Kenpaullone

HCID 3820
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Basic information

CAS
142273-20-9
Standard SMILES
O=C1Cc2c([nH]c3ccc(Br)cc23)-c2ccccc2N1
InChIKey
QQUXFYAWXPMDOE-UHFFFAOYSA-N
Molecular formula
C16H11BrN2O
Average molar mass
327.17 g/mol
Monoisotopic mass
326.00547507

Overview

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, a cardioprotective agent, an EC 2.7.11.22 (cyclin-dependent kinase) inhibitor and an EC 2.7.11.26 (tau-protein kinase) inhibitor. It is an indolobenzazepine, a lactam and an organobromine compound. It is functionally related to a paullone.

Names & identifiers

Preferred name
Kenpaullone
IUPAC
9-bromo-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-one
English name
KENPAULLONE
Molecular formula
C16H11BrN2O
Molecular weight
327.18

Names & synonyms

kenpaullone142273-20-99-Bromopaullone9-Bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-oneNSC-664704NSC 6647049-Bromo-7,12-dihydroindolo(3,2-d)(1)benzazepin-6(5H)-oneT72H2BL53PCHEBI:92658DTXSID1016199414-bromo-8,18-diazatetracyclo(9.7.0.0^(2,7).0^(12,17))octadeca-1(11),2,4,6,12,14,16-heptaen-9-one14-bromo-8,18-diazatetracyclo[9.7.0.0^{2,7}.0^{12,17}]octadeca-1(11),2,4,6,12,14,16-heptaen-9-one
Show more names
KenpaullonCS-498KenpauLKenpaullone>9-BroMopaulloneNSC-664704(Kenpaullone)Kenpaullone Kenpaullone
RefChem:151101DTXCID50844859-bromo-5,12-dihydro-7H-benzo(2,3)azepino(4,5-b)indol-6-one634-310-89-bromo-7,12-dihydrobenzo[2,3]azepino[4,5-b]indol-6(5H)-oneIndolo[3,2-d][1]benzazepin-6(5H)-one, 9-bromo-7,12-dihydro-NSC6647049-bromo-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-one

Database identifiers

CAS
142273-20-9
PubChem CID
3820
DTXSID
DTXSID10161994
ChEMBL
CHEMBL296586
ChEBI
CHEBI:92658
UNII
T72H2BL53P
EC Number
634-310-8
Nikkaji
J485.726G

Properties

Computed structural properties

XLogP
3.3
Topological polar surface area
44.9 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
20

Physicochemical properties

Melting point
300 °C · >300°C (dec.)
Boiling point
613 · 613.0±45.0 °C(Predicted)
Density
1.596 · 1.596±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
18 mg/mL, · DMSO: 18 mg/mL, clear, yellow
form
Yellow-brown solid

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
hs_code
2933.79.1500
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Applications · 4 items

DescriptionKenpaullone (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

UsesKenpaullone has been used:as a glycogen synthase kinase 3 (GSK3)/ cyclin-dependent kinase (CDK) inhibitor to study its effects on human neural progenitor cell linesas an inhibitor of Krupple-like factor 4 (KLF4) in Gs-coupled designer GPCR (Gs DREADD= GsD) Agouti-related peptide (GsD-AgRP) miceas a GSK3/CDK inhibitor to study its effects on the sea urchin embryo development

UsesThe 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).

General DescriptionA 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.

Upstream & downstream products

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

1 records
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Compound notes

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