500568-72-9

Basic information

• Product Name: 2-Chloro-6-(2-hydroxybenzylamino)-9-isopropylpurine
• Synonyms: 2-[[[2-Chloro-9-(1-methylethyl)-9H-purin-6-yl]amino]methyl]-phenol;2-Chloro-6-(2-hydroxybenzylamino)-9-isopropylpurine
• CAS NO: 500568-72-9
• Molecular Formula: C₁₅H₁₆ClN₅O
• Molecular Weight: 317.77
• Product Categories: Aromatics Compounds;Aromatics;Bases & Related Reagents;Heterocycles;Nucleotides
• Mol File: 500568-72-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 472.594°C at 760 mmHg
• Flash Point: 239.617°C
• Appearance: /
• Density: 1.425g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.69
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Very Slightly)
• PKA: 9.81±0.30(Predicted)
• CAS DataBase Reference: 2-Chloro-6-(2-hydroxybenzylamino)-9-isopropylpurine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-6-(2-hydroxybenzylamino)-9-isopropylpurine(500568-72-9)
• EPA Substance Registry System: 2-Chloro-6-(2-hydroxybenzylamino)-9-isopropylpurine(500568-72-9)

Safety Data

• Hazardous Substances Data: 500568-72-9(Hazardous Substances Data)

Usage

Description

2-Chloro-6-(2-hydroxybenzylamino)-9-isopropylpurine, with the chemical abstracts service number 500568-72-9, is a synthetic organic compound that holds significant value in the field of organic synthesis. 2-Chloro-6-(2-hydroxybenzylamino)-9-isopropylpurine is characterized by its unique molecular structure, which features a chloro group at the 2nd position, a hydroxybenzylamino group at the 6th position, and an isopropyl group at the 9th position on a purine scaffold. Its versatile chemical properties make it a promising building block for the development of various pharmaceuticals and other organic compounds.

Uses

Used in Organic Synthesis:
2-Chloro-6-(2-hydroxybenzylamino)-9-isopropylpurine is used as a key intermediate in organic synthesis for the creation of a wide range of chemical products. Its unique functional groups and structural features allow it to participate in various chemical reactions, facilitating the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Chloro-6-(2-hydroxybenzylamino)-9-isopropylpurine is utilized as a precursor in the development of new drugs. Its ability to form diverse chemical entities makes it a valuable component in medicinal chemistry, potentially leading to the discovery of novel therapeutic agents with improved efficacy and selectivity.
Used in Chemical Research:
2-Chloro-6-(2-hydroxybenzylamino)-9-isopropylpurine also serves as a valuable research tool in chemical research. It can be employed to study reaction mechanisms, explore new synthetic methodologies, and investigate the properties of various chemical systems, thereby contributing to the advancement of chemical science.

InChI:InChI=1/C15H16ClN5O/c1-9(2)21-8-18-12-13(19-15(16)20-14(12)21)17-7-10-5-3-4-6-11(10)22/h3-6,8-9,22H,7H2,1-2H3,(H,17,19,20)

Upstream product

• 932-30-9 2-Hydroxybenzylamine 
• 203436-45-7 2,6-dichloro-9-isopropyl-9H-purine 
• 5451-40-1 2,6 dichloropurine 
• 5451-40-1 2,6-dichloro-7H-purine 

Downstream Products

• 500735-47-7 Olomoucine II 
• 471270-60-7 6-(2-hydroxybenzylamino)-2-(3-hydroxypropylamino)-9-isopropylpurine 
• 1427518-48-6 C₂₀H₂₈N₆O₂ 
• 1427518-49-7 C₁₉H₂₆N₆O 

Relevant articles and documents

Synthesis and in vitro biological evaluation of 2,6,9-trisubstituted purines targeting multiple cyclin-dependent kinases

Several inhibitors of cyclin-dependent kinases (CDKs), including the 2,6,9-trisubstituted purine derivative roscovitine, are currently being evaluated in clinical trials as potential anticancer drugs. Here, we describe a new series of roscovitine derivatives that show increased potency in vitro. The series was tested for cytotoxicity against six cancer cell lines and for inhibition of CDKs. For series bearing 2-(hydroxyalkylamino) moiety, cytotoxic potency strongly correlated with anti-CDK2 activity. Importantly, structural changes that increase biochemical and anticancer activities of these compounds also increase elimination half-life. The most potent compounds were investigated further to assess their ability to influence cell cycle progression, p53-regulated transcription and apoptosis. All the observed biological effects were consistent with inhibition of CDKs involved in the regulation of cell cycle and transcription.

Synthesis and biological activity of olomoucine II.

Based on our previous experiences with synthesis of purines, novel 2,6,9-trisubstituted purine derivatives were prepared and assayed for the ability to inhibit CDK1/cyclin B kinase. One of newly synthesized compounds designated as olomoucine II, 6-[(2-hydroxybenzyl)amino]-2-[[1-(hydroxymethyl)propyl]amino]-9-isopropylpurine, displays 10 times higher inhibitory activity than roscovitine, potent and specific CDK1 inhibitor. Olomoucine II in vitro cytotoxic activity exceeds purvalanol A, the most potent CDK inhibitor, as it kills the CEM cells with IC(50) value of 3.0 microM.