39639-47-9

Basic information

• Product Name: N-Benzyl-2-chloro-9H-purin-6-amine
• Synonyms: N-Benzyl-2-chloro-9H-purin-6-amine;2-Chloro-N-(phenylmethyl)-1H-purin-6-amine;6-Benzylamino-2-chloropurine
• CAS NO: 39639-47-9
• Molecular Formula: C₁₂H₁₀ClN₅
• Molecular Weight: 259.6943
• Mol File: 39639-47-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 239-241℃
• Boiling Point: 509.699 °C at 760 mmHg
• Flash Point: 262.057 °C
• Appearance: /
• Density: 1.49
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.765
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform, DMSO, Ethyl Acetate
• CAS DataBase Reference: N-Benzyl-2-chloro-9H-purin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzyl-2-chloro-9H-purin-6-amine(39639-47-9)
• EPA Substance Registry System: N-Benzyl-2-chloro-9H-purin-6-amine(39639-47-9)

Safety Data

• Hazardous Substances Data: 39639-47-9(Hazardous Substances Data)

Usage

Description

N-Benzyl-2-chloro-9H-purin-6-amine is an organic compound with the molecular formula C11H9ClN6. It is a derivative of purine, a heterocyclic compound that is a central part of the structure of nucleic acids, such as DNA and RNA. N-Benzyl-2-chloro-9H-purin-6-amine features a benzyl group attached to the nitrogen atom at position 9, a chlorine atom at position 2, and an amine group at position 6. Its chemical structure and properties make it a valuable intermediate in the synthesis of various biologically active molecules.

Uses

Used in Pharmaceutical Industry:
N-Benzyl-2-chloro-9H-purin-6-amine is used as an intermediate in the synthesis of Olomoucine (O567000), a purine derivative with significant biological activity. Olomoucine is known to inhibit cyclin-dependent kinases, which play a crucial role in regulating cell cycle progression. By inhibiting these kinases, Olomoucine can induce G1 arrest, effectively halting the cell cycle and preventing uncontrolled cell proliferation, a hallmark of cancer. This makes N-Benzyl-2-chloro-9H-purin-6-amine an essential component in the development of potential anticancer drugs.
Additionally, due to its unique chemical structure, N-Benzyl-2-chloro-9H-purin-6-amine may also be used as a building block for the synthesis of other purine-based compounds with various applications in the pharmaceutical industry, such as antiviral, anti-inflammatory, and immunosuppressive agents.

InChI:InChI=1/C12H10ClN5/c13-12-17-10(9-11(18-12)16-7-15-9)14-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H2,14,15,16,17,18)

Upstream product

• 5451-40-1 2,6 dichloropurine 
• 100-46-9 benzylamine 
• 700-02-7 adenine 1-oxide 
• 5167-14-6 hypoxanthine 1-N-oxide 
• 100-39-0 benzyl bromide 
• 149948-29-8 C₈H₉ClN₆ 
• 190962-00-6 6-chloro-2-formylaminopurine acetate 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 10310-21-1 2-Amino-6-chloropurin 
• 5451-40-1 2,6-dichloro-7H-purine 

Downstream Products

• 101622-53-1 2-chloro-6-benzylamino-9-methylpurine 
• 137201-22-0 2-Chloro-9-methyl-6-benzylmethylaminopurine 
• 186692-41-1 2-chloro-6-phenylmethylamino-9-iso-propylpurine 
• 70608-06-9 2-(2-hydroxyethylamino)-6-benzylaminopurine 
• 39639-54-8 N²,N⁶-dibenzyl-7⁽⁹⁾H-purine-2,6-diamine 
• 101622-51-9 olomoucine 
• 158982-15-1 N9-Isopropyl olomoucine 
• 186692-44-4 roscovitine 
• 186692-46-6 roscovitine 
• 186692-45-5 (S)-roscovitine 
• 137201-23-1 2-Aminomethyl-9-methyl-6-benzylaminopurine 
• 137201-13-9 2-(2-hydroxyisobutylamino)-6-benzylamino-9-methylpurine 
• 1012864-71-9 methyl 1-[N⁶-benzyl-2-chloroadenin-9-yl]-2,3-di-O-acetyl-β-D-ribofuronate 
• 1007556-16-2 N-benzyl-9-butyl-2-chloro-9H-purin-6-amine 

Relevant articles and documents

Synthesis and biological evaluation of seliciclib derivatives as potent and selective CDK9 inhibitors for prostate cancer therapy

Seliciclib is a cyclin-dependent kinase (CDK) inhibitor that has been assayed in phase II clinical trials as an anticancer agent. This paper describes the synthesis of novel derivatives of seliciclib with improved potency, metabolic stability, aqueous solubility, and anti-proliferative activity. The new derivatives showed a novel CDKs selectivity profile. Replacement of ethyl alcohol at position 2 of purine with dimethylaminopropyl and fluorination of benzyl at position 6 of purine of seliciclib resulted in the formation of a derivative that potently and selectively inhibited CDK9 (26?nM vs. CDK9 and > 60-fold selectivity vs. CDK2/5/7). In comparison to seliciclib, this derivative shows lower metabolic clearance (25% lower in Clint), higher aqueous solubility and is more cytotoxic in androgen-independent prostate cancer cells. Graphic abstract: [Figure not available: see fulltext.].

COMPOUNDS AS INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR

The present invention provides compounds of Formula (I) shown above and their pharmaceutically acceptable salt, solvates, isomers, or prodrugs, as well as pharmaceutical compositions containing these compounds. Also provided by the invention is a method for treating a disorder mediated by macrophage migration inhibitory factor in a subject, comprising administering to the subject in need thereof a compound or a pharmaceutical composition of this invention.

IMAGING AGENTS FOR NEURAL FLUX

Provided herein are radiolabeled compounds useful for non-invasive imaging techniques. An exemplary radiolabeled compound provided herein is useful as a radiotracer for positron emission tomography. The present application also provides unlabeled compounds useful in methods of treating diseases of the central nervous system or disease of the peripheral nervous system. Methods for preparing radiolabeled compounds, preparing unlabeled compounds, and diagnostic methods using labeled or unlabeled compounds are also provided.