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

Synthesis of pyrrolo [2, 3-d] pyrimidine nucleoside derivatives as potential anti-HCV agents

CVNS Varaprasad, KS Ramasamy, JL Girardet…

Index: Varaprasad, Chamakura V.N.S.; Ramasamy, Kanda S.; Girardet, Jean-Luc; Gunic, Esmir; Lai, Vicky; Zhong, Weidong; An, Haoyun; Hong, Zhi Bioorganic Chemistry, 2007 , vol. 35, # 1 p. 25 - 34

Full Text: HTML

Citation Number: 39

Abstract

Several Toyocamycin (4) analogues were examined for their ability to inhibit HCV RNA in a replicon assay. Among the compounds examined 4-methylthio (18) and 5-carboxamide oxime derivatives (23 and 27) of Toyocamycin were found to have good activity and selectivity.

Jaspamycin Structure

~%

1H-Pyrrolo[2,3-d]pyrimidine-5-carboximidamide,4,7-dihydro-N-hydroxy-4-oxo-7-b-D-ribofuranosyl- Structure

1H-Pyrrolo[2,3-...

4-chloro-5-cyano-7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine Structure

4-chloro-5-cyan...

~81%

5-chloro-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene-7-carbonitrile Structure

5-chloro-9-[3,4...

3,4-dihydro-4-oxo-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile Structure

3,4-dihydro-4-o...

~%

5-chloro-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene-7-carbonitrile Structure

5-chloro-9-[3,4...

Toyocamycin Structure

~%

5-chloro-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene-7-carbonitrile Structure

5-chloro-9-[3,4...

Jaspamycin Structure

~%

5-chloro-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene-7-carbonitrile Structure

5-chloro-9-[3,4...

5-chloro-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene-7-carbonitrile Structure

5-chloro-9-[3,4...

Sodium thiomethoxide Structure

Sodium thiomethoxide

~73%

9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylsulfanyl-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene-7-carbonitrile Structure

9-[3,4-dihydrox...

3,4-dihydro-4-oxo-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile Structure

3,4-dihydro-4-o...

~%

9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylsulfanyl-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene-7-carbonitrile Structure

9-[3,4-dihydrox...

4-chloro-5-cyano-7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine Structure

4-chloro-5-cyan...

~%

9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylsulfanyl-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene-7-carbonitrile Structure

9-[3,4-dihydrox...

Jaspamycin Structure

~%

9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylsulfanyl-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene-7-carbonitrile Structure

9-[3,4-dihydrox...

Jaspamycin Structure

~%

1H-Pyrrolo[2,3-d]pyrimidine-5-carboximidamide,4,7-dihydro-4-oxo-7-b-D-ribofuranosyl- Structure

1H-Pyrrolo[2,3-...

1H-Pyrrolo[2,3-d]pyrimidine-5-carboximidamide,4,7-dihydro-N-hydroxy-4-oxo-7-b-D-ribofuranosyl- Structure

1H-Pyrrolo[2,3-...

~%

1H-Pyrrolo[2,3-d]pyrimidine-5-carboximidamide,4,7-dihydro-4-oxo-7-b-D-ribofuranosyl- Structure

1H-Pyrrolo[2,3-...

Jaspamycin Structure

~%

1H-Pyrrolo[2,3-d]pyrimidine-5-carbothioamide,4,7-dihydro-4-oxo-7-b-D-ribofuranosyl- Structure

1H-Pyrrolo[2,3-...

Jaspamycin Structure

~%

1H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide,4,7-dihydro-4-oxo-7-b-D-ribofuranosyl- Structure

1H-Pyrrolo[2,3-...

Sodium Methylate Structure

Sodium Methylate

5-chloro-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene-7-carbonitrile Structure

5-chloro-9-[3,4...

~51%

9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methoxy-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene-7-carbonitrile Structure

9-[3,4-dihydrox...

3,4-dihydro-4-oxo-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile Structure

3,4-dihydro-4-o...

~%

9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methoxy-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene-7-carbonitrile Structure

9-[3,4-dihydrox...

4-chloro-5-cyano-7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine Structure

4-chloro-5-cyan...

~%

9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methoxy-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene-7-carbonitrile Structure

9-[3,4-dihydrox...

Jaspamycin Structure

~%

9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methoxy-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene-7-carbonitrile Structure

9-[3,4-dihydrox...