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ChemicalBook--->CAS DataBase List--->142273-20-9

142273-20-9

142273-20-9 Structure

142273-20-9 Structure
IdentificationMore
[Name]

KENPAULLONE
[CAS]

142273-20-9
[Synonyms]

CS-498
KenpauL
Kenpaullon
NSC-664704
KENPAULLONE
Kenpaullone>
9-BroMopaullone
NSC664704;NSC 664704
Kenpaullone Kenpaullone
NSC-664704(Kenpaullone)
Kenpaullone (NSC-664704)
NSC664704;NSC 664704;9-BROMOPAULLONE
Kenpaullone - CAS 142273-20-9 - Calbiochem
9-bromo-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-one
9-BROMO-7,12-DIHYDRO-INDOLO[3,2-D][1]BENZAZEPIN-6(5H)-ONE
8-BROMO-7,12-DIHYDRO-INDOLO[3,2-D][1]-BENZAZEPIN-6(5H)-ONE
9-Bromo-7,12-dihydrobenzo[2,3]azepino[4,5-b]indol-6(5H)-one
Indolo[3,2-d][1]benzazepin-6(5H)-one, 9-bromo-7,12-dihydro-
9-Bromo-7,12-dihydro-indolo[3,2-d][1]benzazepin-6(5H)-one, NSC 664704
Kenpaullone 9-Bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
[Molecular Formula]

C16H11BrN2O
[MDL Number]

MFCD02683595
[Molecular Weight]

327.18
[MOL File]

142273-20-9.mol
Chemical PropertiesBack Directory
[Appearance]

Tan Solid
[Melting point ]

>300°C (dec.)
[Boiling point ]

613.0±45.0 °C(Predicted)
[density ]

1.596±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

DMSO: 18 mg/mL, clear, yellow
[form ]

Yellow-brown solid
[pka]

14.29±0.20(Predicted)
[color ]

yellow
[Usage]

The paullones are a novel class of kinase inhibitors, initially identified as CDK inhibitors. Kenpaullone has been found to be a useful GSK-3?inhibitor (IC50=23nM).
[Stability:]

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
[InChIKey]

QQUXFYAWXPMDOE-UHFFFAOYSA-N
[CAS DataBase Reference]

142273-20-9(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[WGK Germany ]

3
[HS Code ]

2933.79.1500
Hazard InformationBack Directory
[Description]

Kenpaullone (142273-20-9) inhibits GSK-3β (IC50=0.23 μM) as well as several cyclin-dependent kinases (CDKs), IC50=0.4, 0.68 and 0.85 μM for cdk1, cdk2 and cdk5 respectively.1-3 Induces pluripotent stem cells from somatic cells4 and increases direct neural conversion of human fibroblasts5 when used with other small molecules. Inhibits Kruppel-Like Factor 4 (KLF4) reducing autoimmune arthritis in the collagen-induced arthritis mouse model.6
[Chemical Properties]

Tan Solid
[Uses]

The paullones are a novel class of kinase inhibitors, initially identified as CDK inhibitors. Kenpaullone has been found to be a useful GSK-3?inhibitor (IC50=23nM).
[Uses]

The paullones are a novel class of kinase inhibitors, initially identified as CDK inhibitors. Kenpaullone has been found to be a useful GSK-3? inhibitor (IC50=23nM).
[Definition]

ChEBI: Kenpaullone is an indolobenzazepine that is paullone in which the hydrogen at position 9 is replaced by a bromo substituent. It is an ATP-competitive inhibitor of cyclin-dependent kinases (CDKs) and glycogen synthase kinase 3beta (GSK3beta). It has a role as a geroprotector, an EC 2.7.11.26 (tau-protein kinase) inhibitor, a cardioprotective agent and an EC 2.7.11.22 (cyclin-dependent kinase) inhibitor. It is an indolobenzazepine, a lactam and an organobromine compound. It is functionally related to a paullone.
[General Description]

A potent, cell-permeable, and reversible inhibitor of glycogen synthase kinase-3β (IC50 = 230 nM), Lck (IC50 = 470 nM), and cyclin-dependent kinases (Cdks). Inhibits Cdk1/cyclin B (IC50 = 400 nM), Cdk2/cyclin A (IC50 = 680 nM), Cdk2/cyclin E (IC50 = 7.5 μM), and Cdk5/p25 (IC50 = 850 nM). Also inhibits other kinases such as c-Src (IC50 = 15 μM), casein kinase II (IC50 = 20 μM), ERK1 (IC50 = 20 μM), and ERK2 (IC50 = 9 μM). Inhibition is competitive with respect to ATP binding.
[Biological Activity]

Potent inhibitor of CDK1/cyclin B and GSK-3 β (IC 50 values are 0.4 and 0.23 μ M respectively). Also inhibits CDK2/cyclin A, CDK2/cyclin E and CDK5/cyclin/p35 (IC 50 values are 0.68, 7.5 and 0.85 μ M respectively). Selective over c-src (IC 50 = 15 μ M), casein kinase 2 (IC 50 = 20 μ M), ERK1 (IC 50 = 20 μ M), ERK2 (IC 50 = 9 μ M) and a range of other protein kinases (IC 50 values > 35 μ M). Generates induced pluripotent stem cells (iPSCs) from somatic cells when used in combination with reprogramming factors; can replace Klf4.
[Biochem/physiol Actions]

Kenpaullone is also an inhibitor of glycogen synthase kinase 3β (GSK3β).?It also inhibits cyclin-dependent kinase 1 (CDK1/cyclin B), CDK2/cyclin A, CDK2/cyclin E, and CDK5/p25, majorly by competitive inhibition of adenosine triphosphate (ATP) binding.
[storage]

Store at RT
[References]

Zaharevitz et al. (1999), Discovery and initial characterization of the paullones, a novel class of small-molecule inhibitors of cyclin-dependent kinases; Cancer Res. 59 2566 Schultz et al. (1999) Paullones, a series of cyclin-dependent kinase inhibitor: synthesis, evaluation of CDK1/cyclin B inhibition, and in vitro antitumor activity; J.Med.Chem. 42 2909 Bain et al. (2003), The specificities of protein kinase inhibitors: an update; J. 371(Pt. 1) 199 Lyssiotis et al. (2009) Reprogramming of murine fibroblasts to induced pluripotent stem cells with chemical complementation of Klf4; Natl. Acad. Sci. USA 106 8912 Pfisterer et al. (2016), Small molecules increase direct neural conversion of human fibroblasts; Rep. 6 38290 Choi et al. (2018), Kruppel-Like Factor 4 Positively Regulates Autoimmune Arthritis in Mouse Models and Rheumatoid Arthritis in Patients via Modulating Cell Survival and Inflammation Factors of Fibroblast-Like Synoviocyte; Immunol. 9 1339
Spectrum DetailBack Directory
[Spectrum Detail]

KENPAULLONE(142273-20-9)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

142273-20-9(sigmaaldrich)
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