83173-14-2

Basic information

• Product Name: 2-[(4-butylphenyl)amino]-3,7-dihydro-6H-purin-6-one
• CAS NO: 83173-14-2
• Molecular Formula: C₁₅H₁₇N₅O
• Molecular Weight: 283.3284
• Mol File: 83173-14-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 540.5°C at 760 mmHg
• Flash Point: 280.7°C
• Density: 1.35g/cm³
• Vapor Pressure: 9.54E-12mmHg at 25°C
• Refractive Index: 1.692
• CAS DataBase Reference: 2-[(4-butylphenyl)amino]-3,7-dihydro-6H-purin-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(4-butylphenyl)amino]-3,7-dihydro-6H-purin-6-one(83173-14-2)
• EPA Substance Registry System: 2-[(4-butylphenyl)amino]-3,7-dihydro-6H-purin-6-one(83173-14-2)

Safety Data

• Hazardous Substances Data: 83173-14-2(Hazardous Substances Data)

Usage

Class

Purine derivative

Structural relation

Related to adenosine receptors

Pharmaceutical applications

Potential therapeutic agent for neurological and neurodegenerative disorders

Studied disorders

Alzheimer's disease, Parkinson's disease, epilepsy

Mechanism of action

Acts as a selective agonist at the adenosine A3 receptor

Effects

Modulates neurotransmitter release and neuroinflammation

Research status

Promising results in preclinical studies

Future need

Further research to understand pharmacological properties and clinical applications

Upstream product

• 104-13-2 4-Butylaniline 
• 87781-93-9 2-bromo-1,9-dihydro-6H-purin-6-one 

Downstream Products

• 87781-99-5 N²-(p-n-butylphenyl)-9-β-D-ribofuranosylguanine 
• 87782-00-1 2-(4-Butyl-phenylamino)-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,7-dihydro-purin-6-one 
• 87781-95-1 2-(4-Butyl-phenylamino)-7-((2S,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,7-dihydro-purin-6-one 
• 87782-09-0 Imidazole-1-carbothioic acid O-{(2R,3R,3aR,9aR)-2-[2-(4-butyl-phenylamino)-6-oxo-1,6-dihydro-purin-9-yl]-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl} ester 
• 104715-72-2 C₃₆H₃₆ClN₅O₅ 
• 87781-98-4 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-(4-butyl-phenylamino)-6-oxo-1,6-dihydro-purin-7-yl]-tetrahydro-furan-3-yl ester 
• 87782-08-9 2-(4-Butyl-phenylamino)-9-((2R,3R,3aS,9aR)-3-hydroxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1,9-dihydro-purin-6-one 
• 87781-97-3 N²-(4-n-butylphenyl)-2',3',5'-O-triacetylguanosine 
• 87782-01-2 N²-(p-n-butylphenyl)-9-<2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisilox-1,3-diyl)-β-D-ribofuranosyl>guanine 
• 99304-82-2 2-(p-n-butylanilino)-2'-deoxyadenosine 
• 104715-74-4 2-(p-n-butylanilino)-9-(2-deoxy-β-D-ribofuranosyl)purine 
• 104715-70-0 2-(p-n-butylanilino)-6-(methylthio)purine 
• 87781-96-2 N2-(p-n-Butylphenyl)-9-(2-deoxy-β-D-ribofuranosyl)guanine 
• 104715-71-1 2-(p-n-butylanilino)-6-chloro-9-(2-deoxy-3,5-di-p-toluoyl-β-D-ribofuranosyl)purine 

Relevant articles and documents

Synthesis, Cell Growth Inhibition, and Antitumor Screening of 2-(p-n-Butylanilino)purines and Their Nucleoside Analogues

Derivatives of N2-(p-n-butylphenyl)guanine (BuPG) and 2-(p-n-butylanilino)adenine (BuAA) were synthesized and tested as inhibitors of mammalian DNA polymerase α, cell growth, and macromolecule synthesis. 2-(p-n-Butylanilino)-6-chloropurine (BuACl) served as a useful intermediate to prepare a series of 6-substituted analogues.BuACl, as its sodium salt, reacted with 2-deoxy-3,5-di-p-toluoyl-β-D-ribofuranosyl chloride in acetonitrile to give 64percent of the corresponding 9-β nucleoside (blocked BuAdCl) and only 14percent of the 7-β isomer.Deblocking and substitution of chlorine in BuAdCl generated a series of 2-(p-n-butylanilino)-9-(2-deoxy-β-D-ribofuranosyl)purine derivatives.Reaction of the sodium salt of BuACl with (2-acetoxyethoxy)methyl bromide also afforded, after deblocking and substitution of 6-chloro group, a series of 2-(p-n-butylanilino)-9-purines.The bases synthesized were inhibitors of DNA polymerase α isolated from Chinese hamster ovary cells, the most potent compounds being 6-methoxy and 6-methylthio derivatives of 2-(p-n-butylanilino)purine.When tested for their ability to inhibit thymidine incorporation into DNA in HeLa cell cultures and the growth of expotentially growing HeLa cells, 9-(2-deoxy-β-D-ribofuranosyl) derivatives had greater potency than their base counterparts, but "adenine" analogues, such as 2-(p-n-butylanilino)-2'-deoxyadenosine (BuAdA, IC50= 1 μM), were considerably more potent than N2-(p-n-butylphenyl)-2'-deoxyguanosine (BuPdG, IC50= 25 μM).Derivatives bearing the 9- group were nearly as potent inhibitors of thymidine incorporation in these experiments as the corresponding deoxyribonucleotides.Base and deoxynucleoside derivatives also inhibit cellular RNA synthesis, and several compounds, at high concentrations, inhibited protein synthesis.BuPG, BuAA, and four deoxyribonucleoside derivatives of 2-(p-n-butylanilino)purines were tested against P-388 lymphocytic leukemia in mice.None of the compounds increased the survival time of test animals, but two of them, BuAdA and its 6-desamino derivative BuAdP, were lethal at the highest concentration used (400 mg/kg).