866405-64-3

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;BML-275;Dorsomorphin;6-[4-[2-(1-Piperidinyl)ethoxy]phenyl]-3-(4-pyridinyl)-pyrazolo[1,5-a]pyrimidinedihydrochloride;Dorsomorphin dihydrochloride
• CAS NO: 866405-64-3
• Molecular Formula: C24H25N5O
• Molecular Weight: 399.4882
• Product Categories: Inhibitors
• Mol File: 866405-64-3.mol
• Article Data: 1

Chemical Properties

• Appearance: white to beige/
• Density: 1.255 g/cm³
• Refractive Index: 1.67
• Storage Temp.: 2-8°C
• Solubility: DMSO: >2mg/mL (warmed)
• PKA: 8.53±0.10(Predicted)
• 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.
• CAS DataBase Reference: 6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE(866405-64-3)
• EPA Substance Registry System: 6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE(866405-64-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 866405-64-3(Hazardous Substances Data)

Usage

Description

6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE, also known as Dorsomorphin, is a cell-permeable pyrazolopyrimidine compound that acts as a potent, selective, and ATP-competitive inhibitor of AMP-activated protein kinase (AMPK) and a selective inhibitor of bone morphogenetic protein (BMP) signaling. It has been shown to block both BMP pathway-dependent dorsoventral development and VEGF signaling-dependent intersomitic vessel formation in zebrafish embryo in vivo.

Uses

Used in Research Applications:
6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE is used as an AMPK inhibitor for studying AMPK-dependent cellular events in vitro and physiological responses in animals in vivo.
Used in Pharmaceutical Industry:
6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE is used as a potent inhibitor of AMPK and fatty acid biosynthesis, and as an inhibitor of bone morphogenetic protein (BMP) type I receptors (ALK2, ALK3, and ALK6).
Used in Cell Biology Research:
6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE is used as an inducer of autophagy in cancer cell lines via a mechanism independent of AMPK inhibition.
Used in Developmental Biology:
6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE is used in the induction step of in vitro differentiation of Friedreich's ataxia (FRDA) and induced pluripotent stem cells (iPSCs) to neurospheres and neurons using embryonic stem cell (ES) media.
Used in Cardiovascular Research:
6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE is used to promote cardiomyogenesis in mouse embryonic stem cells (ESCs) in vitro.

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

InChI:InChI=1/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

Upstream product

• 13121-99-8 pyridin-4-ylacetonitrile 
• 10445-91-7 4-(Chloromethyl)pyridine 
• 103851-89-4 3-(dimethylamino)-2-(4-pyridyl)prop-2-enenitrile 
• 216661-87-9 5-amino-4-(pyridin-4-yl)-1H-pyrazole 
• 100-09-4 4-methoxybenzoic acid 
• 65192-28-1 2-(4-methoxyphenyl)malondialdehyde 
• 216661-58-4 3-(pyridin-4-yl)-6-(4-methoxyphenyl)-pyrazolo(1,5-A)pyrimidine 
• 2008-75-5 N-chloroethylpiperidine hydrochloride 
• 515880-87-2 6-(4-hydroxyphenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine 

Relevant articles and documents

Inhibitor of heat shock factor 1, and preparation method and application of inhibitor

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