ChemicalBook--->CAS DataBase List--->1062368-24-4

1062368-24-4

1062368-24-4 Structure

1062368-24-4 Structure
IdentificationBack Directory
[Name]

6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine
[CAS]

1062368-24-4
[Synonyms]

CS-205
DM 3189
DM-3189
LDN193189
LDN-193189, >=98%
LDN193189(DM3189)
LDN193189 free base
LDN-193189;LDN 193189
LDN193189 LDN193189 HCl
LDN-193189;LDN 193189;DM-3189;DM 3189
4-{6-[4-(piperazin-1-yl)phenyl]pyrazolo[
LDN-193189, 98%, a selective BMP signaling inhibitor
4-[6-[4-(1-Piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]quinoline
4-(6-(4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)quinoline
Quinoline, 4-[6-[4-(1-piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-
4-[6-[4-(1-Piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-quinoline hydrochloride
6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine USP/EP/BP
6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyriMidine LDN 193189(DM3189)
4-[6-[4-(1-Piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]quinoline LDN 193189
LDN 193189 4-[6-[4-(1-Piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]quinoline
[Molecular Formula]

C24H25N5O
[MDL Number]

MFCD17392570
[MOL File]

1062368-24-4.mol
[Molecular Weight]

399.488
Chemical PropertiesBack Directory
[density ]

1.33
[storage temp. ]

?20°C
[solubility ]

H2O: soluble5mg/mL, clear (warmed)
[form ]

powder
[pka]

8.79±0.10(Predicted)
[color ]

yellow to orange
[InChIKey]

XHBVYDAKJHETMP-UHFFFAOYSA-N
Safety DataBack Directory
[WGK Germany ]

3
[HS Code ]

29339900
Hazard InformationBack Directory
[Description]

Normal development and tissue repair are controlled in part by SMADs, a family of intracellular proteins that are activated by signaling via serine/threonine kinase receptors of the TGF-β superfamily. LDN-193189 inhibits SMAD1/5/8 phosphorylation by the bone morphogenetic protein (BMP) type I receptors, which are known as activin receptor-like kinases (ALKs), with an IC50 value of 4.9 nM. In in vitro kinase assays, it shows specificity for ALK1, 2, 3, and 6 (IC50s = 0.8, 0.8, 5.3, and 16.7 nM, respectively) over ALK4 and 5 (IC50s = 101 and 350 nM, respectively). LDN-193189 has been used to inhibit BMP type I receptor activity to study the pathogenesis of fibrodysplasia ossificans progressive, a congenital hyperossification disorder, and to examine the role of osteogenesis in prostate tumor metastases in bone.
[Uses]

4-(6-(4-(Piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)quinoline, is a selective inhibitor of bone morphogenetic protein (BMP) pathway, useful in the treatment of diseases. Potent BMP Inhibitor?, Promotes hPSC Neural Induction?.
[Biochem/physiol Actions]

Although LDN193189 is a structural analog of dorsomorphin, these two drugs are found to establish different cellular responses. In vitro analysis reveals that LDN193189 inhibits a number of intracellular kinases such as, mitogen activated protein kinase 14 and 8 ( p38and c-Jun N-terminal kinase respectively), as well as those associated with AKT (serine/threonine kinase) and mTOR (mammalian target of rapamycin) signaling mechanisms. LDN193189 is known to elevate the levels hemoglobin and thus helps to prevent the onset of anemia of inflammation.
[References]

[1] yu pb, deng dy, lai cs, hong cc, cuny gd, bouxsein ml, hong dw, mcmanus pm, katagiri t, sachidanandan c, kamiya n, fukuda t, mishina y, peterson rt, bloch kd. bmp type i receptor inhibition reduces heterotopic [corrected] ossification. nat med. 2008 dec;14(12):1363-9.
[2] boergermann jh1, kopf j, yu pb, knaus p. dorsomorphin and ldn-193189 inhibit bmp-mediated smad, p38 and akt signalling in c2c12 cells. int j biochem cell biol. 2010 nov;42(11):1802-7.
[3] helbing t1, herold em, hornstein a, wintrich s, heinke j, grundmann s, patterson c, bode c, moser m. inhibition of bmp activity protects epithelial barrier function in lung injury. j pathol. 2013 sep;231(1):105-16. doi: 10.1002/path.4215. epub 2013 jul 10.
Spectrum DetailBack Directory
[Spectrum Detail]

LDN-193189(1062368-24-4)1HNMR
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