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

Synthesis of certain [6: 5: 6] linear tricyclic nucleosides as potential antitumor agents

FL Chung, KH Schram, RP Panzica…

Index: Chung, Fung-Lung; Schram, Karl H.; Panzica, Raymond P.; Earl, Robert A.; Wotring, Linda L.; Townsend, Leroy B. Journal of Medicinal Chemistry, 1980 , vol. 23, # 11 p. 1158 - 1166

Full Text: HTML

Citation Number: 11

Abstract

A new class of tricyclic nucleosides in which the aglycon has a linear [6: 5: 6] geometry has been synthesized using certain pyrrolo [2, 3-d] pyrimidine nucleosides as the starting materials. An adenosine-adenosine analogue (12) has been prepared from 6- aminotoyocamycin using two different synthetic routes. An adenosine-guanosine analogue (4) and several adenosine-6-mercaptopurine ribonucleoside-type tricyclic nucleoside ...

sodium salt of 4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidin-5-one-7-thione Structure

sodium salt of ...

methyl iodide Structure

~72%

4-amino-7-(methylthio)-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidin-5-one Structure

4-amino-7-(meth...

4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine-5-thione Structure

4-amino-9-(β-D-...

allyl bromide Structure

~63%

5-(allylthio)-4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

5-(allylthio)-4...

5,8-diamino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene-7-carbothioamide Structure

5,8-diamino-9-[...

Ethyl formate Structure

~85%

4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine-5-thione Structure

4-amino-9-(β-D-...

5,8-diamino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene-7-carbothioamide Structure

5,8-diamino-9-[...

~%

5-(allylthio)-4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

5-(allylthio)-4...

5-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-mercapto-3,9-dihydro-4H-pyrrolo[2,3-d:5,4-d']dipyrimidin-4-one, ammonia salt Structure

5-amino-9-((2R,...

~%

4,7-diamino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidin-5-one Structure

4,7-diamino-9-(...

9H-Pyrrolo[2,3-d:5,4-d]dipyrimidin-4-amine, 5, 7-bis(methylthio)-9-.beta.-D-ribofuranosyl- Structure

9H-Pyrrolo[2,3-...

~68%

4,5-diamino-7-(methylthio)-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4,5-diamino-7-(...

4-amino-5-(methylthio)-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4-amino-5-(meth...

~89%

4,5-diamino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4,5-diamino-9-(...

4,5-diamino-7-(methylthio)-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4,5-diamino-7-(...

~44%

4,5-diamino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4,5-diamino-9-(...

5,8-diamino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene-7-carbothioamide Structure

5,8-diamino-9-[...

~%

4,5-diamino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4,5-diamino-9-(...

5,8-diamino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene-7-carbonitrile Structure

5,8-diamino-9-[...

~%

4,5-diamino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4,5-diamino-9-(...

4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine-5-thione Structure

4-amino-9-(β-D-...

~%

4,5-diamino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4,5-diamino-9-(...

9H-Pyrrolo[2,3-d:5,4-d]dipyrimidin-4-amine, 5, 7-bis(methylthio)-9-.beta.-D-ribofuranosyl- Structure

9H-Pyrrolo[2,3-...

~%

4,5-diamino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4,5-diamino-9-(...

Carbon disulphide Structure

Carbon disulphide

5,8-diamino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene-7-carbonitrile Structure

5,8-diamino-9-[...

~83%

4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine-5,7-dithione Structure

4-amino-9-(β-D-...

4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine-5-thione Structure

4-amino-9-(β-D-...

~94%

4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidin-5-one Structure

4-amino-9-(β-D-...

5-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-mercapto-3,9-dihydro-4H-pyrrolo[2,3-d:5,4-d']dipyrimidin-4-one, ammonia salt Structure

5-amino-9-((2R,...

~41%

4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidin-5-one Structure

4-amino-9-(β-D-...

5,8-diamino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene-7-carbothioamide Structure

5,8-diamino-9-[...

~%

4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidin-5-one Structure

4-amino-9-(β-D-...

4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine-5-thione Structure

4-amino-9-(β-D-...

methyl iodide Structure

~85%

4-amino-5-(methylthio)-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4-amino-5-(meth...

5,8-diamino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene-7-carbothioamide Structure

5,8-diamino-9-[...

~%

4-amino-5-(methylthio)-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4-amino-5-(meth...

5-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-mercapto-3,9-dihydro-4H-pyrrolo[2,3-d:5,4-d']dipyrimidin-4-one, ammonia salt Structure

5-amino-9-((2R,...

~61%

1H-Pyrrolo[2,3-d:5,4-d]dipyrimidine-2,4(3H,9H)-dione, 5-amino-9-.beta.-D-ribofuranosyl- Structure

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

4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine-5-thione Structure

4-amino-9-(β-D-...

~32%

4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4-amino-9-(β-D-...

5,8-diamino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene-7-carbothioamide Structure

5,8-diamino-9-[...

~%

4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4-amino-9-(β-D-...

(Z)-Methanimidic acid Structure

(Z)-Methanimidi...

6-amino-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile Structure

6-amino-7-β-D-r...

~51%

4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4-amino-9-(β-D-...

4-amino-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine-5-thione Structure

4-amino-9-(β-D-...

4-nitrobenzylbromide Structure

4-nitrobenzylbromide

~71%

4-amino-5-<(p-nitrobenzyl)thio>-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4-amino-5-<(p-n...

5,8-diamino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4,9-triazabicyclo[4.3.0]nona-1,3,5,7-tetraene-7-carbothioamide Structure

5,8-diamino-9-[...

~%

4-amino-5-<(p-nitrobenzyl)thio>-9-(β-D-ribofuranosyl)pyrrolo<2,3-d:5,4-d'>dipyrimidine Structure

4-amino-5-<(p-n...