A method for the synthesis of racemic and optically active 2‐substituted 9‐(2′,3′‐dihydroxypropyl)‐8‐azahypoxanthines and 8‐azaadenines
- 1 August 1991
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 28 (5) , 1351-1355
- https://doi.org/10.1002/jhet.5570280529
Abstract
Several 9‐(2′,3′‐O‐isopropylidene)‐ and 9‐(2′,3′‐dihydroxypropyl)‐8‐azahypoxanthines and 8‐azaadenines were synthesized by a “one pot” method starting from the acetonide of racemic or (S)‐1‐azido‐2,3‐dihydroxypropane, obtained from D‐mannitol. 9‐(2′,3′‐Dihydroxypropyl)‐8‐azapurines were tested as adenosine deaminase inhibitors.Keywords
This publication has 22 references indexed in Scilit:
- “One pot” synthesis of 2‐substituted 9‐(2′‐hydroxy‐3′‐aminopropyl)‐8‐azahypoxanthines and 8‐azaadenines (5‐substituted 3‐(2′‐hydroxy‐3′‐aminopropyl) 7‐amino and 7‐hydroxy‐3H‐1,2,3‐triazolo[4,5‐d]pyrimidines)Journal of Heterocyclic Chemistry, 1989
- Comparative mutagenicity of 3-azido-1,2-propanediol and sodium azide in various pro- and eu-karyote systemsMutation Research - Fundamental and Molecular Mechanisms of Mutagenesis, 1987
- “One pot” synthesis of 2,9‐disubstituted 8‐azaadenines (3,5‐disubstituted 7‐amino‐3H‐1,2,3‐triazolo[4,5‐d]pyrimidines)Journal of Heterocyclic Chemistry, 1987
- High mutagenic activity of 3-azido-1,2-propanediol (azidoglycerol, AG) in strain D7 of Saccharomyces cerevisiaeMutation Research - Fundamental and Molecular Mechanisms of Mutagenesis, 1987
- A facile “one pot” synthesis of 2,9‐disubstituted 8‐azapurin‐6‐ones (3,5‐disubstituted 7‐hydroxy‐3H‐1,2,3‐triazolo[4,5‐d]pyrimidines)Journal of Heterocyclic Chemistry, 1985
- Alkyl esters of 3-adenin-9-yl-2-hydroxypropanoic acid: a new class of broad-spectrum antiviral agentsJournal of Medicinal Chemistry, 1985
- Tight-binding inhibitors—IV. Inhibition of adenosine deaminases by various inhibitorsBiochemical Pharmacology, 1977
- Enzyme inhibitors. 26. Bridging hydrophobic and hydrophilic regions on adenosine deaminase with some 9-(2-hydroxy-3-alkyl)adeninesJournal of Medicinal Chemistry, 1974
- Enzyme inhibitors. 25. Equation to calculate the unknown Ki from two known values of Ki in an R,S, and RS series. Stereoselectivity of inhibition of adenosine deaminase by (R)-, (S)-, and (RS)-9-(1-hydroxy-2-alkyl and -aralkyl)adeninesJournal of Medicinal Chemistry, 1972
- Enzyme Inhibitors. XVIII. Studies on the Stereoselectivity of Inhibition of Adenosine Deaminase by DL-, D-, and L-9-(2-Hydroxypropyl)adenineJournal of Medicinal Chemistry, 1967