| Identification | Back Directory | [Name]
6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE | [CAS]
866405-64-3 | [Synonyms]
CS-1075
BML-275
COMPOUND C
BML-275HCL
Dorsomorphin
AMPK INHIBITOR
DORSOMORPHIN 2HCL
Dorsomorphin, 98%+
BML-275(Dorsomorphin )
dorsoMorphin (BML-275)
DorsoMorphin (CoMpound C)
AMPK Inhibitor, Compound C
Dorsomorphin dihydrochloride
DorsoMorphin, Free Base, >99%
DORSOMORPHIN(COMPOUND C; BML-275)
InSolution? AMPK Inhibitor, Compound C
Dorsomorphin (Compound C) (DMSO solution)
InSolution? AMPK Inhibitor, Compound C?2HCl
AMPK Inhibitor, Compound C, Dorsomorphin
AMPK Inhibitor, Compound C - CAS 866405-64-3 - Calbiochem
InSolution AMPK Inhibitor, Compound C - CAS 866405-64-3 - Calbiochem
InSolution AMPK Inhibitor, Compound C2HCl - CAS 866405-64-3 - Calbiochem
6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE
6-[4-[2-(1-piperidinyl)ethoxy]phenyl]-3-(4-pyridinyl)-pyrazolo[1,5-a]pyrimidine
6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(yridine-4-yl)pyrazolo[1,5-a]pyrimidine
6-(4-(2-(Piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrrazolo[1,5-a]pyrimidine
Pyrazolo[1,5-a]pyriMidine, 6-[4-[2-(1-piperidinyl)ethoxy]phenyl]-3-(4-pyridinyl)-
6-[4-[2-(1-Piperidinyl)ethoxy]phenyl]-3-(4-pyridinyl)-pyrazolo[1,5-a]pyrimidinedihydrochloride | [Molecular Formula]
C24H25N5O | [MDL Number]
MFCD08705402 | [MOL File]
866405-64-3.mol | [Molecular Weight]
399.488 |
| Chemical Properties | Back Directory | [Melting point ]
>228°C(dec.) | [density ]
1.25±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: >2mg/mL (warmed) | [form ]
powder | [pka]
8.53±0.10(Predicted) | [color ]
white to beige | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. | [InChI]
InChI=1S/C24H25N5O/c1-2-12-28(13-3-1)14-15-30-22-6-4-19(5-7-22)21-16-26-24-23(17-27-29(24)18-21)20-8-10-25-11-9-20/h4-11,16-18H,1-3,12-15H2 | [InChIKey]
XHBVYDAKJHETMP-UHFFFAOYSA-N | [SMILES]
C12=C(C3C=CN=CC=3)C=NN1C=C(C1=CC=C(OCCN3CCCCC3)C=C1)C=N2 |
| Hazard Information | Back Directory | [Description]
Dorsomorphin (866405-64-3) is a potent, selective and ATP-competitive inhibitor of AMP-activated protein kinase (AMPK) (Ki = 109 nM).1 It displays no significant inhibition of ZAPK, SYK, PKCT, PKA and JAK3. It inhibits bone morphogenetic protein (BMP) type I receptors (ALK2, ALK3 and ALK6).2 Dorsomorphin has been shown to promote cardiomyogenesis in mouse embryonic stem cells (ESCs) in vitro.3 Dorsomorphin also induces autophagy in cancer cell lines via a mechanism independent of AMPK inhibition.4 | [Uses]
A potent inhibitor of AMPK and fatty acid biosynthesis. | [Definition]
ChEBI: A pyrazolopyrimidine that is pyrazolo[1,5-a]pyrimidine which is substituted at positions 3 and 6 by pyridin-4-yl and p-[2-(piperidin-1-yl)ethoxy]phenyl groups, respectively. It is a potent, selective, reversible, and ATP-competiti
e inhibitor of AMPK (AMP-activated protein kinase, EC 2.7.11.31) and a selective inhibitor of bone morphogenetic protein (BMP) signaling. | [General Description]
A cell-permeable pyrrazolopyrimidine compound that inhibits against KDR/VEGFR2, ALK2/BMPR-I, AMPK kinase activity (IC50 = 25.1, 148, and 234.6 nM, respectively), while exhibiting much reduced or little effect toward ALK5/TGFβR-I, ZAPK, Syk, PKCθ, PKA, or JAK3. Shown to block both BMP pathway-dependent dorsoventral development (EC100 = 2.5 μM) and VEGF signaling-dependent intersomitic vessel formation (EC50 = 5 μM) in zebrafish embryo in vivo. Commonly used in combination with AMPK activators AICAR (Cat. No. 123040) and/or Metformin (Cat. No. 317240) for studying AMPK-dependent cellular events in vitro and physiological responses in animals in vivo. | [Biological Activity]
Potent and selective inhibitor of AMP-activated protein kinase (AMPK) (K i = 109 nM). Displays no significant activity on several structurally related kinases including ZAPK, SYK, PKC θ , PKA and JAK3. Inhibits AMPK activation induced by AICAR and metformin. Also inhibits bone morphogenic protein (BMP) type I receptors (ALK2, ALK3 and ALK6). Promotes cardiomyogenesis in mouse embryonic stem cells (ESCs) in vitro . | [Biochem/physiol Actions]
Target IC50: 25.1, 148, and 234.6 nM, against KDR/VEGFR2, ALK2/BMPR-I, AMPK kinase activity, respectively | [References]
1) Zhou et al. (2001) Role of AMP-activated protein kinase in mechanism of metformin action; J. Clin. Invest. 108 1167
2) Yu et al. (2008) Dorsomorphin inhibits BMP signals required for embryogenesis and iron metabolism; Nat. Chem. Biol. 4 33
3) Hao et al. (2008) Dorsomorphin, a selective small molecule inhibitor of BMP signaling, promotes cardiomyogenesis in embryonic stem cells; PLoS ONE, 3 2904
4) Vucicevic et al. (2011) Compound C induces protective autophagy in cancer cells through AMPK inhibition-independent blockade of Akt/mTOR pathway; Autophagy 7 40 |
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