22415-88-9

Basic information

• Product Name: Homoadenosine
• Synonyms: Homoadenosine;9-(5-Deoxy-beta-D-ribo-hexofuranosyl)-9H-purin-6-amine;NSC 82223;2-(6-aminopurin-9-yl)-5-(2-hydroxyethyl)oxolane-3,4-diol
• CAS NO: 22415-88-9
• Molecular Formula: C₁₁H₁₅N₅O₄
• Molecular Weight: 281.2679
• Mol File: 22415-88-9.mol

Chemical Properties

• Boiling Point: 664.2°Cat760mmHg
• Flash Point: 355.5°C
• Appearance: /
• Density: 1.94g/cm³
• Vapor Pressure: 1.51E-18mmHg at 25°C
• Refractive Index: 1.852
• CAS DataBase Reference: Homoadenosine(CAS DataBase Reference)
• NIST Chemistry Reference: Homoadenosine(22415-88-9)
• EPA Substance Registry System: Homoadenosine(22415-88-9)

Safety Data

• Hazardous Substances Data: 22415-88-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
Homoadenosine is used as a building block for the synthesis of nucleoside analogs, contributing to the development of novel therapeutic agents.
Used in Central Nervous System Applications:
Homoadenosine is used as a neuroprotective agent for its potential to shield the nervous system from damage, offering benefits in treating neurological disorders.
Used in Cardiovascular System Applications:
In the cardiovascular system, homoadenosine is used to modulate physiological processes, potentially contributing to the treatment of heart-related conditions.
Used in Immune System Applications:
Homoadenosine is utilized for its anti-inflammatory properties, supporting immune system regulation and potentially aiding in the management of inflammatory diseases.
Used as an Agonist of the Adenosine A3 Receptor:
Homoadenosine is used as a potent agonist of the adenosine A3 receptor, which may enhance its therapeutic effects in various physiological and pathological conditions.

InChI:InChI=1/C11H15N5O4/c12-9-6-10(14-3-13-9)16(4-15-6)11-8(19)7(18)5(20-11)1-2-17/h3-5,7-8,11,17-19H,1-2H2,(H2,12,13,14)

Upstream product

• 55085-28-4 5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 66224-66-6 adenine 
• 5605-63-0 ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate 
• 4005-49-6 N-benzoyladenine 
• 113808-24-5 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-trityl-α-D-ribo-hexofuranose 
• 124572-47-0 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-trityl-α-D-xylo-hexofuranose 
• 113808-23-4 5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-ribo-hexofuranose 
• 37070-23-8 5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-xylohexofuranose 
• 124572-45-8 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 113808-25-6 3-O-benzoyloxy-5-deoxy-1,2-O-isopropylidene-α-D-ribohexofuranose 
• 124572-46-9 6-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 124572-48-1 6-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 124572-44-7 (5E)-3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-trityl-α-D-xylo-hexofuran-5-enose 
• 88270-97-7 1,2-di-O-acetyl-3,6-di-O-benzoyl-5-deoxy-D-ribo-hexofuranose 

Relevant articles and documents

S-homoadenosyl-L-cysteine and S-homoadenosyl-L-homocysteine. Synthesis and binding studies of non-hydrolyzed substrate analogues with S-adenosyl-L-homocysteine hydrolase

Treatment of homoadenosine [9-(5-deoxy-β-D-ribo-hexofuranosyl)adenine] with thionyl chloride and pyridine in acetonitrile gave 6′-chloro-6′-deoxyhomoadenosine, which underwent nucleophilic displacement with L-cysteine or L-homocysteine to give homologated analogues of S-adenosyl-L-homocysteine. Each amino acid in aqueous sodium hydroxide at 60 °C gave excellent conversion from the chloronucleoside, and adsorption on Amberlite XAD-4 resin provided more convenient isolation than prior methods. Weak binding of these non-hydrolyzed analogues to S-adenosyl-L-homocysteine hydrolase was observed.

5′-Homoaristeromycin. Synthesis and antiviral activity against orthopox viruses

An efficient synthesis of 5′-homoaristeromycin has been developed. This permitted an extensive antiviral analysis, which found potent activity toward vaccinia, cowpox, and monkeypox viruses. For comparative purposes, 5′-homoadenosine was made available by a newly designed route and found to be inactive.

Biomimetic simulation of free radical-initiated cascade reactions postulated to occur at the active site of ribonucleotide reductases

Treatment of 5'-O-nitro esters of nucleosides with tributylstannane and AIBN at elevated temperatures caused β-scission of the resulting 5'-oxygen radical to give formaldehyde and dehomologated erythrofuranosyl nucleosides. Analogous treatment of 6'-O-nitro esters of homonucleosides [(5-deoxy-β-D- ribo-hexofuranosyl)adenine or uracil nucleosides derived from D-glucose] resulted in generation of a 6'-oxygen radical followed by abstraction of H3' by a [1,5]-hydrogen shift. Radical quenching with tributyltin deuteride gave 3'-[2H]homonucleosides. This deuterium transfer, and inversion of configuration at C3' with unprotected homonucleosides, confirmed the relay- generation of C3' free radicals. Analogous treatment of 6'-O-nitro esters of homonucleosides containing a 2'-chloro (30) or 2'-O-tosyl (40) substituent resulted in complete disappearance of starting material and generation of (R)-2-(2-hydroxyethyl)-3(2H)-furanone (33). Generation of a 6'-oxygen radical, [1,5]-hydrogen shift of H3' to give a C3' radical, and loss of the 2'-substituent would give unstable intermediates that could lose the heterocyclic base from Cl' to give 33. This radical-initiated cascade simulates reactions postulated to occur at the active site of ribonucleotide reductases. Generation of a C3' radical from 40 and loss of toluenesulfonic acid via a [1,2]-electron shift would generate a radical intermediate that could undergo deuterium transfer followed by β-elimination of the base to give the deuterated furanone 33 as observed. This is in harmony with a new mechanism for substrate reduction of nucleotides to give 2'-deoxy products. Generation of a C3' radical from 30 and loss of a chlorine atom by β- radical elimination would result in conjugate elimination of base and generation of 33 without incorporation of deuterium, as observed. Thus, one- electron elimination processes (as well as the previously postulated two- electron loss with groups from C2') must be considered with mechanism-based inactivators of ribonucleotide reductases. Biomimetic reactions and new mechanistic considerations are discussed.

USE OF 5-DEOXY-ribo-HEXOFURANOSE DERIVATIVES FOR THE PREPARATION OF 5'-NUCLEOTIDE PHOSPHONATES AND HOMORIBONUCLEOSIDES

A convenient and general method is proposed for the synthesis of 5'-nucleotide phosphonate analogs starting from 5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose which can easily be produced in preparative quantities from D-glucose.Phosphonate IIIa was synthesized by means of the Arbuzov reaction between 3-O-benzoyl-6-bromo-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose and triethyl phosphite.The consecutive acetolysis, condensation with uracil and N6-benzoyladenine bis-trimethylsilyl derivatives and deblocking possessed phosphonate analogs of 5'-nucleotides in good yields.The intermediate 5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose derivatives were used for the preparation of homonucleosides.

Synthesis and Conformational Analysis of Some 5'-Homoadenosine Derivatives

The syntheses of the homoadenosines 9-(5-deoxy-β-D-ribo-hexofuranosyl)adenine (2) and 9-(5,6-dideoxy-β-ribo-heptofuranosyl)adenine (3) as well as the 5'-homo-AMP analogue 9-(5,6-dideoxy-6-phosphono-β-D-ribo-hexofuranosyl)adenine (4) are described.The conf