Synthesis of 8-Amino- and N-Substituted 8-Aminoadenine Derivatives of Acyclic Nucleoside and Nucleotide Analogs
- 1 January 2001
- journal article
- Published by Institute of Organic Chemistry & Biochemistry in Collection of Czechoslovak Chemical Communications
- Vol. 66 (3) , 517-532
Abstract
8-Aminoadenine derivatives2were obtained from 8-bromoadenines1in one-pot reactionvia8-azidoadenines. Reaction of 8-bromoadenines1with methylamine or dimethylamine in ethanol afforded the correspondingN9-substituted 8-(methylamino)adenines3and 8-(dimethylamino)adenines4. Alkylation of 8-aminoadenine (2a) with diverse alkylation agents affordedN9-substituted 8-aminoadenine derivatives2, and alkylation of 8-(dimethylamino)adenine (4a) gave mixtures of the correspondingN9-substituted 8-(dimethylamino)adenines4and theirN3-substituted regioisomers5. 8,3'-N-Anhydro derivatives7were prepared by tosylation of (S)-8-bromo-9-{2-[(diisopropoxyphosphoryl)- methoxy]-3-hydroxypropyl}adenine (1c) followed by treatment with methanolic ammonia or methylamine solution.Keywords
This publication has 25 references indexed in Scilit:
- Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purin-8(9H)-oneCollection of Czechoslovak Chemical Communications, 2000
- Structure−Antiviral Activity Relationship in the Series of Pyrimidine and Purine N-[2-(2-Phosphonomethoxy)ethyl] Nucleotide Analogues. 1. Derivatives Substituted at the Carbon Atoms of the BaseJournal of Medicinal Chemistry, 1999
- Towards an Effective Chemotherapy of Virus Infections: Therapeutic Potential of Cidofovir [(S)-1-[3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine, HPMPC] for the Treatment of DNA Virus InfectionsCollection of Czechoslovak Chemical Communications, 1998
- Acyclic Nucleotide Analogues and Related CompoundsNucleosides, Nucleotides & Nucleic Acids, 1995
- Syntheses of Enantiomeric N-(3-Hydroxy-2-phosphonomethoxypropyl) Derivatives of Purine and Pyrimidine BasesCollection of Czechoslovak Chemical Communications, 1993
- Phosphonylmethyl Ethers of Nucleosides and Their Acyclic Analogues1989
- Marked in vivo antiretrovirus activity of 9-(2-phosphonylmethoxyethyl)adenine, a selective anti-human immunodeficiency virus agent.Proceedings of the National Academy of Sciences, 1989
- Antiviral activity of phosphonylmethoxyalkyl derivatives of purine and pyrimidinesAntiviral Research, 1987
- Marine toxinsAccounts of Chemical Research, 1977
- Specificity of purine nucleoside phosphorylase from Escherichia coliCollection of Czechoslovak Chemical Communications, 1977