GSK-2606414

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H20F3N5O
Molecular Weight	451.4437
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C=C(C2=C(N)N=CN=C12)C3=CC4=C(C=C3)N(CC4)C(=O)CC5=CC(=CC=C5)C(F)(F)F

InChI

InChIKey=SIXVRXARNAVBTC-UHFFFAOYSA-N

InChI=1S/C24H20F3N5O/c1-31-12-18(21-22(28)29-13-30-23(21)31)15-5-6-19-16(11-15)7-8-32(19)20(33)10-14-3-2-4-17(9-14)24(25,26)27/h2-6,9,11-13H,7-8,10H2,1H3,(H2,28,29,30)

HIDE SMILES / InChI

Molecular Formula	C24H20F3N5O
Molecular Weight	451.4437
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22827572 | https://www.ncbi.nlm.nih.gov/pubmed/24107777

GSK2606414 is an orally bioavailable, potent, selective inhibitor of PERK. The drug may serve as a potential treatment for cancer and neurodegenerative diseases associated with the accumulation and aggregation of misfolded disease-specific proteins in the brain. GSK2606414 demonstrated good results on a mouse model of prion disease.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Eukaryotic translation initiation factor 2-alpha kinase 3 1 Target ID: Q9NZJ5 Gene ID: 9451.0 Gene Symbol: EIF2AK3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22827572	Inhibitor 8297		0.4 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22827572	Primary		Preclinical	Unknown Approved Use Unknown
Neurodegenerative diseases 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24107777	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Discovery of 7-methyl-5-(1-{[3-(trifluoromethyl)phenyl]acetyl}-2,3-dihydro-1H-indol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (GSK2606414), a potent and selective first-in-class inhibitor of protein kinase R (PKR)-like endoplasmic reticulum kinase (PERK).	2012 Aug 23	22827572

Patents

Sample Use Guides

In Vivo Use Guide

GSK2606414 was given orally twice a day for 21 days at doses of 50 and 150 mg/kg (preclinical study).

Route of Administration: Oral

In Vitro Use Guide

Lung carcinoma A549 cells were treated with GSK2606414 at doses of 0.03, 0.1 and 0.3 uM for 1 h to test the effect of the drug on cellular PERK phosphorylation.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:30:57 GMT 2023` Edited by `admin` on `Sat Dec 16 17:30:57 GMT 2023`
Record UNII	DPP2K6EFW8
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

GSK-2606414

Code

English

7-METHYL-5-(1-((3-(TRIFLUOROMETHYL)PHENYL)ACETYL)-2,3-DIHYDRO-1H-INDOL-5-YL)-7H-PYRROLO(2,3-D)PYRIMIDIN-4-AMINE

Systematic Name

English

1-(5-(4-AMINO-7-METHYL-7H-PYRROLO(2,3-D)PYRIMIDIN-5-YL)-2,3-DIHYDRO-1H-INDOL-1-YL)-2-(3-(TRIFLUOROMETHYL)PHENYL)ETHANONE

Systematic Name

English

1-(5-(4-AMINO-7-METHYLPYRROLO(2,3-D)PYRIMIDIN-5-YL)-2,3-DIHYDROINDOL-1-YL)-2-(3-(TRIFLUOROMETHYL)PHENYL)ETHANONE

Systematic Name

English

GSK2606414

Code

English

Ethanone, 1-[5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2,3-dihydro-1H-indol-1-yl]-2-[3-(trifluoromethyl)phenyl]-

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

GSK2606414