Synthesis and antiviral activity of 3'-heterocyclic substituted 3'-deoxythymidines

P Wigerinck, A Van Aerschot, G Janssen…

Index: Wigerinck, Piet; Aerschot, Arthur Van; Janssen, Gerard; Claes, Paul; Balzarini, Jan; et al. Journal of Medicinal Chemistry, 1990 , vol. 33, # 2 p. 868 - 873

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Citation Number: 33

Abstract

Various 3 '-deoxythymidine analogues with an heterocyclic five-membered ring in the 3'- erythro position have been synthesized. The pyrrol-1-yl (3) and the 1, 2, 4-triazol-4-yl (5) compounds were synthesized from 1-(3-amino-2, 3-dideoxy-@-D-erythro-pentofuranosy1) thymine. The pyrazol-1-yl (16a), imidazol-l-y1 (16b), and 1, 2, 4-triazol-l-y1 (16c) derivatives were obtained by epoxide opening of the corresponding 1-(2, 3-anhydro-@-~-l~ o~~~ yl) ...

 Related Synthetic Route
1-(5-O-trityl-3-imidazol-1-yl-3-deoxy-β-D-arabinofuranosyl)thymine Structure

124355-30-2

1-(5-O-trityl-3...

~87%

1-[(2R,3S,4S,5S)-3-hydroxy-5-(hydroxymethyl)-4-imidazol-1-yloxolan-2-yl]-5-methylpyrimidine-2,4-dione Structure

124355-31-3

1-[(2R,3S,4S,5S...

5-methyl-1-[(2R,4R)-4-(trityloxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]pyrimidine-2,4-dione Structure

115913-84-3

5-methyl-1-[(2R...

~%

1-[(2R,3S,4S,5S)-3-hydroxy-5-(hydroxymethyl)-4-imidazol-1-yloxolan-2-yl]-5-methylpyrimidine-2,4-dione Structure

124355-31-3

1-[(2R,3S,4S,5S...

1,2-Diformylhydrazine Structure

628-36-4

1,2-Diformylhyd...

3'-Amino-3'-deoxythymidine Structure

52450-18-7

3'-Amino-3'-deo...

~92%

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

123533-11-9

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

N-((2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)acetamide Structure

124355-26-6

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

~%

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

123533-11-9

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

N/A Structure

124355-25-5

N/A

~%

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

123533-11-9

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

Zidovudine Structure

30516-87-1

Zidovudine

Benzoyl chloride Structure

98-88-4

Benzoyl chloride

~89%

5'-O-BENZOYL-3'-AZIDO-3'-DEOXYTHYMIDINE Structure

106060-78-0

5'-O-BENZOYL-3'...

1-(5-O-trityl-3-(1,2,4-triazol-1-yl)-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine Structure

124355-37-9

1-(5-O-trityl-3...

~72%

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

124355-38-0

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

5-methyl-1-[(2R,4R)-4-(trityloxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]pyrimidine-2,4-dione Structure

115913-84-3

5-methyl-1-[(2R...

~%

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

124355-38-0

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

N/A Structure

124355-32-4

N/A

~%

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

124355-38-0

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

1-(5-O-trityl-3-(1,2,4-triazol-1-yl)-2-O-(phenoxythionocarbonyl)-3-deoxy-β-D-arabinofuranosyl)thymine Structure

124355-36-8

1-(5-O-trityl-3...

~%

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

124355-38-0

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

N/A Structure

124355-32-4

N/A

~79%

1-[(2R,3S,4S,5S)-3-hydroxy-5-(hydroxymethyl)-4-(1,2,4-triazol-1-yl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Structure

124355-34-6

1-[(2R,3S,4S,5S...

5-methyl-1-[(2R,4R)-4-(trityloxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]pyrimidine-2,4-dione Structure

115913-84-3

5-methyl-1-[(2R...

~%

1-[(2R,3S,4S,5S)-3-hydroxy-5-(hydroxymethyl)-4-(1,2,4-triazol-1-yl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Structure

124355-34-6

1-[(2R,3S,4S,5S...


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