6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE
- Product Name
- 6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE
- CAS No.
- 866405-64-3
- Chemical Name
- 6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE
- Synonyms
- Dorsomorphin;COMPOUND C;BML-275;DORSOMORPHIN 2HCL;BML-275HCL;Dorsomorphin dihydrochloride;CS-1075;AMPK INHIBITOR;Dorsomorphin, 98%+;dorsoMorphin (BML-275)
- CBNumber
- CB8786803
- Molecular Formula
- C24H25N5O
- Formula Weight
- 399.49
- MOL File
- 866405-64-3.mol
6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE Property
- Melting point:
- >228°C(dec.)
- Density
- 1.25±0.1 g/cm3(Predicted)
- storage temp.
- 2-8°C
- solubility
- DMSO: >2mg/mL (warmed)
- pka
- 8.53±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.
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- 171260
- Product name
- AMPK Inhibitor, Compound C
- Packaging
- 1mg
- Price
- $130
- Updated
- 2024/03/01
- Product number
- 171260
- Product name
- AMPK Inhibitor, Compound C
- Packaging
- 5mg
- Price
- $373
- Updated
- 2024/03/01
- Product number
- D5394
- Product name
- Dorsomorphin
- Purity
- >97.0%(HPLC)
- Packaging
- 10mg
- Price
- $211
- Updated
- 2024/03/01
- Product number
- D5394
- Product name
- Dorsomorphin
- Purity
- >97.0%(HPLC)
- Packaging
- 50mg
- Price
- $634
- Updated
- 2024/03/01
- Product number
- 11967
- Product name
- Dorsomorphin
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $57
- Updated
- 2024/03/01
6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE Chemical Properties,Usage,Production
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
Dorsomorphin 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
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
6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE Preparation Products And Raw materials
Raw materials
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View Lastest Price from 6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE manufacturers
- Product
- 6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE 866405-64-3
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 25kg
- Release date
- 2019-07-11