6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE

6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE
  • CAS No.:866405-64-3

Important Notice

  1. This product is a chemical product/pharmaceutical intermediate. It is not a drug, an active pharmaceutical ingredient (API), or a pharmaceutical-grade material. It has not been granted a drug approval number or a Chemical Drug Substance Approval Notice, has not passed drug-related review and approval, and is not manufactured, tested, or released in accordance with pharmaceutical GMP.
  2. This product is intended solely for non-clinical research, process development, quality studies, further chemical processing, or chemical synthesis. It must not be used in drug-product manufacturing, clinical trials, clinical diagnosis, or administration to humans or animals, or be sold, used as an input, submitted for regulatory filing, or released as an API or pharmaceutical material.
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6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE Basic information
Product Name:6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE
Synonyms:AMPK INHIBITOR;6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE;COMPOUND C;AMPK Inhibitor, Compound C, Dorsomorphin;InSolution AMPK Inhibitor, Compound C - CAS 866405-64-3 - Calbiochem;InSolution AMPK Inhibitor, Compound C2HCl - CAS 866405-64-3 - Calbiochem;AMPK Inhibitor, Compound C - CAS 866405-64-3 - Calbiochem;CS-1075
CAS:866405-64-3
MF:C24H25N5O
MW:399.49
EINECS:
Product Categories:Inhibitors
Mol File:866405-64-3.mol
6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE Chemical Properties
Melting point >228°C(dec.)
density 1.25±0.1 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO: >2mg/mL (warmed)
pka8.53±0.10(Predicted)
form powder
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.
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22
Safety Statements 36/37
WGK Germany 3
HS Code 2933599590
MSDS Information
6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE Usage And Synthesis
DescriptionDorsomorphin (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
UsesDorsomorphin has been used:
  • as an inhibitor of adenosine monophosphate-activated protein kinase (AMPK) to find the effects of trans-resveratrol on lipid mobilization in 3T3-L1 (a murine cell line of adipocytes) cells
  • as an AMPK inhibitor, to indicate the involvement of AMPK/mTOR (mammalian target of rapamycin) pathway in LRG (liraglutide) -induced autophagy
  • in the induction step, employed in in vitro differentiation of Friedreich′s ataxia (FRDA) and induced pluripotent stem cells (iPSCs) to neurospheres and neurons using ES (embryonic stem cell) media
UsesA potent inhibitor of AMPK and fatty acid biosynthesis.
DefinitionChEBI: 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 DescriptionA 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 ActivityPotent 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 ActionsTarget IC50: 25.1, 148, and 234.6 nM, against KDR/VEGFR2, ALK2/BMPR-I, AMPK kinase activity, respectively
References1) 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
6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE Preparation Products And Raw materials

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