716-17-6

Usage

Uses

Used in Biochemistry and Molecular Biology Research:
(2R)-3-(6-aminopurin-9-yl)propane-1,2-diol serves as a research tool in biochemistry and molecular biology, aiding scientists in understanding the mechanisms of nucleic acid function and the role of purines in biological processes.
Used in the Synthesis of Nucleoside Analogs:
(2R)-3-(6-aminopurin-9-yl)propane-1,2-diol is utilized in the synthesis of nucleoside analogs, which are structurally similar to natural nucleosides but differ in specific functional groups. Nucleoside analogs have applications in various fields, including medicine, where they can be used as antiviral or anticancer agents due to their ability to interfere with nucleic acid synthesis and function.

InChI:InChI=1/C8H11N5O2/c9-7-6-8(11-3-10-7)13(4-12-6)1-5(15)2-14/h3-5,14-15H,1-2H2,(H2,9,10,11)

Upstream product

• 69369-04-6 9-(RS)-(2,3-dihydroxypropyl)-8-bromoadenine 
• 94535-30-5 Methyl (RS)-3-(Adenin-9-yl)-2-hydroxypropanoate 
• 76512-99-7 N⁶-formyl-9-(2,3-dihydroxypropyl)adenine 
• 4704-77-2 1-bromo-2,3-propanediol 
• 66224-66-6 adenine 
• 556-52-5 oxiranyl-methanol 
• 23485-30-5 N⁹-(2,2-diethoxyethyl)adenine 
• 33841-98-4 2-(6-amino-9H-purin-9-yl)acetaldehyde 
• 94535-32-7 (RS)-3-(Adenin-9-yl)-2-hydroxypropanoic Acid 

Downstream Products

• 81546-79-4 9-((RS)-3-p-toluenesulfonyloxy-2-(tetrahydropyran-2-yloxy)propyl)adenine 
• 69369-04-6 9-(RS)-(2,3-dihydroxypropyl)-8-bromoadenine 
• 70259-40-4 9-((RS)-2,3-bis-p-toluenesulfonyloxypropyl)adenine 
• 81546-78-3 9-((RS)-3-p-toluenesulfonyloxy-2-hydroxypropyl)adenine 
• 121552-02-1 1-[6-(Trityl-amino)-purin-9-yl]-3-trityloxy-propan-2-ol 
• 87888-92-4 C₂₂H₂₃N₅O₇S₂ 
• 87888-91-3 Toluene-4-sulfonic acid 3-(6-amino-8-hydroxy-purin-9-yl)-2-hydroxy-propyl ester 
• 123156-39-8 [2-(6-Benzoylamino-purin-9-yl)-1-hydroxy-ethyl]-phosphonic acid diethyl ester 
• 87888-88-8 8-Benzyloxy-9-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-9H-purin-6-ylamine 

Relevant academic research and scientific papers

Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family

Adenine derivatives bearing substituents in the 2-, N6-, 7-, 8-, and/or 9-position and a series of deazapurines were synthesized and investigated in [3H]adenine binding studies at the adenine receptor in rat brain cortical membrane preparations (rAde1R). Steep structure-activity relationships were observed. Substitution in the 8-position (amino, dimethylamino, piperidinyl, piperazinyl) or in the 9-position (2-morpholinoethyl) with basic residues or introduction of polar substituents at the 6-amino function (hydroxy, amino, acetyl) represented the best modifications. Functional evaluation of selected adenine derivatives in adenylate cyclase assays at 1321N1 astrocytoma cells stably expressing the rAde1R showed that all compounds investigated were agonists or partial agonists. A subset of compounds was additionally investigated in binding studies at human embryonic kidney (HEK293) cells, which also express a high-affinity adenine binding site. Structure-affinity relationships at the human cell line were similar to those at the rAde1R, but not identical. In particular, N 6-acetyladenine (25, Ki rat: 2.85 μM; Ki human: 0.515 μM) and 8-aminoadenine (33, Ki rat: 6.51 μM; Ki human: 0.0341 μM) were much more potent at the human as compared to the rat binding site. The new AdeR ligands may serve as lead structures and contribute to the elucidation of the functions of the adenine receptor family. 2009 American Chemical Society.

8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands

Importance of making available selective adenosine receptor antagonists is boosted by recent findings of adenosine involvement in many CNS dysfunctions. In the present work a series of 8-bromo-9-alkyl adenines are prepared and fully characterized in radio

Reaction of 8-Substituted Adenines with Glycidol

The regioselectivity of isomer formation in the reaction of 8-substituted adenines with glycidol depends on steric factors of substituents.The compounds prepared were tested for immunostimulating activity.

Dioxolane nucleosides and their phosphonate derivatives: synthesis and hydrolytic stability

Several new nucleoside (12-15) and nucleoside phosphonate (27-30) analogues derived from (+/-)-cis- and -trans-2-hydroxymethyl-4-methyl-1,3-dioxolane have been prepared and their configurations assigned by 1H NMR spectroscopy.First-order rate constants fo

EASY ALKYLATION OF PURINE BASES BY SOLID-LIQUID PHASE TRANSFER CATALYSIS WITHOUT SOLVENT. STRUCTURAL ANALYSIS BY 2D HETERONUCLEAR 1H 13C CORRELATED NMR SPECTROSCOPY

Solid-liquid PTC without added organic solvent promotes alkylation of purine derivatives leading in particular to an efficient synthesis of the antiviral DHPA.The location of the substituent on the ring was determined by analysis of coupling interactions

PREPARATION AND SYNTHETIC UTILIZATION OF 3-(ADENIN-9-YL)-2-HYDROXYALKANOIC ACIDS AND THEIR DERIVATIVES

Condensation of adenine and its substituted derivatives with 1,1-dialkoxy-2-bromoalkanes afforded substituted 2-(adenin-9-yl)-1,1-dialkoxyalkanes I and IV.Acid hydrolysis of I or IV, followed by reaction with alkali metal cyanides and acid hydrolysis, gave substituted 3-(adenin-9-yl)-2-hydroxyalkanoic acids II, V and VI.Methyl esters of these compounds (VIII) were converted into 3-(adenin-9-yl)alkane-1,2-diols IX by reduction with sodium borohydride. 3-(Adenin-9-yl)-2-methoxypropanoic acid (XVII) was obtained by oxidation of 9-(3-hydroxy-2-methoxypropyl)adenine (XVI)with sodium periodate; 4-(adenin-9-yl)-2-(S)-hydroxybutanoic acid (XXVII) was synthesized by oxidation of 9-(S)-(2-tetrahydropyranyloxy-4-hydroxybutyl)adenine (XXV), prepared from diethyl L-malate.Acid hydrolysis of XXV afforded 9-(S)-(2,4-dihydroxybutyl)adenine (XXVI). 4-(Adenin-9-yl)-3-hydroxypentanoic acid (XXIX) was obtained by reaction of malonic acid with 2-(adenin-9-yl)-1,1-diethoxypropane (IVa) in water.

PREPARATION OF ISOMERIC 3-AMINOPROPYLAMINO DERIVATIVES OF 9-(RS)-(2,3-DIHYDROXYPROPYL)ADENINE

Treatment of 9-(RS)-(2,3-dihydroxypropyl)adenine (III) with bromine in water afforded the 8-bromo derivative IV which on reaction with acetone was converted into the 1,3-dioxolane derivative VI.Reaction of compound VI with 1,3-diaminopropane, followed by acid hydrolysis, gave 9-(R,S)-(2,3-dihydroxypropyl)-8-(3-aminopropylamino)adenine (VIII).Compound IV reacts with 1,3-diaminopropane under formation of a mixture of compound VIII and isomeric 9-(RS)--8-hydroxyadenines (IX,X). 9-(R,S)-(2,3-Dihydroxypropyl)-8-hydroxyadenine (XVII) was prepared by reaction of compound VI with sodium benzoxide in dimethylformamide and subsequent acid hydrolysis.Its tosylation, followed by reaction of the obtained 3'-O-p-toluenesulfonyl derivative XVIII with 1,3-diaminopropane, furnished also the compound IX.In an analogous way, 9-(RS)-adenine (XXI) was prepared from the 3'-O-p-toluenesulfonyl derivative of compound III (XX).

Purines, Pyrimidines, and Imidazoles. Part 56. Some Aminoimidazolecarboxamidines and Derived Adenines

5-Amino-4-cyano-1-cyclohexylimidazole, prepared from aminomalononitrile, triethyl orthoformate, and cyclohexylamine with methanolic hydrogen chloride, produced methyl 5-amino-1-cyclohexylimidazole-4-carboximidate, which with ammonia gave 5-amino-1-cyclohe