| Identification | Back Directory | [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 | [CAS]
937174-76-0 | [Synonyms]
CS-37
GSK 690693
GSK-690693 HCl
GSK690693, >=98%
GSK 690693;GSK-690693
GSK690693;GSK-690693;GSK 690693
GSK690693 GSK-690693 AKT kinase inhibitor
(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]pyr
(S)-4-(2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-(piperidin-3-ylmethoxy)-1H-imidazo[4,5-c]pyridi
(S)-4-[2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-(3-piperidylmethoxy)-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol
4-[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-[[(3S)-piperidin-3-yl]methoxy]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
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
3-Butyn-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-
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
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 ISO 9001：2015 REACH
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 | [Molecular Formula]
C21H27N7O3 | [MDL Number]
MFCD14105605 | [MOL File]
937174-76-0.mol | [Molecular Weight]
425.48 |
| Chemical Properties | Back Directory | [Boiling point ]
683.8±65.0 °C(Predicted) | [density ]
1.41 | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble5mg/mL (clear solution) | [form ]
powder | [pka]
13.11±0.29(Predicted) | [color ]
white to beige | [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. | [InChIKey]
KGPGFQWBCSZGEL-ZDUSSCGKSA-N | [SMILES]
CC(C)(O)C#CC1=NC=C(OC[C@H]2CCCNC2)C2N(CC)C(C3C(N)=NON=3)=NC1=2 |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
25 | [Safety Statements ]
45 | [RIDADR ]
UN 2811 6.1 / PGIII | [WGK Germany ]
3 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral |
| Hazard Information | Back Directory | [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.1 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).1 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.1 | [Uses]
GSK690693 is a pan-Akt inhibitor targeting Akt1, Akt2 and Akt3 with IC50 of 2 nM, 13 nM, and 9 nM, respectively | [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. | [Synthesis]
The compound of Example 1 (c) (35.0 g, 66.6 mmol) and trifluoroacetic acid (TFA, 350 mL of 20% dichloromethane solution, 808 mmol) were stirred at room temperature for 2.5 hours. Upon completion of the reaction, the reaction solution was slowly poured into a rapidly stirred mixture of water, sodium hydroxide (NaOH, 36 g, 900 mmol), ethyl acetate (200 mL) and tetrahydrofuran (THF, 1000 mL). The organic layer was separated and the aqueous layer was extracted with additional ethyl acetate/THF (1:5 v/v, 150 mL). The organic extracts were combined and washed sequentially with saturated sodium bicarbonate (NaHCO3) solution and sodium chloride (NaCl) solution, and then dried over anhydrous sodium sulfate (Na2SO4). The solvent was removed by concentration under reduced pressure and the resulting solid was recrystallized from hot ethanol (1200 mL) to give 26.3 g (93% yield) of (S)-4-(2-(4-amino-1 ,2,5-oxadiazol-3-yl)-1-ethyl-7-(piperidin-3-ylmethoxy)-1H-imidazo[4,5-c]pyridin-4-yl)-2-methylbut-3-yn-2-ol as a white crystalline solid. Mass spectrum (ES+) m/z: 426 [M+H]+. | [storage]
Store at -20°C | [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 |
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NCE Biomedical Co.,Ltd.
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4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988 |
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www.chemicalbook.com/ShowSupplierProductsList15748/0_EN.htm |
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