14047-27-9

Basic information

• Product Name: 9H-Purine-9-ethanol, 6-aMino-a-Methyl-, (S)-
• Synonyms: 9H-Purine-9-ethanol, 6-aMino-a-Methyl-, (S)-;L-(+)-9-(2-Hydroxypropyl)adenine;(S)-(-)-9-(2-Hydroxypropyl)adenine;(S)-1-(6-AMino-9H-purin-9-yl)propan-2-ol;Tenofovir Related Compound 9
• CAS NO: 14047-27-9
• Molecular Formula: C₈H₁₁N₅O
• Molecular Weight: 193.20584
• Mol File: 14047-27-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 457.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1.57±0.1 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 14.42±0.20(Predicted)
• CAS DataBase Reference: 9H-Purine-9-ethanol, 6-aMino-a-Methyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 9H-Purine-9-ethanol, 6-aMino-a-Methyl-, (S)-(14047-27-9)
• EPA Substance Registry System: 9H-Purine-9-ethanol, 6-aMino-a-Methyl-, (S)-(14047-27-9)

Safety Data

• Hazardous Substances Data: 14047-27-9(Hazardous Substances Data)

Usage

Uses

(S)-9-[2-(Hydroxypropyl] Adenine is an inhibitor of adenosine deaminase. (S)-9-[2-(Hydroxypropyl] Adenine is used in the preparation of antiviral acyclic nucleoside thiophosphonates such as (S)-Tenofovir Disoproxil Fumarate (T018506).

InChI:InChI=1S/C8H11N5O/c1-5(14)2-13-4-12-6-7(9)10-3-11-8(6)13/h3-5,14H,2H2,1H3,(H2,9,10,11)

Upstream product

• 160707-13-1 (S)-9-<2-(2-tetrahydropyranyloxy)propyl>adenine 
• 66224-66-6 adenine 
• 16606-55-6 (R)-1,2-propylene carbonate 
• 105970-02-3 1-(6-amino-9H-purin-9-yl)propan-2-one 
• 4121-40-8 9-propenyladenine 
• 6034-68-0 N⁶-acetyladenine 

Downstream Products

• 201341-05-1 tenofovir disoproxil 
• 180587-75-1 (R)-diethyl (((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate 
• 147127-19-3 (S)-9-(2-phosphonylmethoxypropyl)adenine 
• 160616-43-3 (S)-9-(2-hydroxypropyl)-N⁶-benzoyladenine 

Relevant articles and documents

A method of synthesis for fuwei intermediates (by machine translation)

The invention discloses a method for synthesizing for fuwei intermediate of the method, the method comprises: formula 2 compound of formula 9 - propenyl adenine as raw materials, in the (S)- (-) - 2, 2 '- double (b benzene phosphine base) - 1, 1' - binaphthyl induction, and tetramethyl piperidine nitrogen oxide oxidation reaction to obtain the type 1 indicated by the tenofovir intermediate (R)- 9 - (2 - hydroxy-propyl) adenine; Through the method of the invention for the preparation of tenofovir intermediate (R)- 9 - (2 - hydroxy-propyl) adenine, mild reaction conditions, the industrial application and popularization; yield of the object product, good selectivity; without using a large amount of chiral compounds, the use of a small amount of chiral auxiliary can be induced oxidation, the cost is low. (by machine translation)

Ester prodrugs of acyclic nucleoside thiophosphonates compared to phosphonates: Synthesis, antiviral activity and decomposition study

9-[2-(Thiophosphonomethoxy)ethyl]adenine [S-PMEA, 8] and (R)-9-[2-(Thiophosphonomethoxy)propyl]adenine [S-PMPA, 9] are acyclic nucleoside thiophosphonates we described recently that display the same antiviral spectrum (DNA viruses) as approved and potent phosphonates PMEA and (R)-PMPA. Here, we describe the synthesis, antiviral activities in infected cell cultures and decomposition study of bis(pivaloyloxymethoxy)-S-PMEA [Bis-POM-S-PMEA, 13] and bis(isopropyloxymethylcarbonyl)-S-PMPA [Bis-POC-S-PMPA, 14] as orally bioavailable prodrugs of the S-PMEA 8 and S-PMPA 9, in comparison to the equivalent "non-thio" derivatives [Bis-POM-PMEA, 11] and [Bis-POC-PMPA, 12]. Compounds 11, 12, 13 and 14 were evaluated for their in vitro antiviral activity against HIV-1-, HIV-2-, HBV- and a broad panel of DNA viruses, and found to exhibit moderate to potent antiviral activity. In order to determine the decomposition pathway of the prodrugs 11, 12, 13 and 14 into parent compounds PMEA, PMPA, 8 and 9, kinetic data and decomposition pathways in several media are presented. As expected, bis-POM-S-PMEA 13 and bis-POC-S-PMPA 14 behaved as prodrugs of S-PMEA 8 and S-PMPA 9. However, thiophosphonates 8 and 9 were released very smoothly in cell extracts, in contrast to the release of PMEA and PMPA from "non-thio" prodrugs 11 and 12.