4-[6-[4-(1-Methylethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-quinoline Chemical Properties

Melting point:

178 °C

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: soluble5mg/mL, clear (warmed)

pka

3.34±0.46(Predicted)

form 

powder

color 

light yellow to orange

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

WGK Germany 

3

HS Code 

2933.49.7000

4-[6-[4-(1-Methylethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-quinoline Usage And Synthesis

Description

Bone morphogenetic proteins (BMP) are secreted signaling proteins, many of which are involved in various developmental processes, in addition to bone formation. DMH1 is an analog of the non-selective BMP receptor inhibitor dorsomorphin that potently inhibits the kinase activity of activin receptor-like kinase 2 (ALK2; IC₅₀ = 13-108 nM). It is much less effective at ALK4, ALK5, AMPK, KDR (VEGFR2) or PDGFRβ, although it inhibits ALK1 and ALK3 at nanomolar concentrations. DMH1 is effective in vivo, as it disrupts dorsoventral development in zebrafish. It also affects stem cell development, increasing cardiomyocyte progenitors and promoting neurogenesis. DMH1 inhibits the growth of lung cancer cells, reducing tumor growth in a xenograft mouse model.

Uses

DMH1 has been used for bone morphogenetic protein (BMP) inhibition. It has also been used to block vascular endothelial growth factor (VEGF) signaling.

Uses

DMH 1 is an inhibitor that exclusively targets the bone morphogenetic protein (BMP) but not the vascular endothelial growth factor (VEGF) pathway. DMH 1 promotes neurogenesis of human-induced pluripotent stem cells (hiPSCs)

Definition

ChEBI: DMH1 is a pyrazolopyrimidine that is pyrazolo[1,5-a]pyrimidine bearing quinolin-4-yl and 4-isopropyloxyphenyl substituents at positions 3 and 6 respectively. It has a role as a protein kinase inhibitor, a bone morphogenetic protein receptor antagonist and an antineoplastic agent. It is a member of quinolines, a pyrazolopyrimidine and an aromatic ether.

General Description

DMH1 stimulates neurogenesis of human-induced pluripotent stem cells (hiPSCs) and suppresses the growth and metastasis of lung cancer. It blocks cellular autophagy responses.

Biochem/physiol Actions

DMH1 is a highly selective Bone morphogenetic protein (BMP) inhibitor. DMH1 is a dorsomorphin analogue that exclusively targets the BMP but not the VEGF pathway.

storage

+4°C

References

[1] hao j, ho j n, lewis j a, et al. in vivo structure- activity relationship study of dorsomorphin analogues identifies selective vegf and bmp inhibitors. acs chemical biology, 2010, 5(2): 245-253.
[2] hao j, lee r, chang a, et al. dmh1, a small molecule inhibitor of bmp type i receptors, suppresses growth and invasion of lung cancer. plos one, 2014, 9(3): e90748.

4-[6-[4-(1-Methylethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-quinoline(1206711-16-1)Related Product Information

• Y27632 (hydrochloride)
• BML-275
• SB 431542
• (2S)-1-[3-Ethyl-7-[[(1-oxido-3-pyridinyl)methyl]amino]pyrazolo[1,5-a]pyrimidin-5-yl]-2-piperidineethanol
• Rapamycin
• LY 2157299