymethyl acetate Structure

Diethoxymethyl ...

2,6-difluoropyridine-3,4-diamine Structure

2,6-difluoropyr...

~90%

3,5-difluoro-4,7,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene Structure

3,5-difluoro-4,...

1-[(1-acetyloxy-1-ethoxy)methyl]-4,6-difluoroimidazo[4,5-c]pyridine Structure

1-[(1-acetyloxy...

3,5-Dichloro-2,4,6-trifluoropyridine Structure

3,5-Dichloro-2,...

~%

3-Chloro-2,6-difluoropyridin-4-amine Structure

3-Chloro-2,6-di...

2,6-Difluoro-3-nitropyridin-4-amine Structure

2,6-Difluoro-3-...

~93%

2,6-difluoropyridine-3,4-diamine Structure

2,6-difluoropyr...

4-Amino-2,6-difluoropyridine Structure

4-Amino-2,6-dif...

~%

2,6-difluoropyridine-3,4-diamine Structure

2,6-difluoropyr...

1-Amino-2,6-dichloro-3,5-difluorobenzene Structure

1-Amino-2,6-dic...

~%

2,6-difluoropyridine-3,4-diamine Structure

2,6-difluoropyr...

3,5-Dichloro-2,4,6-trifluoropyridine Structure

3,5-Dichloro-2,...

~%

2,6-difluoropyridine-3,4-diamine Structure

2,6-difluoropyr...

N/A Structure

~%

2,6-difluoropyridine-3,4-diamine Structure

2,6-difluoropyr...

2,5-Dichloro-pyridine 1-oxide Structure

2,5-Dichloro-py...

~52%

2,5-Dichloro-4-nitropyridine 1-oxide Structure

2,5-Dichloro-4-...

2,5-Dichloropyridine Structure

2,5-Dichloropyridine

~%

2,5-Dichloro-4-nitropyridine 1-oxide Structure

2,5-Dichloro-4-...

2,3,6-trifluoropyridin-4-amine Structure

2,3,6-trifluoro...

~%

2,5,6-trifluoropyridine-3,4-diamine Structure

2,5,6-trifluoro...

3-chloro-2,5,6-trifluoropyridin-4-amine Structure

3-chloro-2,5,6-...

~%

2,5,6-trifluoropyridine-3,4-diamine Structure

2,5,6-trifluoro...

3-Chlorotetrafluoropyridine Structure

3-Chlorotetrafl...

~%

2,5,6-trifluoropyridine-3,4-diamine Structure

2,5,6-trifluoro...

4-nitramino-2,3,6-trifluoropyridine Structure

4-nitramino-2,3...

~%

2,5,6-trifluoropyridine-3,4-diamine Structure

2,5,6-trifluoro...

3,5-Dichloro-2,4,6-trifluoropyridine Structure

3,5-Dichloro-2,...

~98%

1-Amino-2,6-dichloro-3,5-difluorobenzene Structure

1-Amino-2,6-dic...

3-Chlorotetrafluoropyridine Structure

3-Chlorotetrafl...

~%

2,3,6-trifluoropyridin-4-amine Structure

2,3,6-trifluoro...

3-chloro-2,5,6-trifluoropyridin-4-amine Structure

3-chloro-2,5,6-...

~%

2,3,6-trifluoro-5-nitropyridin-4-amine Structure

2,3,6-trifluoro...

3-Chlorotetrafluoropyridine Structure

3-Chlorotetrafl...

~%

2,3,6-trifluoro-5-nitropyridin-4-amine Structure

2,3,6-trifluoro...

2,3,6-trifluoropyridin-4-amine Structure

2,3,6-trifluoro...

~%

2,3,6-trifluoro-5-nitropyridin-4-amine Structure

2,3,6-trifluoro...

2,5-dichloro-3-nitropyridin-4-amine Structure

2,5-dichloro-3-...

~91%

2,5-dichloropyridine-3,4-diamine Structure

2,5-dichloropyr...

2,5-Dichloropyridine Structure

2,5-Dichloropyridine

~%

2,5-dichloropyridine-3,4-diamine Structure

2,5-dichloropyr...

2,5-Dichloro-4-pyridinamine Structure

2,5-Dichloro-4-...

~%

2,5-dichloropyridine-3,4-diamine Structure

2,5-dichloropyr...

2,5-Dichloro-pyridine 1-oxide Structure

2,5-Dichloro-py...

~%

2,5-dichloropyridine-3,4-diamine Structure

2,5-dichloropyr...

2,5-Dichloro-4-nitropyridine 1-oxide Structure

2,5-Dichloro-4-...

~%

2,5-dichloropyridine-3,4-diamine Structure

2,5-dichloropyr...

N/A Structure

~%

2,5-dichloropyridine-3,4-diamine Structure

2,5-dichloropyr...

2-Chloro-5-fluoro-3-nitropyridin-4-amine Structure

2-Chloro-5-fluo...

~93%

2-Chloro-5-fluoropyridine-3,4-diamine Structure

2-Chloro-5-fluo...

N-(2-chloro-5-fluoropyridin-4-yl)nitramide Structure

N-(2-chloro-5-f...

~%

2-Chloro-5-fluoropyridine-3,4-diamine Structure

2-Chloro-5-fluo...

1-[(1-acetyloxy-1-ethoxy)methyl]-4,6,7-trifluoroimidazo[4,5-c]pyridine Structure

1-[(1-acetyloxy...

~%

4,6,7-trifluoro-3H-imidazo[4,5-c]pyridine Structure

4,6,7-trifluoro...

2,3,6-trifluoropyridin-4-amine Structure

2,3,6-trifluoro...

~%

4,6,7-trifluoro-3H-imidazo[4,5-c]pyridine Structure

4,6,7-trifluoro...

3-chloro-2,5,6-trifluoropyridin-4-amine Structure

3-chloro-2,5,6-...

~%

4,6,7-trifluoro-3H-imidazo[4,5-c]pyridine Structure

4,6,7-trifluoro...

3-Chlorotetrafluoropyridine Structure

3-Chlorotetrafl...

~%

4,6,7-trifluoro-3H-imidazo[4,5-c]pyridine Structure

4,6,7-trifluoro...

4-nitramino-2,3,6-trifluoropyridine Structure

4-nitramino-2,3...

~%

4,6,7-trifluoro-3H-imidazo[4,5-c]pyridine Structure

4,6,7-trifluoro...

2,3,6-trifluoro-5-nitropyridin-4-amine Structure

2,3,6-trifluoro...

~%

4,6,7-trifluoro-3H-imidazo[4,5-c]pyridine Structure

4,6,7-trifluoro...

2,5,6-trifluoropyridine-3,4-diamine Structure

2,5,6-trifluoro...

~%

4,6,7-trifluoro-3H-imidazo[4,5-c]pyridine Structure

4,6,7-trifluoro...

Diethoxymethyl acetate Structure

Diethoxymethyl ...

2,5,6-trifluoropyridine-3,4-diamine Structure

2,5,6-trifluoro...

~46%

4,6,7-trifluoro-3H-imidazo[4,5-c]pyridine Structure

4,6,7-trifluoro...

1-[(1-acetyloxy-1-ethoxy)methyl]-4,6,7-trifluoroimidazo[4,5-c]pyridine Structure

1-[(1-acetyloxy...

3-chloro-2,6-difluoro-4-nitraminopyridine Structure

3-chloro-2,6-di...

~82%

3-chloro-2,6-difluoro-5-nitropyridin-4-amine Structure

3-chloro-2,6-di...

1-Amino-2,6-dichloro-3,5-difluorobenzene Structure

1-Amino-2,6-dic...

~%

3-chloro-2,6-difluoro-5-nitropyridin-4-amine Structure

3-chloro-2,6-di...

3,5-Dichloro-2,4,6-trifluoropyridine Structure

3,5-Dichloro-2,...

~%

3-chloro-2,6-difluoro-5-nitropyridin-4-amine Structure

3-chloro-2,6-di...

3-Chloro-2,6-difluoropyridin-4-amine Structure

3-Chloro-2,6-di...

~%

3-chloro-2,6-difluoro-5-nitropyridin-4-amine Structure

3-chloro-2,6-di...

2,5-Dichloro-4-nitropyridine 1-oxide Structure

2,5-Dichloro-4-...

~85%

2,5-Dichloro-4-pyridinamine Structure

2,5-Dichloro-4-...

2,5-Dichloropyridine Structure

2,5-Dichloropyridine

~%

2,5-Dichloro-4-pyridinamine Structure

2,5-Dichloro-4-...

2,5-Dichloro-pyridine 1-oxide Structure

2,5-Dichloro-py...

~%

2,5-Dichloro-4-pyridinamine Structure

2,5-Dichloro-4-...

N/A Structure

~97%

2,5-dichloro-3-nitropyridin-4-amine Structure

2,5-dichloro-3-...

2,5-Dichloropyridine Structure

2,5-Dichloropyridine

~%

2,5-dichloro-3-nitropyridin-4-amine Structure

2,5-dichloro-3-...

2,5-Dichloro-pyridine 1-oxide Structure

2,5-Dichloro-py...

~%

2,5-dichloro-3-nitropyridin-4-amine Structure

2,5-dichloro-3-...

2,5-Dichloro-4-nitropyridine 1-oxide Structure

2,5-Dichloro-4-...

~%

2,5-dichloro-3-nitropyridin-4-amine Structure

2,5-dichloro-3-...

2,5-Dichloro-4-pyridinamine Structure

2,5-Dichloro-4-...

~%

2,5-dichloro-3-nitropyridin-4-amine Structure

2,5-dichloro-3-...

2-Chloro-5-fluoropyridine Structure

2-Chloro-5-fluo...

~%

2-CHLORO-5-FLUORO-4-NITROPYRIDINE 1-OXIDE Structure

2-CHLORO-5-FLUO...

2-Chloro-5-fluoropyridine Structure

2-Chloro-5-fluo...

~%

4-Chloro-7-fluoro-1H-imidazo[4,5-c]pyridine Structure

4-Chloro-7-fluo...

2-CHLORO-5-FLUOROPYRIDINE 1-OXIDE Structure

2-CHLORO-5-FLUO...

~%

4-Chloro-7-fluoro-1H-imidazo[4,5-c]pyridine Structure

4-Chloro-7-fluo...

2-Chloro-5-fluoro-4-pyridinamine Structure

2-Chloro-5-fluo...

~%

4-Chloro-7-fluoro-1H-imidazo[4,5-c]pyridine Structure

4-Chloro-7-fluo...

N-(2-chloro-5-fluoropyridin-4-yl)nitramide Structure

N-(2-chloro-5-f...

~%

4-Chloro-7-fluoro-1H-imidazo[4,5-c]pyridine Structure

4-Chloro-7-fluo...

2-CHLORO-5-FLUORO-4-NITROPYRIDINE 1-OXIDE Structure

2-CHLORO-5-FLUO...

~%

4-Chloro-7-fluoro-1H-imidazo[4,5-c]pyridine Structure

4-Chloro-7-fluo...

2-Chloro-5-fluoro-3-nitropyridin-4-amine Structure

2-Chloro-5-fluo...

~%

4-Chloro-7-fluoro-1H-imidazo[4,5-c]pyridine Structure

4-Chloro-7-fluo...

1-[(1-acetyloxy-1-ethoxy)methyl]-4-chloro-7-fluoroimidazo[4,5-c]pyridine Structure

1-[(1-acetyloxy...

~%

4-Chloro-7-fluoro-1H-imidazo[4,5-c]pyridine Structure

4-Chloro-7-fluo...

2-Chloro-5-fluoropyridine-3,4-diamine Structure

2-Chloro-5-fluo...

~%

4-Chloro-7-fluoro-1H-imidazo[4,5-c]pyridine Structure

4-Chloro-7-fluo...

Diethoxymethyl acetate Structure

Diethoxymethyl ...

2-Chloro-5-fluoropyridine-3,4-diamine Structure

2-Chloro-5-fluo...

~79%

4-Chloro-7-fluoro-1H-imidazo[4,5-c]pyridine Structure

4-Chloro-7-fluo...

1-[(1-acetyloxy-1-ethoxy)methyl]-4-chloro-7-fluoroimidazo[4,5-c]pyridine Structure

1-[(1-acetyloxy...