2382-10-7

Basic information

• Product Name: 2,6-DICHLORO-9-METHYL-9H-PURINE
• Synonyms: 2,6-DICHLORO-9-METHYL-9H-PURINE;2,6-Dichloro-9-Methylpurine;9-Methyl-2,6-dichloropurine
• CAS NO: 2382-10-7
• Molecular Formula: C₆H₄Cl₂N₄
• Molecular Weight: 203.03
• Mol File: 2382-10-7.mol
• Article Data: 27

Chemical Properties

• Melting Point: 152-153℃
• Boiling Point: 307.2°C at 760 mmHg
• Flash Point: 139.6°C
• Appearance: /
• Density: 1.76
• Vapor Pressure: 0.000733mmHg at 25°C
• Refractive Index: 1.76
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.90±0.10(Predicted)
• CAS DataBase Reference: 2,6-DICHLORO-9-METHYL-9H-PURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DICHLORO-9-METHYL-9H-PURINE(2382-10-7)
• EPA Substance Registry System: 2,6-DICHLORO-9-METHYL-9H-PURINE(2382-10-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 2382-10-7(Hazardous Substances Data)

Usage

Description

2,6-DICHLORO-9-METHYL-9H-PURINE is an organic compound with the molecular formula C6H5Cl2N5. 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. This specific compound is characterized by the presence of two chlorine atoms at the 2nd and 6th positions and a methyl group at the 9th position.

Uses

Used in Pharmaceutical Industry:
2,6-DICHLORO-9-METHYL-9H-PURINE is used as a reagent for the synthesis of highly selective inhibitors of PI3K-δ (Phosphoinositide 3-kinase delta). These inhibitors are crucial in the treatment of inflammatory diseases, particularly those related to leukocytes, which are white blood cells that play a vital role in the immune system. By targeting PI3K-δ, these inhibitors can help regulate the immune response and alleviate the symptoms of various leukocyte-related illnesses.

InChI:InChI=1/C6H4Cl2N4/c1-12-2-9-3-4(7)10-6(8)11-5(3)12/h2H,1H3

Upstream product

• 74-87-3 methylene chloride 
• 5451-40-1 2,6 dichloropurine 
• 74-83-9 methyl bromide 
• 69-89-6 xanthin 
• 5451-40-1 2,6-dichloro-7H-purine 
• 74-88-4 methyl iodide 
• 5451-40-1 2,6-dichloropurine 
• 1198-33-0 9-methylxanthine 

Downstream Products

• 925254-29-1 2-chloro-N-cyclohexyl-9-methyl-9H-purin-6-amine 
• 1062592-41-9 (2-chloro-9-methyl-9H-purin-6-yl)-(4-chloro-phenyl)-amine 
• 1055926-73-2 1,1-dimethylethyl 2-(2-chloro-9-methyl-9H-purin-6-yl)-2-cyclo-hexyl-hydrazine-carboxylate 
• 552315-10-3 (2,6-difluoro-phenyl)-[2-(4-fluoro-2-methyl-phenyl)-9-methyl-9H-purin-6-yl]-amine 
• 672958-34-8 (4-chloro-phenyl)-[2-(4-fluoro-2-methyl-phenyl)-9-methyl-9H-purin-6-yl]-amine 
• 672958-31-5 [2-(4-fluoro-2-methyl-phenyl)-9-methyl-9H-purin-6-yl]-(2-methoxy-phenyl)-amine 
• 672958-33-7 [2-(4-fluoro-2-methyl-phenyl)-9-methyl-9H-purin-6-yl]-(4-fluoro-phenyl)-amine 
• 672958-64-4 [2-(4-fluoro-2-methyl-phenyl)-9-methyl-9H-purin-6-yl]-phenyl-amine 
• 552315-09-0 2-(4-fluoro-2-methyl-phenyl)-6-methanesulfonyl-9-methyl-9H-purine 
• 672958-59-7 2-(4-fluoro-2-methyl-phenyl)-9-methyl-6-methylsulfanyl-9H-purine 
• 30720-65-1 2,6-Diamino-9-methylpurine 
• 101622-53-1 2-chloro-6-benzylamino-9-methylpurine 
• 5502-78-3 9-Methylguanine 

Relevant articles and documents

Purine-based Ir(iii) complexes for sensing viscosity of endo-plasmic reticulum with fluorescence lifetime imaging microscopy

Novel purine-based iridium complexes were designed for selective determination of ER viscosity. TheIr-PHpossessed excellent ER targeting ability and could distinguish the viscosity changes under ER stress by fluorescence lifetime image microscopy (FLIM),

Structure-Based Optimization of Quinazolines as Cruzain and TbrCATL Inhibitors

The cysteine proteases, cruzain and TbrCATL (rhodesain), are therapeutic targets for Chagas disease and Human African Trypanosomiasis, respectively. Among the known inhibitors for these proteases, we have described N4-benzyl-N2-phenylquinazoline-2,4-diamine (compound 7 in the original publication, 1a in this study), as a competitive cruzain inhibitor (Ki = 1.4 μM). Here, we describe the synthesis and biological evaluation of 22 analogs of 1a, containing modifications in the quinazoline core, and in the substituents in positions 2 and 4 of this ring. The analogs demonstrate low micromolar inhibition of the target proteases and cidal activity against Trypanosoma cruzi with up to two log selectivity indices in counterscreens with myoblasts. Fourteen compounds were active against Trypanosoma brucei at low to mid micromolar concentrations. During the optimization of 1a, structure-based design and prediction of physicochemical properties were employed to maintain potency against the enzymes while removing colloidal aggregator characteristics observed for some molecules in this series.

Discovery of novel 9H-purin derivatives as dual inhibitors of HDAC1 and CDK2

HDAC and CDK inhibitors have been demonstrated to be synergistically in suppressing cancer cell proliferation and inducing apoptosis. In this work, we incorporated the pharmacophore groups of HDACs and CDKs inhibitors into one molecule to design and synthesize a series of purin derivatives as HDAC/CDK dual inhibitors. The lead compound 6d, showing good HDAC1 and CDK2 inhibitory activity with IC50 values of 5.8 and 56 nM, respectively, exhibited attractive potency against several cancer cell lines in vitro. This work may lead to the discovery of a novel scaffold and potential dual HDAC/CDK inhibitors.