14047-27-9

Usage

Uses

Used in Pharmaceutical Industry:
9H-Purine-9-ethanol, 6-amino-α-methyl-, (S)is used as an inhibitor of adenosine deaminase for the development of antiviral drugs. Adenosine deaminase is an enzyme that plays a crucial role in the purine salvage pathway, and its inhibition can lead to the suppression of viral replication. 9H-Purine-9-ethanol, 6-amino-a-methyl-, (S)serves as a key intermediate in the synthesis of antiviral acyclic nucleoside thiophosphonates, such as (S)-Tenofovir Disoproxil Fumarate (T018506), which is a potent inhibitor of HIV-1 reverse transcriptase and has been used in the treatment of HIV/AIDS.
Used in Research and Development:
9H-Purine-9-ethanol, 6-amino-α-methyl-, (S)is also utilized in the research and development of new drugs and therapeutic agents. Its unique structure and properties make it a valuable compound for exploring novel mechanisms of action and potential applications in various diseases, including cancer, autoimmune disorders, and neurological conditions. Researchers can use 9H-Purine-9-ethanol, 6-amino-a-methyl-, (S)- as a starting material or a building block for the synthesis of more complex molecules with potential therapeutic benefits.

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

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

Downstream Products

• 160616-43-3 (S)-9-(2-hydroxypropyl)-N⁶-benzoyladenine 
• 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 

Relevant academic research and scientific papers

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)

The synthesis of tenofovir and its analogues via asymmetric transfer hydrogenation

A series of tenofovir analogues with potential antiviral and immunobiologically active compounds were synthesized through an asymmetric transfer hydrogenation reaction from achiral purine derivatives. Up to 97% ee and good to excellent yields were achieved under mild conditions through short reaction steps. The present report suggests an efficient process to acquire tenofovir and its analogues.

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.

SYNTHESIS OF ENANTIOMERIC N-(2-PHOSPHONOMETHOXYPROPYL) DERIVATIVES OF PURINE AND PYRIMIDINE BASES. I. THE STEPWISE APPROACH

The (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases (PMP derivatives) exhibit very high activity against retroviruses.This paper describes the synthesis of enantiomeric 9-(2-phosphonomethoxypropyl)adenines (I and XXVII), 9-(2-phosphonomethoxypropyl)-2,6-diaminopurines (II and XXXI), 9-(2-phosphonomethoxypropyl)guanines (III and XXIX) and 1-(R)-(2-phosphonomethoxypropyl)cytosine (XIX) by alkylation of N-protected N-(2-hydroxypropyl) derivatives of the corresponding bases with bis(2-propyl) p-toluenesulfonyloxymethylphosphonate (X), followed by stepwise N- and O-deprotection of the intermediates.The key intermediates, N-(2-hydropxypropyl) derivatives IX and XXV, were obtained by alkylation of the appropriate heterocyclic base with (R)- or (S)-2-(2-tetrahydropyranyloxy)propyl p-toluenesulfonate (VII or XXIII) ans acid hydrolysis of the resulting N- derivatives VIII and XXII.The chiral synthons were prepared by tosylation of (R)- or (S)-2-(2-tetrahydropyranyloxy)propanol (VI or XXI) available by reduction of enantiomeric alkyl 2-O-tetrahydropyranyllactates V and XXI with sodium bis(2-methoxyethyoxy)aluminum hydride.This approach was used for the synthsis of cytosine, adenine and 2,6-diaminopurine derivatives, while compounds derived from guanine were prepared by hydrolysis of 2-amino-6-chloropurine intermediates.Cytosine derivative IXe was also synthesized by alkylation of 4-methoxy-2-pyrimidone followed by ammonolysis of the intermediate IXf.