15763-12-9

Basic information

• Product Name: N-allyladenosine
• Synonyms: N-allyladenosine
• CAS NO: 15763-12-9
• Molecular Formula: C13H17N5O4
• Molecular Weight: 307.31
• Mol File: 15763-12-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 165-167 °C
• Boiling Point: 646.2°Cat760mmHg
• Flash Point: 344.6°C
• Appearance: /
• Density: 1.67g/cm³
• Vapor Pressure: 1.4E-17mmHg at 25°C
• Refractive Index: 1.749
• PKA: 13.12±0.70(Predicted)
• CAS DataBase Reference: N-allyladenosine(CAS DataBase Reference)
• NIST Chemistry Reference: N-allyladenosine(15763-12-9)
• EPA Substance Registry System: N-allyladenosine(15763-12-9)

Safety Data

• Hazardous Substances Data: 15763-12-9(Hazardous Substances Data)

Usage

Uses

N-Allyladenosine is a new potential anti-?angiogenic compound that targets human microvascular endothelial cells in vitro.

InChI:InChI=1/C13H17N5O4/c1-2-3-14-11-8-12(16-5-15-11)18(6-17-8)13-10(21)9(20)7(4-19)22-13/h2,5-7,9-10,13,19-21H,1,3-4H2,(H,14,15,16)

Upstream product

• 7387-58-8 6-N-2',3',5'-tri-O-tetraacetyladenosine 
• 5987-73-5 2',3',5'-O-triacetyl-6-chloroinosine 
• 3181-38-2 2',3',5'-tri-O-acetylinosine 
• 58-63-9 Inosine 
• 1055040-20-4 6-N-allyl-2',3',5'-tris-O-(tert-butyldimethylsilyl)-6-N-(2-trimethylsilylethoxycarbonyl)adenosine 
• 2004-06-0 6-Chloropurine riboside 
• 107-11-9 1-amino-2-propene 
• 1001067-26-0 2',3',5'-tris-O-(tert-butyldimethylsilyl)-6-N-(2-trimethylsilylethoxycarbonyl)adenosine 

Downstream Products

• 5446-37-7 N⁶-allyladenine 

Relevant articles and documents

Some short-chain N6-substituted adenosine analogues with antitumor properties.

The compounds N6-allyl-, N6-isopropyl-, N6-propargyl-, and N6-(2-methylallyl)adenosine were prepared by reacting 6-chloropurine riboside with an excess of the corresponding amines in ethanol, in the presence of two acid acceptors resulting in virtually quantitative yields. The compounds showed biological activity in a number of in vitro and in vivo tumor cell systems. Very good increases in life spans of mice bearing mammary carcinoma were obtained by treatment with the N6-allyl, N6-isopropyl, and N6-propargyl analogues, respectively. In rats, the N6-allyl analogue slowed the rate of transplantable mammary tumor growth by one-fourth. The short-chain adenosine analogues are more active in the treatment of animal carcinomas than in the leukemia or sarcoma tumor cell systems.

N6-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity

A series of adenosine analogues differently substituted in N 6-position were synthesized to continue our studies on the relationships between structure and biological activity of iPA. The structures of the compounds were confirmed by standard studies of 1H NMR, MS and elemental analysis. These molecules were then evaluated for their anti-proliferative activity on bladder cancer cells. We found that some of these compounds possess anti-proliferative activity but have no effect on cell invasion and metalloprotease activity.

Chemical modification of the plant isoprenoid cytokinin N6-isopentenyladenosine yields a selective inhibitor of human enterovirus 71 replication

In this study, we demonstrate that N6-isopentenyladenosine, which essentially is a plant cytokinin-like compound, exerts a potent and selective antiviral effect on the replication of human enterovirus 71 with an EC50 of 1.0 ± 0.2 mM and a selectivity index (SI) of 5.7. The synthesis of analogs with modification of the N6-position did not result in a lower EC50 value. However, in particular with the synthesis of N6-(5-hexene-2-yne-1-yl)adenosine (EC50 = 4.3 ± 1.5 mM), the selectivity index was significantly increased: because of a reduction in the adverse effect of this compound on the host cells, an SI 101 could be calculated. With this study, we for the first time provide proof that a compound class that is based on the plant cytokinin skeleton offers an interesting starting point for the development of novel antivirals against mammalian viruses, in the present context in particular against enterovirus 71.