101622-53-1

Basic information

• Product Name: 2-CHLORO-6-BENZYLAMINO-9-METHYLPURINE
• Synonyms: 2-CHLORO-6-BENZYLAMINO-9-METHYLPURINE;Benzyl-(2-chloro-9-methyl-9H-purin-6-yl)-amine;2-Chloro-9-Methyl-6-(benzylaMino)purine;2-Chloro-9-methyl-N-(phenylmethyl)-9H-purin-6-amine;6-(Benzylamino)-2-chloro-9-methylpurine
• CAS NO: 101622-53-1
• Molecular Formula: C₁₃H₁₂ClN₅
• Molecular Weight: 273.72088
• Mol File: 101622-53-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 443.1°C at 760 mmHg
• Flash Point: 221.8°C
• Appearance: /
• Density: 1.40±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 4.77E-08mmHg at 25°C
• Refractive Index: 1.702
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DCM (Slightly), Ethyl Acetate (Slightly), Methanol (Sligh
• CAS DataBase Reference: 2-CHLORO-6-BENZYLAMINO-9-METHYLPURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-6-BENZYLAMINO-9-METHYLPURINE(101622-53-1)
• EPA Substance Registry System: 2-CHLORO-6-BENZYLAMINO-9-METHYLPURINE(101622-53-1)

Safety Data

• Hazardous Substances Data: 101622-53-1(Hazardous Substances Data)

Usage

Description

2-Chloro-6-benzylamino-9-methylpurine is a chemical compound that serves as an intermediate in the synthesis of Olomoucine (O567000), a purine derivative with significant biological activity. 2-CHLORO-6-BENZYLAMINO-9-METHYLPURINE plays a crucial role in the development of pharmaceuticals targeting specific cellular processes.

Uses

Used in Pharmaceutical Industry:
2-Chloro-6-benzylamino-9-methylpurine is used as a key intermediate in the synthesis of Olomoucine (O567000) for its potential applications in cancer research and therapy. Olomoucine, as a cyclin-dependent kinase inhibitor, is known to induce G1 arrest, which can be beneficial in controlling cell proliferation in cancer cells.
Additionally, this compound may be utilized in the development of other purine-based drugs, given its structural properties and potential interactions with cellular targets. Its role in the synthesis of bioactive molecules highlights its importance in the advancement of medicinal chemistry and drug discovery.

InChI:InChI=1/C13H12ClN5/c1-19-8-16-10-11(17-13(14)18-12(10)19)15-7-9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,15,17,18)

Upstream product

• 2382-10-7 2,6-dichloro-9-methyl-9H-purine 
• 100-46-9 benzylamine 
• 39639-47-9 N⁶-benzyl-2-chloroadenine 
• 74-88-4 methyl iodide 
• 700-02-7 adenine 1-oxide 
• 5451-40-1 2,6 dichloropurine 
• 5167-14-6 hypoxanthine 1-N-oxide 

Downstream Products

• 101622-51-9 olomoucine 
• 137201-13-9 2-(2-hydroxyisobutylamino)-6-benzylamino-9-methylpurine 
• 288305-89-5 (R)-6-(benzylamino)-2-[[(1-hydroxymethyl)propyl]amino]-9-methylpurine 

Relevant articles and documents

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.

CALCIUM CHANNEL AGONISTS

Embodiments of calcium channel agonists, as well as methods of making and using the calcium channel agonists, are disclosed. The disclosed calcium channel agonists and corresponding salt forms have a structure according to general formula I wherein each bond depicted as " " is a single bond or a double bond as needed to satisfy valence requirements; Z1, Z2, Z3, Z4, and Z5 independently are nitrogen or carbon; R1 and R3 are alkyl; R2 is alkyl, aryl, heteroaryl, arylalkyl, or heteroarylalkyl; and R4 is alkyl or hydroxyalkyl.

Synthesis and biological activities of C-2, N-9 substituted 6- benzylaminopurine derivatives as cyclin-dependent kinase inhibitor

In this study, C-2, N-9 substituted 6-benzylaminopurine derivatives were synthesized and their inhibitory effects on cyclin-dependent kinase (CDK2) were evaluated. The effect of substituents at the C-2 and N-9 positions of substituted purine was investigated. Among the compounds tested, compound 7b- iii (6-benzylamino-2-thiomorpholinyl-9-isopropylpurine) was the most active inhibitor (IC50 = 0.9 μM). Compound 7b-iii showed 10-fold higher activity compared to olomoucine and almost the same activity as roscovitine. Results from structure-activity relationship studies should allow the design of more potent and selective CDK inhibitors, which may provide an effective therapy for cancer or other CDK dependent diseases.