186692-44-4

Basic information

• Product Name: SELICICLIB
• Synonyms: 2-[[9-(1-methylethyl)-6-[(phenylmethyl)amino]-9H-purin-2-yl]amino]-1-Butanol
• CAS NO: 186692-44-4
• Molecular Formula: C₁₉H₂₆N₆O
• Molecular Weight: 354.455
• Mol File: 186692-44-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 577.5 °C at 760 mmHg
• Flash Point: 303.1 °C
• Appearance: /
• Density: 1.25
• Vapor Pressure: 3.52E-14mmHg at 25°C
• Refractive Index: 1.643
• CAS DataBase Reference: SELICICLIB(CAS DataBase Reference)
• NIST Chemistry Reference: SELICICLIB(186692-44-4)
• EPA Substance Registry System: SELICICLIB(186692-44-4)

Safety Data

• Hazardous Substances Data: 186692-44-4(Hazardous Substances Data)

Usage

General Description

Seliciclib, also known as roscovitine, is a selective and potent inhibitor of cyclin-dependent kinases (CDKs) that has shown promise in the treatment of cancer as well as other diseases. It has been found to inhibit CDK2, CDK7, and CDK9, which are involved in cell cycle regulation and transcription. This inhibition leads to cell cycle arrest and suppression of transcription of key proteins required for tumor growth and progression. Seliciclib has demonstrated anti-cancer activity in preclinical studies and has been investigated in clinical trials for various cancers, including breast, lung, and colorectal cancer. Additionally, it has also shown potential for the treatment of neurological and inflammatory diseases. However, further research is needed to fully understand its therapeutic potential and safety profile in humans.

InChI:InChI=1/C19H26N6O/c1-4-15(11-26)22-19-23-17(20-10-14-8-6-5-7-9-14)16-18(24-19)25(12-21-16)13(2)3/h5-9,12-13,15,26H,4,10-11H2,1-3H3,(H2,20,22,23,24)

Upstream product

• 203436-45-7 2,6-dichloro-9-isopropyl-9H-purine 
• 5451-40-1 2,6 dichloropurine 
• 39639-47-9 N⁶-benzyl-2-chloroadenine 
• 96-20-8 2-aminobutanol 
• 186692-41-1 2-chloro-6-phenylmethylamino-9-iso-propylpurine 

Downstream Products

• 1228315-33-0 [Pd(oxalate)(2-(1-ethyl-2-hydroxyethylamino)-N₆-(benzyl)-9-isopropyladenine)2] 

Relevant articles and documents

The first iron(III) complexes with cyclin-dependent kinase inhibitors: Magnetic, spectroscopic (IR, ES+ MS, NMR, 57Fe M?ssbauer), theoretical, and biological activity studies

The first FeIII complexes 1-6 with cyclin-dependent kinase (CDK) inhibitors of the type [Fe(Ln)Cl3]·nH2O (n=0 for 1, 1 for 2, 2 for 3-6; L1-L6=C2- and phenyl-substituted CDK inhibitors derived from 6-benzylamino-9-isopropylpurine), have been synthesized and characterized by elemental analysis, IR, 57Fe Mo?ssbauer, 1H and 13C NMR, and ES+ mass spectroscopies, conductivity and magnetic susceptibility measurements, and thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The study revealed that the compounds are mononuclear, tetrahedral high-spin (S=5/2) FeIII complexes with an admixture of an S=3/2 spin state originating probably from five-coordinated FeIII ions either connecting with a bidentate coordination mode of the CDK inhibitor ligand or relating to the possibility that one crystal water molecule enters the coordination sphere of the central atom in a portion of molecules of the appropriate complex. Nearly spin-only value of the effective magnetic moment (5.82μeff/μB) was determined for compound 1 due to absence of crystal water molecule(s) in the structure of the complex. Based on NMR data and DFT calculations, we assume that the appropriate organic ligand is coordinated to the FeIII ion through the N7 atom of a purine moiety. The cytotoxicity of the complexes was tested in vitro against selected human cancer cell lines (G-361, HOS, K-562 and MCF-7) along with the ability to inhibit the CDK2/cyclinE kinase. The best cytotoxicity (IC50: 4-23μM) and inhibition activity (IC50: 0.02-0.09μM) results have been achieved in the case of complexes 2-4, and complexes 3, 4 and 6, respectively. In addition, the X-ray structure of 2-chloro-6-benzylamino-9-isopropylpurine, i.e. a precursor for the preparation of L1, L4 and L5, is also described.