937174-76-0

Basic information

• Product Name: 4-[2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-[(3S)-3-piperidinylmethoxy]-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol
• Synonyms: 4-[2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-[(3S)-3-piperidinylmethoxy]-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol;GSK 690693;(R)-4-(2-(4-AMINO-1,2,5-OXADIAZOL-3-YL)-1-ETHYL-7-(PIPERIDIN-3-YLMETHOXY)-1H-IMI;(S)-4-(2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-(piperidin-3-ylmethoxy)-1H-imidazo[4,5-c]pyridi;4-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-((S)-piperidin-3-ylmethoxy)-1H-imidazo[4,5-c]pyridin-4-yl)-2-methylbut-3-yn-2-ol;4-[2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-[(3S)-3-piperidinylmethoxy]-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol GSK 690693;4-(2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-{[(3S)-3-piperidinylmethyl]oxy}-1H-imidazo[4,5-c]pyridin-4-yl)-2-methyl-3-butyn-2-ol;GSK690693, >=98%
• CAS NO: 937174-76-0
• Molecular Formula: C₂₁H₂₇N₇O₃
• Molecular Weight: 425.48
• Product Categories: Angiogenesis and metastasis.;Inhibitors;Akt;mTOR;PI3K
• Mol File: 937174-76-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 683.8 °C at 760 mmHg
• Flash Point: 367.3 °C
• Appearance: white to beige/
• Density: 1.41
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble5mg/mL (clear solution)
• PKA: 13.11±0.29(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month.
• CAS DataBase Reference: 4-[2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-[(3S)-3-piperidinylmethoxy]-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-[(3S)-3-piperidinylmethoxy]-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol(937174-76-0)
• EPA Substance Registry System: 4-[2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-[(3S)-3-piperidinylmethoxy]-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol(937174-76-0)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 937174-76-0(Hazardous Substances Data)

Usage

Description

GSK690693 is an ATP-competitive, pan-Akt kinase inhibitor with IC50 values of 2, 13, and 9 nM for Akt1, 2, and 3, respectively. It also inhibits other members of the AGC kinase family, including AMPK, DAPK3, PAKs, PKA, PKC, PKG, and PrkX (IC50 values range from 2-81 nM). By preventing the phosphorylation of downstream Akt substrates, GSK690693 has been shown to inhibit proliferation and to induce apoptosis in various human tumor cells in vitro and in xenografts in immunocompromised mice.

Uses

Different sources of media describe the Uses of 937174-76-0 differently. You can refer to the following data:
1. GSK690693 is a pan-Akt inhibitor targeting Akt1, Akt2 and Akt3 with IC50 of 2 nM, 13 nM, and 9 nM, respectively
2. GSK690693 has been used in western blotting and immunoprecipitations.

Definition

ChEBI: A member of the class of imidazopyridines that is 4-(1-ethylimidazo[4,5-c]pyridin-4-yl)-2-methylbut-3-yn-2-ol carrying additional 2-(4-amino-1,2,5-oxadiazol-3-yl and [(3S)-piperidin-3-yl]methoxy substituents at positions 4 and 7 respectively.

Biochem/physiol Actions

GSK690693 is an ATP competitive, potent pan-AKT kinase inhibitor with IC50 values of 2, 13, and 9 nM against AKT1, 2, and 3, respectively.

References

1) Rhodes et al. (2008), Characterization of an Akt kinase inhibitor with potent pharmacodynamics and antitumor activity; Cancer Res., 68 2366 2) Crouthamel et al. (2009), Mechanism and management of AKT inhibitor-induced hyperglycemia; Clin. Cancer Res., 15 217

Upstream product

• 937174-75-9 1,1-dimethylethyl (3S)-3-({[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-4-(3-hydroxy-3-methyl-1-butyn-1-yl)-1H-imidazo[4,5-c]pyridin-7-yl]oxy}methyl)-1-piperidinecarboxylate 
• 140695-84-7 tert-butyl (3S)-3-(hydroxymethyl)piperidine-1-carboxylate 
• 937174-74-8 1,1-dimethylethyl (3S)-3-({[2-(4-amino-1,2,5-oxadiazol-3-yl)-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-7-yl]oxy}methyl)-1-piperidinecarboxylate 
• 158406-99-6 1,1-dimethylethyl (3S)-3-(bromomethyl)-1-piperidinecarboxylate 
• 842149-46-6 2-(4-amino-1,2,5-oxadiazol-3-yl)-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-7-ol 
• 842144-04-1 N-[5-romo-2-chloro-4-(ethylamino)-3-pyridinyl]-2-cyanoacetamide 
• 842144-05-2 (7-bromo-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)acetonitrile 
• 842144-03-0 5-bromo-2-chloro-N₄-ethylpyridine-3,4-diamine 
• 607371-01-7 ethyl-(3-bromo-5-nitropyridin-4-yl)amine 

Relevant articles and documents

METHODS OF USE FOR INHIBITORS OF AKT ACTIVITY

Invented is the use of 1 H-imidazo[4,5-c]pyridin-2-yl compounds in the treatment of specified cancers.