13146-72-0

Usage

Uses

Used in Pharmaceutical Industry:
3'-Deoxyinosine is used as an Inosine analog for its potential use as an antileishmanial drug, targeting Leishmania parasites and inhibiting their growth.
Used in Research Applications:
3'-Deoxyinosine is used as an inhibiting agent in studies of Trypanosoma cruzi growth inside host cells in vitro, providing valuable insights into the development of treatments for Chagas disease.
Used as an Impurity in Antiviral Drug Production:
3'-Deoxyinosine is an impurity of the antiviral drug 2',3'-Dideoxyinosine (D440950), which is used to treat HIV/AIDS and hepatitis B virus infections. Its presence in the production process may affect the drug's efficacy and safety, making it important to monitor and control its levels.

Upstream product

• 125790-82-1 9-(2',5'-di-O-acetyl-3'-bromo-3'-deoxy-β-D-xylofuranosyl)hypoxanthine 
• 73-03-0 cordycepin 
• 1445-45-0 Trimethyl orthoacetate 
• 506-96-7 Acetyl bromide 
• 58-63-9 inosine 
• 58-63-9 Inosine 
• 2627-64-7 9-(2,3-anhydro-β-D-ribofuranosyl)adenine 
• 58-61-7 adenosine 
• 204978-87-0 2',5'-di-O-acetyl-3'-deoxyinosine 
• 125790-82-1 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)-1,9-dihydro-6H-purine-6-one 
• 65870-99-7 2',3'-O-(1-methoxyethylidene)inosine 

Downstream Products

• 204978-87-0 2',5'-di-O-acetyl-3'-deoxyinosine 
• 68-94-0 hypoxanthine 
• 115044-75-2 (2R,3R,5S)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol 
• 15386-69-3 (2R,3R,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol 
• 58-63-9 Inosine 
• 7084-29-9 3'-deoxy-5-methyluridine 
• 68-94-0 Allopurinol 
• 56220-55-4 5-amino-1-(3-deoxy-β-D-ribofuranosyl)imidazole-4-carboxamide 

Relevant academic research and scientific papers

The action of adenosine deaminase (E.C. 3.5.4.4.) on adenosine and deoxyadenosine acetates: The crucial role of the 5'-hydroxy group for the enzyme activity

From adenosine 1, 2'-deoxyadenosine 3 and 3'-deoxyadenosine 5 all the acetates were prepared by lipase-catalyzed reactions. Only the acetates with free 5'-hydroxy group were deaminated by adenosine deaminase (ADA), confirming the crucial role of 5'-OH for the enzyme activity. (C) 2000 Elsevier Science Ltd.

Deamination of 6-aminodeoxyfutalosine in menaquinone biosynthesis by distantly related enzymes

Proteins of unknown function belonging to cog1816 and cog0402 were characterized. Sav2595 from Steptomyces avermitilis MA-4680, Acel0264 from Acidothermus cellulolyticus 11B, Nis0429 from Nitratiruptor sp. SB155-2 and Dr0824 from Deinococcus radiodurans R1 were cloned, purified, and their substrate profiles determined. These enzymes were previously incorrectly annotated as adenosine deaminases or chlorohydrolases. It was shown here that these enzymes actually deaminate 6-aminodeoxyfutalosine. The deamination of 6-aminodeoxyfutalosine is part of an alternative menaquinone biosynthetic pathway that involves the formation of futalosine. 6-Aminodeoxyfutalosine is deaminated by these enzymes with catalytic efficiencies greater than 10 5 M-1 s-1, Km values of 0.9-6.0 μM, and kcat values of 1.2-8.6 s-1. Adenosine, 2′-deoxyadenosine, thiomethyladenosine, and S-adenosylhomocysteine are deaminated at least an order of magnitude slower than 6-aminodeoxyfutalosine. The crystal structure of Nis0429 was determined and the substrate, 6-aminodeoxyfutalosine, was positioned in the active site on the basis of the presence of adventitiously bound benzoic acid. In this model, Ser-145 interacts with the carboxylate moiety of the substrate. The structure of Dr0824 was also determined, but a collapsed active site pocket prevented docking of substrates. A computational model of Sav2595 was built on the basis of the crystal structure of adenosine deaminase and substrates were docked. The model predicted a conserved arginine after β-strand 1 to be partially responsible for the substrate specificity of Sav2595.

APPLICATION OF 3'-DEOXYINOSINE IN PREPARATION OF DRUG, FOOD OR HEALTH PRODUCT FOR MULTIPLE DISEASE

The present invention relates to the field of drug, provides an application of 3'-deoxyinosine in the preparation of food, drug or health products for the prevention or treatment of diet-induced obesity or hyperlipidemia, provides an application of 3'-deoxyinosine in the preparation of food, drug or health products for the prevention of hypertension or arteriosclerosis, and further provides an application of 3'-deoxyinosine in the preparation of skin care products. Studies of the present invention have indicated that 3'-deoxyinosine plays a significant role in treating hyperlipidemia and reducing weights of patients with diet-induced obesity, overcoming the existing technical prejudice. Moreover, 3'-deoxyinosine has a more extensive effect on preventing or treating hyperlipidemia compared with the existing medications. Meanwhile, 3'-deoxyinosine is able to effectively prevent the development of hypertension and arteriosclerosis by reducing serum lipid content and high-density lipoprotein (HDL) content.

C6–O-alkylated 7-deazainosine nucleoside analogues: Discovery of potent and selective anti-sleeping sickness agents

African trypanosomiasis, a deadly infectious disease caused by the protozoan Trypanosoma brucei spp., is spread to new hosts by bites of infected tsetse flies. Currently approved therapies all have their specific drawbacks, prompting a search for novel th

The Chemoenzymatic Synthesis of 2-Chloro- and 2-Fluorocordycepins

Two approaches to the chemoenzymatic synthesis of 2-fluorocordycepin and 2-chlorocordycepin were studied: (i) the use of 3′-deoxyadenosine (cordycepin) and 3′-deoxyinosine (3′dIno) as donors of 3-deoxy- d -ribofuranose in the transglycosylation of 2-fluoro- (2F Ade) and 2-chloroadenine (2Cl Ade) catalyzed by the recombinant E. coli purine nucleoside phosphorylase (PNP), and (ii) the use of 2-fluoroadenosine and 3′-deoxyinosine as substrates of the cross-glycosylation and PNP as a biocatalyst. An efficient method for 3′-deoxyinosine synthesis starting from inosine was developed. However, the very poor solubility of 2Cl Ade and 2F Ade is the limiting factor of the first approach. The second approach enables this problem to be overcome and it appears to be advantageous over the former approach from the viewpoint of practical synthesis of the title nucleosides. The 3-deoxy-α- d -ribofuranose-1-phosphate intermediary formed in the 3′dIno phosphorolysis by PNP was found to be the weak and marginal substrate of E. coli thymidine (TP) and uridine (UP) phosphorylases, respectively. Finally, one-pot cascade transformation of 3-deoxy- d -ribose in cordycepin in the presence of adenine and E. coli ribokinase, phosphopentomutase, and PNP was tested and cordycepin formation in ca. 3.4% yield was proved.

Structure-activity relationships of synthetic cordycepin analogues as experimental therapeutics for African trypanosomiasis

Novel methods for treatment of African trypanosomiasis, caused by infection with Trypanosoma brucei are needed. Cordycepin (3′-deoxyadenosine, 1a) is a powerful trypanocidal compound in vitro but is ineffective in vivo because of rapid metabolic degradation by adenosine deaminase (ADA). We elucidated the structural moieties of cordycepin required for trypanocidal activity and designed analogues that retained trypanotoxicity while gaining resistance to ADA-mediated metabolism. 2-Fluorocordycepin (2-fluoro-3′-deoxyadenosine, 1b) was identified as a selective, potent, and ADA-resistant trypanocidal compound that cured T. brucei infection in mice. Compound 1b is transported through the high affinity TbAT1/P2 adenosine transporter and is a substrate of T. b. brucei adenosine kinase. 1b has good preclinical properties suitable for an oral drug, albeit a relatively short plasma half-life. We present a rapid and efficient synthesis of 2-halogenated cordycepins, also useful synthons for the development of additional novel C2-substituted 3′-deoxyadenosine analogues to be evaluated in development of experimental therapeutics.

Synthesis of 2-alkynylcordycepins and evaluation of their vasodilating activity

Based on the recently developed lithiation-mediated stannyl migration of 6-chloropurine derivatives, 2-iodocordycepin was prepared from cordycepin. The reaction of this compound with terminal alkynes was carried out to synthesize a series of 2-alkynyl der

Synthesis of 2′,3′-dideoxypurinenucleosides via the palladium catalyzed reduction of 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)purine derivatives

Practical method to produce 2′,3′-dideoxypurinenucleosides from 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)purines (1) was developed. High ratio of 2′,3′-dideoxynucleoside to 3′-deoxyribonucleoside was obtained by selecting the reaction conditions (solvent, pH and/or base), or changing 2′-acyloxy leaving group. The reaction mechanism was studied by deuteration experiments of 1a and 1-(3,5-di-O-acetyl-2-bromo-2-deoxy-β-D-ribofuranosyl)thymine (12).

Process for preparing 2',3'-dideoxyadenosine

A process for preparing 2',3'-dideoxyadenosine of the formula STR1 wherein B is adenine, wherein R1 is hydrogen, C1-12 acyl, C1-12 alkyl, C7-8 aralkyl, or silyl, said process comprising: reducing a nucleoside of the formula IIIa or IIIb STR2 wherein R2 is hydrogen, C1-12 acyl, C1-12 alkyl, C7-8 aralkyl or silyl; X is Cl, Br or I; R5 is C1-12 acyl and B is adenine, with hydrogen in the presence of a palladium catalyst and aqueous solvent mixture of acetonitrile or ethyl acetate and water, said aqueous solvent containing a base selected from the group consisting of sodium hydroxide/sodium acetate and sodium carbonate/sodium acetate, wherein said solvent has a pH of 9-11.