212844-54-7

Basic information

• Product Name: (2R)-2-[[6-[(3-CHLORO-4-CARBOXYPHENYL)AMINO]-9-(1-METHYLETHYL)-9H-PURIN-2-YL]AMINO]-3-METHYL-1-BUTANOL
• Synonyms: (2R)-2-[[6-[(3-CHLORO-4-CARBOXYPHENYL)AMINO]-9-(1-METHYLETHYL)-9H-PURIN-2-YL]AMINO]-3-METHYL-1-BUTANOL;PURVALANOL B;NG 95;(2R)-2-((6-((3-Chloro-4-carboxyphenyl)amino)-9-(1-methylethyl)-9H-purin-2-yl)amino)-3-methyl-1-butanol;NG 95, (2R)-2-[[6-[(3-Chloro-4-carboxyphenyl)amino]-9-(1-methylethyl)-9H-purin-2-yl]amino]-3-methyl-1-butanol;Purvalanol B(NG 95);Purvalanol B, >=96%;(R)-2-Chloro-4-((2-((1-hydroxy-3-methylbutan-2-yl)amino)-9-isopropyl-9H-purin-6-yl)amino)benzo
• CAS NO: 212844-54-7
• Molecular Formula: C20H25ClN6O3
• Molecular Weight: 432.9
• Product Categories: Signalling
• Mol File: 212844-54-7.mol
• Article Data: 0

Chemical Properties

• Melting Point: 58.5 °C
• Boiling Point: 660.6°Cat760mmHg
• Flash Point: 353.3°C
• Appearance: /solid
• Density: 1.43g/cm³
• Vapor Pressure: 2.37E-18mmHg at 25°C
• Refractive Index: 1.672
• Storage Temp.: −20°C
• Solubility: DMSO: 37 mg/mL, soluble
• PKA: 2.81±0.25(Predicted)
• CAS DataBase Reference: (2R)-2-[[6-[(3-CHLORO-4-CARBOXYPHENYL)AMINO]-9-(1-METHYLETHYL)-9H-PURIN-2-YL]AMINO]-3-METHYL-1-BUTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-[[6-[(3-CHLORO-4-CARBOXYPHENYL)AMINO]-9-(1-METHYLETHYL)-9H-PURIN-2-YL]AMINO]-3-METHYL-1-BUTANOL(212844-54-7)
• EPA Substance Registry System: (2R)-2-[[6-[(3-CHLORO-4-CARBOXYPHENYL)AMINO]-9-(1-METHYLETHYL)-9H-PURIN-2-YL]AMINO]-3-METHYL-1-BUTANOL(212844-54-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 212844-54-7(Hazardous Substances Data)

Usage

Description

(2R)-2-[[6-[(3-Chloro-4-carboxyphenyl)amino]-9-(1-methylethyl)-9H-purin-2-yl]amino]-3-methyl-1-butanol is a complex organic compound with a unique molecular structure. It is a derivative of purines, which are heterocyclic aromatic compounds that play a crucial role in biological systems, particularly in the formation of nucleic acids. (2R)-2-[[6-[(3-Chloro-4-carboxyphenyl)amino]-9-(1-methylethyl)-9H-purin-2-yl]amino]-3-methyl-1-butanol features a 2R configuration, indicating that it has a specific stereochemistry, which is essential for its biological activity and interactions with target molecules.

Uses

Used in Pharmaceutical Industry:
(2R)-2-[[6-[(3-Chloro-4-carboxyphenyl)amino]-9-(1-methylethyl)-9H-purin-2-yl]amino]-3-methyl-1-butanol is used as a cyclin-dependent kinase (CDK) inhibitor for cancer therapy. Cyclin-dependent kinases are key regulators of cell cycle progression, and their inhibition can lead to the arrest of cancer cell growth and proliferation. (2R)-2-[[6-[(3-Chloro-4-carboxyphenyl)amino]-9-(1-methylethyl)-9H-purin-2-yl]amino]-3-methyl-1-butanol has shown potent inhibitory activity against several CDKs, including Cdk2/cyclin A, Cdk2/cyclin E, Cdk5/p35, and Cdk2/cyclin B, with IC50 values in the nanomolar range.
Used in Antiviral Applications:
(2R)-2-[[6-[(3-Chloro-4-carboxyphenyl)amino]-9-(1-methylethyl)-9H-purin-2-yl]amino]-3-methyl-1-butanol is used as an antiviral agent, particularly against Plasmodium parasites, which are responsible for malaria. At micromolar doses, this compound has demonstrated the ability to inhibit the growth of these parasites, offering a potential therapeutic approach for the treatment of malaria and other parasitic infections.

Biological Activity

Cyclin-dependent kinase inhibitor. IC 50 values are 6, 6, 9, > 10,000, and 6 nM for cdc2/cyclin B, cdk2/cyclin A, cdk2/cyclin E, cdk4/cyclin D1 and cdk5-p35 respectively. Selective over a range of other protein kinases (IC 50 > 10,000 nM). Shown to have antiproliferative properties, mediated by p42/p44 MAPK.

InChI:InChI=1/C20H25ClN6O3/c1-10(2)15(8-28)24-20-25-17(16-18(26-20)27(9-22-16)11(3)4)23-12-5-6-13(19(29)30)14(21)7-12/h5-7,9-11,15,28H,8H2,1-4H3,(H,29,30)(H2,23,24,25,26)/t15-/m0/s1

Downstream Products

• 1450754-54-7 C₂₇H₃₄ClN₉O₂ 
• 1450754-53-6 C₂₂H₂₇ClN₆O₄