7247-96-3

Basic information

• Product Name: 6-chloro-9-octyl-9H-purine
• CAS NO: 7247-96-3
• Molecular Formula: C₁₃H₁₉ClN₄
• Molecular Weight: 266.7698
• Mol File: 7247-96-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 397.4°C at 760 mmHg
• Flash Point: 194.2°C
• Density: 1.22g/cm³
• Vapor Pressure: 1.59E-06mmHg at 25°C
• Refractive Index: 1.602
• CAS DataBase Reference: 6-chloro-9-octyl-9H-purine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-9-octyl-9H-purine(7247-96-3)
• EPA Substance Registry System: 6-chloro-9-octyl-9H-purine(7247-96-3)

Safety Data

• Hazardous Substances Data: 7247-96-3(Hazardous Substances Data)

Usage

Chemical compound

6-chloro-9-octyl-9H-purine

Class

Purine derivatives

Structure

Chlorine substitution at 6-position, octyl group attached to 9-position

Potential applications

Pharmaceutical research, drug development

Uses

Building block for synthesis of pharmaceutical compounds, targeting purine receptors/enzymes in purine metabolism

Potential benefits

Development of anticancer/antiviral drugs, study of purine biological pathways

Need for further research

Biological and pharmacological properties

Upstream product

• 111-83-1 1-bromo-octane 
• 87-42-3 6-chloropurine 
• 111-87-5 octanol 

Relevant articles and documents

Synthesis and anticonvulsant activity of novel purine derivatives

A series of new purines containing triazole and other heterocycle substituents was synthesized and evaluated for their preliminary anticonvulsant activity and neurotoxicity by using the maximal electroshock (MES), subcutaneous pentylenetetrazole (scPTZ) and rotarod neurotoxicity (TOX) tests. Among the compounds studied, 9-decyl-6-(1H-1,2,4-triazol-1-yl)-9H-purine (5e) was the most potent compound, with a median effective dose of 23.4 mg/kg and a high protective index of more than 25.6 after intraperitoneal administration in mice. Compound 5e showed significant oral activity against MESinduced seizures in mice, with an ED50 of 39.4 mg/kg and a PI above 31.6. These results demonstrate that compound 5e possesses better anticonvulsant activity and is safer than the commercially available drugs carbamazepine and valproate in MES, scPTZ and TOX models.

Synthesis, C-13 NMR, and X-ray crystal structure of N6,N9-octamethylenepurinecyclophane

The synthesis and structure determination of N6,N9-octamethylenepurine cyclophane by single crystal X-ray diffraction is reported.The cyclophane was prepared from 6-chloropurine and 8-aminooctanoic acid as starting materials.The aminooctyl fragment was first attached to N9 of 6-chloropurine by means of the Mitsunobu reaction and cyclization to the cyclophane effected by nucleophilic attack of the amino group at the C6 position and displacement of chloride ion.Reversing the reaction strategy did not result in formation of the cyclophane.Crystals of the cyclophane were monoclinic, P21/n, a = 9.620(3), b = 12.266(3), c = 11.994(2), Angstroem, β = 111.25(2) deg, Z = 4.Intensities were measured with a Nicolet P3 diffractometer and MoKα radiation at room temperature.The structure was solved by direct methods and refined to R = 0.0683, Rw = 0.0493 based on 1730 reflections.The molecule shows some strain, but bond lenghts and angles are normal.Attempts to relieve the strain are made by a small distortion of the purine rings and bending of the N6 and C8' atoms out of the planes to which they are attached (0.314(4), 0.459(5) Angstroem).Further, the N6,H6,C1' group is twisted by 30 deg from the pyrimidine plane and the torsion angles in the aliphatic chain are distorted from the idealized 60, 120, 180 deg (average, 13.6 deg; range 5.1-24.9 deg).These distortions result in some weakening of the ?-bonding in the adenine moiety. Key words: purinophane synthesis, nucleophilic aromatic substitution, conformational analysis, crystal structure.