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

Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides

…, A Van Aerschot, G Janssen, E De Clercq

Index: Herdewijn; Balzarini; Baba; Pauwels; Van Aerschot; Janssen; De Clerq Journal of Medicinal Chemistry, 1988 , vol. 31, # 10 p. 2040 - 2048

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Citation Number: 141

Abstract

However, this unsaturated guanosine derivative was not isolated nor characterized and its yield was very low. A structure-activity analysis is provided for several base-modified pyrimidine 3'-azido-2 ', 3 '-dideoxynucleosides (la, Id, le, If, lg) and compared with the previously described compounds lh and li. l0 Although some of these compounds (la, le, lh) were previously described by Lin et a1.: these authors only evaluated them against the ...

9-(2-O-mesyl-3-deoxy-β-D-erythro-pentofuranosyl)adenine Structure

9-(2-O-mesyl-3-...

~36%

[(2S,4S,5R)-5-(6-aminopurin-9-yl)-4-chlorooxolan-2-yl]methanol Structure

[(2S,4S,5R)-5-(...

N/A Structure

~%

2',3'-Didehydro-2',3'-dideoxyguanosine Structure

2',3'-Didehydro...

N/A Structure

~75%

1-[(2R,4S,5R)-5-(hydroxymethyl)-4-phenoxycarbothioyloxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione Structure

1-[(2R,4S,5R)-5...

((2S,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-azidotetrahydrofuran-2-yl)methyl benzoate Structure

((2S,3S,5R)-5-(...

~88%

3'-Azido-2',3'-dideoxyadenosine Structure

3'-Azido-2',3'-...

5'-O-benzoyl-3'-fluoro-2',3'-dideoxyguanosine Structure

5'-O-benzoyl-3'...

~74%

Lagociclovir Structure

Guanosine Structure

~%

Lagociclovir Structure

9-(5-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)guanine Structure

9-(5-O-benzoyl-...

~%

Lagociclovir Structure

2'-O-tosylguanosine Structure

2'-O-tosylguanosine

~%

Lagociclovir Structure

N2-acetyl-2'-O-tosyl-2,6-diamino-9-β-D-ribofuranosylpurine Structure

N2-acetyl-2'-O-...

~%

Lagociclovir Structure

9-(2-deoxy-α-L-erythro-pentofuranosyl)guanine Structure

9-(2-deoxy-α-L-...

~%

Lagociclovir Structure

2-Aminoadenosine Structure

2-Aminoadenosine

~%

Lagociclovir Structure

2'-Deoxyguanosine Structure

2'-Deoxyguanosine

~%

2',3'-Didehydro-2',3'-dideoxyguanosine Structure

2',3'-Didehydro...

N2,5'-O-bis(monomethoxytrityl)-2'-deoxyguanosine Structure

N2,5'-O-bis(mon...

~%

2',3'-Didehydro-2',3'-dideoxyguanosine Structure

2',3'-Didehydro...

9-(2-O-mesyl-3-deoxy-β-D-erythro-pentofuranosyl)adenine Structure

9-(2-O-mesyl-3-...

~36%

[(2S,4R,5R)-5-(6-aminopurin-9-yl)-4-bromooxolan-2-yl]methanol Structure

[(2S,4R,5R)-5-(...

9-(2-O-mesyl-3-deoxy-β-D-threo-pentofuranosyl)adenine Structure

9-(2-O-mesyl-3-...

~%

[(2S,4R,5R)-5-(6-aminopurin-9-yl)-4-bromooxolan-2-yl]methanol Structure

[(2S,4R,5R)-5-(...

5'-O-trityl-3'-(acetylthio)-2',3'-dideoxythymidine Structure

5'-O-trityl-3'-...

~67%

S-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] ethanethioate Structure

S-[(2R,3S,5R)-2...

3''-O-MESYL-5''-O-TRITYLTHYMIDINE Structure

3''-O-MESYL-5''...

~%

S-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] ethanethioate Structure

S-[(2R,3S,5R)-2...