57500-07-9

Basic information

• Product Name: 6-BENZYLOXYPURINE
• Synonyms: 6-(Benzyloxy)-9H-purine;6-BENZYLOXYPURINE;6-Benzyloxypurine,99%;N-6-BENZYLOXYPURINE;6-PHENYLMETHOXY-5H-PURINE;6-BENZYLOXYPURINE 99%
• CAS NO: 57500-07-9
• Molecular Formula: C₁₂H₁₀N₄O
• Molecular Weight: 226.23
• Product Categories: Nucleosides, Nucleotides & Related Reagents;Building Blocks;Heterocyclic Building Blocks;Purines;Biochemistry;Nucleobases and their analogs
• Mol File: 57500-07-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 173-175 °C(lit.)
• Boiling Point: 508.3 °C at 760 mmHg
• Flash Point: 180.1 °C
• Appearance: /
• Density: 1.36 g/cm³
• Vapor Pressure: 5.95E-10mmHg at 25°C
• Refractive Index: 1.695
• PKA: 8.28±0.20(Predicted)
• CAS DataBase Reference: 6-BENZYLOXYPURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BENZYLOXYPURINE(57500-07-9)
• EPA Substance Registry System: 6-BENZYLOXYPURINE(57500-07-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 57500-07-9(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Synthesis Reference(s)

Synthetic Communications, 19, p. 1669, 1989 DOI: 10.1080/00397918908051065

InChI:InChI=1/C12H10N4O/c1-2-4-9(5-3-1)6-17-12-10-11(14-7-13-10)15-8-16-12/h1-5,7-8H,6H2,(H,13,14,15,16)

Upstream product

• 20194-18-7 sodium phenyl-methanolate 
• 87-42-3 6-chloropurine 
• 100-51-6 benzyl alcohol 
• 4316-98-7 6-chloro-4,5-diaminopyrimidine 
• 68-12-2 N,N-dimethyl-formamide 
• 87-42-3 6-chloro-7H-purine 
• 42204-35-3 O⁶-benzylinosine 

Downstream Products

• 825615-07-4 6-benzyloxy-9-Boc-purine 

Relevant articles and documents

Targeting nuclear protein TDP-43 by cell division cycle kinase 7 inhibitors: A new therapeutic approach for amyotrophic lateral sclerosis

Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease with no known cure. Aggregates of the nuclear protein TDP-43 have been recognized as a hallmark of proteinopathy in both familial and sporadic cases of ALS. Post-translational modifications of this protein, include hyperphosphorylation, cause disruption of TDP-43 homeostasis and as a consequence, promotion of its neurotoxicity. Among the kinases involved in these changes, cell division cycle kinase 7 (CDC7) plays an important role by directly phosphorylating TDP-43. In the present manuscript the discovery, synthesis, and optimization of a new family of selective and ATP-competitive CDC7 inhibitors based on 6-mercaptopurine scaffold are described. Moreover, we demonstrate the ability of these inhibitors to reduce TDP-43 phosphorylation in both cell cultures and transgenic animal models such as C. elegans and Prp-hTDP43 (A315T) mice. Altogether, the compounds described here may be useful as versatile tools to explore the role of CDC7 in TDP-43 phosphorylation and also as new drug candidates for the future development of ALS therapies.

N6-isopentenyladenosine a new potential anti-angiogenic compound that targets human microvascular endothelial cells in vitro

N6-isopentenyladenosine is an anti-proliferative and pro-apoptotic atypical nucleoside for normal and tumor cells. Considering the role of angiogenesis in various diseases, we investigated the cytotoxic effect of N6-isopentenyladenosine on human microvascular endothelial cells, protagonists in angiogenesis. Our results show that N6-isopentenyladenosine induced a significant reduction of cell viability, upregulated p21 and promoted caspase-3 cleavage in a dose dependent manner leading to apoptotic cell death as detected by FACS analysis. To understand structure-function relationship of N6-isopentenyladenosine, we investigated the effect of some N6-isopentenyladenosine analogs. Our results suggest that N6-isopentenyladenosine and some of its derivatives are potentially novel angiostatic agents and might be associated with other anti-angiogenic compounds for a better outcome.

An efficient synthesis of substituted cytosines and purines under focused microwave irradiation

A rapid nucleophilic displacement reaction of 6-chloropurine, 2-amino-6-chloropurine and 5-bromocytosine with various nucleophiles under focused microwave irradiation is described. Using this method, the desired products were obtained with the yields up to 99% in?a?short reaction time.