Introduction：Basic information about CAS 4294-16-0|N-Benzyladenosine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | N-Benzyladenosine |
|---|
| CAS Number | 4294-16-0 | Molecular Weight | 357.364 |
|---|
| Density | 1.6±0.1 g/cm3 | Boiling Point | 689.3±65.0 °C at 760 mmHg |
|---|
| Molecular Formula | C17H19N5O4 | Melting Point | 184-186 °C |
|---|
| MSDS | / | Flash Point | 370.7±34.3 °C |
|---|
Names
| Name | n6-benzyladenosine |
|---|
| Synonym | More Synonyms |
|---|
N-Benzyladenosine BiologicalActivity
| Description | N6-Benzyladenosine is an adenosine receptor agonist, has a cytoactive activity. N6-Benzyladenosine arrests cell cycle at G0/G1 phase and induces cell apoptosis. N6-Benzyladenosine also exerts inhibitory effect on T. gondii adenosine kinase and glioma[1]-[5]. |
|---|
| Related Catalog | Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerResearch Areas >>Inflammation/ImmunologySignaling Pathways >>GPCR/G Protein >>Adenosine Receptor |
|---|
| In Vitro | N6-benzyladenosine suppresses the clonogenic activity and the growth of different neoplastic cells[2]. N6-benzyladenosine results cell morphology alteration and actin cytoskeleton disorganization in T24 cell[2]. N6-benzyladenosine (10 μM; 24 h) is a potent inductor of apoptosis, and belongs to apoptotic systems with distinct caspase-3 and caspase-9 activation[3]. N6-benzyladenosine (0-100 μM; 24 h) induces chromatin condensation, formation of apoptotic bodies, and cleavage of DNA to nucleosomal fragments in a dose-dependent manner[3]. N6-benzyladenosine acts as a selective anti-toxoplasma agent with binding affinity to T. gondii adenosine kinase (apparent Km =179.8 μM), over human adenosine kinase[4]. N6-benzyladenosine (0-50 μM) shows weak inhibition against adenosine kinase deficient (TgAKS3) strains of Toxoplasma gondii[4]. N6-benzyladenosine (compound 2) (0.3-20 μM) exerts anti-glioma activity by interfering with the mevalonate pathway and inhibiting FPPS (Farnesyl pyrophosphate synthase) [5]. Apoptosis Analysis[3] Cell Line: HL-60 Concentration: 10 μM Incubation Time: 24 hours Result: Induced cell apoptosis by increasing caspase-3 (DEVDase) as well as caspase-9 (LEHDase) activity, indicating an apoptotic systems with distinct caspase-3/9 activation. Apoptosis Analysis[5] Cell Line: U87MG human glioma cell line. Concentration: 0.3, 0.6, 1.2, 2.5, 5, 10, 20 μM Incubation Time: 48 hours Result: Inhibited glioma growth by interfering with the mevalonate pathway and inhibiting FPPS. |
|---|
| References | [1]. Kaminek M, et al. Cytokinin activities of N6-benzyladenosine derivatives hydroxylated on the side-chain phenyl ring. Journal of Plant Growth Regulation. 1987. 6(2):113. [2]. Castiglioni S, et al. N6-isopentenyladenosine and its analogue N6-benzyladenosine induce cell cycle arrest and apoptosis in bladder carcinoma T24 cells. Anticancer Agents Med Chem. 2013 May;13(4):672-8. [3]. Mlejnek P. Caspase inhibition and N6-benzyladenosine-induced apoptosis in HL-60 cells. J Cell Biochem. 2001;83(4):678-89. [4]. Kim YA, et al. Synthesis, biological evaluation and molecular modeling studies of N6-benzyladenosine analogues as potential anti-toxoplasma agents. Biochem Pharmacol. 2007 May 15;73(10):1558-72. [5]. Grimaldi M, et al. NMR for screening and a biochemical assay: Identification of new FPPS inhibitors exerting anticancer activity. Bioorg Chem. 2020 May;98:103449. |
|---|
Chemical & Physical Properties
| Density | 1.6±0.1 g/cm3 |
|---|
| Boiling Point | 689.3±65.0 °C at 760 mmHg |
|---|
| Melting Point | 184-186 °C |
|---|
| Molecular Formula | C17H19N5O4 |
|---|
| Molecular Weight | 357.364 |
|---|
| Flash Point | 370.7±34.3 °C |
|---|
| Exact Mass | 357.143707 |
|---|
| PSA | 125.55000 |
|---|
| LogP | 1.04 |
|---|
| Vapour Pressure | 0.0±2.3 mmHg at 25°C |
|---|
| Index of Refraction | 1.763 |
|---|
| InChIKey | MRPKNNSABYPGBF-LSCFUAHRSA-N |
|---|
| SMILES | OCC1OC(n2cnc3c(NCc4ccccc4)ncnc32)C(O)C1O |
|---|
| Storage condition | 2-8°C |
|---|
Safety Information
| Hazard Codes | Xn |
|---|
| Risk Phrases | 20/21/22-36/37/38 |
|---|
| Safety Phrases | S22-S24/25 |
|---|
| WGK Germany | 3 |
|---|
Synonyms
| Adenosine, N-(phenylmethyl)- |
| Adenosine, N-benzyl- |
| BAP RIBOSE |
| (2S,3R,4S,5R)-2-(6-(benzylamino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol |
| N6-BENZYL-D-ADENOSINE |
| BAP RIBOSIDE |
| N-Benzyladenosine |
| 6-BENZYLADENOSINE |
| N6-Benzyladenosine |
| (4S,2R,3R,5R)-2-hydroxymethyl-5-[6-(benzylamino)-purin-9-yl]-tetrahydrofuran-3,4-diol |
| Adenosine, N- (phenylmethyl)- |
| Benzyladenosine |
| 6-Benzylaminopurine Ribosiden |
| EINECS 224-298-9 |
| N-(Phenylmethyl)adenosine |
| (-)-N6-(benzyl)adenosine |
| MFCD00005740 |
