Dorsomorphin

Base Information

• Chemical Name: Dorsomorphin
• CAS No.: 866405-64-3
• Molecular Formula: C₂₄H₂₅N₅O
• Molecular Weight: 399.495
• Hs Code.: 2933990090
• European Community (EC) Number: 635-949-5
• UNII: 10K52CIC1Z
• ChEMBL ID: CHEMBL478629
• DSSTox Substance ID: DTXSID401006988
• Metabolomics Workbench ID: 151722
• Nikkaji Number: J2.625.625I
• Pharos Ligand ID: YS5RSZQDF5R3
• Wikidata: Q27077101
• Mol file: 866405-64-3.mol

Synonyms:(6-(4-(2-piperidin-1-ylethoxy)phenyl))-3-pyridin-4-ylpyrazolo(1,5-a)pyrimidine;4-(6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)pyrazolo(1,5-a)pyrimidin-3-yl)pyridine;6-(4-(2-(1-Piperidinyl)ethoxy)phenyl)-3-(4-pyridinyl)pyrazolo(1,5-a)pyrimidine;AMPK inhibitor, compound C;compound C dorsomorphin;dorsomorphin

Chemical Property of Dorsomorphin

Chemical Property:

• Refractive Index: 1.67
• PKA: 8.53±0.10(Predicted)
• PSA: 55.55000
• Density: 1.255 g/cm³
• LogP: 4.26090
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >2mg/mL (warmed)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 399.20591044
• Heavy Atom Count: 30
• Complexity: 514

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dorsomorphin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(CC1)CCOC2=CC=C(C=C2)C3=CN4C(=C(C=N4)C5=CC=NC=C5)N=C3
• 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) cellsas an AMPK inhibitor, to indicate the involvement of AMPK/mTOR (mammalian target of rapamycin) pathway in LRG (liraglutide) -induced autophagyin 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 A potent inhibitor of AMPK and fatty acid biosynthesis.

Technology Process of Dorsomorphin

There total 9 articles about Dorsomorphin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

N-chloroethylpiperidine hydrochloride (2008-75-5) + 6-(4-hydroxyphenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine (515880-87-2) → dorsomorphin (866405-64-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 - 45 ℃; Inert atmosphere;

Reference yield:

pyridin-4-ylacetonitrile (13121-99-8) → dorsomorphin (866405-64-3)

Guidance literature:

Multi-step reaction with 5 steps

1: N,N-dimethyl-formamide / 5 h / 110 °C

2: hydrazine dihydrochloride; hydrazine hydrate / ethanol; water / 5 h / 110 °C

3: acetic acid / ethanol / 6 h / 110 °C

4: acetic acid; hydrogen bromide / 0.17 h / 130 °C

5: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 - 45 °C / Inert atmosphere

With hydrazine dihydrochloride; hydrazine hydrate; hydrogen bromide; sodium hydride; acetic acid; In ethanol; water; N,N-dimethyl-formamide; mineral oil;

Reference yield:

4-(Chloromethyl)pyridine (10445-91-7) → dorsomorphin (866405-64-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1-methyl-pyrrolidin-2-one / 3 h / 130 °C / Inert atmosphere

2: N,N-dimethyl-formamide / 5 h / 110 °C

3: hydrazine dihydrochloride; hydrazine hydrate / ethanol; water / 5 h / 110 °C

4: acetic acid / ethanol / 6 h / 110 °C

5: acetic acid; hydrogen bromide / 0.17 h / 130 °C

6: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 - 45 °C / Inert atmosphere

With hydrazine dihydrochloride; hydrazine hydrate; hydrogen bromide; sodium hydride; acetic acid; In 1-methyl-pyrrolidin-2-one; ethanol; water; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

pyridin-4-ylacetonitrile

4-(Chloromethyl)pyridine

3-(dimethylamino)-2-(4-pyridyl)prop-2-enenitrile

5-amino-4-(pyridin-4-yl)-1H-pyrazole

Refernces