| Identification | Back Directory | [Name]
LDN-193189 HCl | [CAS]
1062368-62-0 | [Synonyms]
CS-1451
1062368-62-0
LDN-193189 HCl
LDN-193189 4HCl
LDN-193189 HCl USP/EP/BP
LDN193189 (Hydrochloride)
LDN-193189 HCL;LDN 193189 HCL
4-(6-(4-(Piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyriMidin-3-yl)quinoline HCl
LDN193189 hydrochloride, 98%, a selective BMP type I receptor kinases inhibitor
LDN-193189 HCL;LDN 193189 HCL;LDN 193189 HYDROCHLORIDE;LDN-193189 HYDROCHLORIDE
4-(6-(4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)quinoline hydrochloride
4-[6-[4-(1-Piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]quinoline hydrochloride (1:1) | [Molecular Formula]
C25H23ClN6 | [MDL Number]
MFCD17392570 | [MOL File]
1062368-62-0.mol | [Molecular Weight]
442.943 |
| Chemical Properties | Back Directory | [Melting point ]
>240°C (dec.) | [storage temp. ]
Inert atmosphere,Store in freezer, under -20°C | [solubility ]
Methanol (Slightly), DMSO (Very Slightly, Heated) | [form ]
Solid | [color ]
Dark Orange | [CAS DataBase Reference]
1062368-62-0 |
| Hazard Information | Back Directory | [Uses]
LDN-193189 HCl 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.
| [Biological Activity]
ldn193189 is a selective transcriptional activity morphogenetic protein (bmp) type i receptors inhibitor. it inhibits activin receptor-like kinase-2 (alk2) and alk3 with ic50 values of 5 nm and 30 nm, respectively [1].ldn193189 has been showed to inhibit bmp induced phosphorylation of smad signaling (smad1/5/8) and non-smad signaling including p38 and akt in c2c12 cells [2].pharmacological inhibition of bmp by ldn193189 has shown to prevent down-regulation of e-cadherin in response to bmp2 both in bronchial epithelial (beas2b) cells and in c57bl/6 mice. ldn193189 also inhibits the bmp-induced reduction of epithelial permeability at cellular level [3]. | [Synthesis]
Compound 18a (640 mg, 1.26 mmol) was taken as raw material and dissolved in methanol (10 mL) and 1,4-dioxane solution (6.3 mL) in 4M HCl was added. The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, the mixture was concentrated to dryness. The resulting residue was washed with a small amount of methanol to afford the target product 13-HCl (550 mg, 98% yield) as a yellow solid. The product was characterized by 1H NMR (DMSO-d6): δ 9.75 (d, J = 2.2 Hz, 1H), 9.40 (br.s, 1H), 9.29 (d, J = 5.9 Hz, 1H), 9.28 (d, J = 2.2 Hz, 1H), 9.07 (s, 1H), 8.70 (d, J = 8.4 Hz, 1H), 8.51 (d, J = 5.9 Hz, 1H), 8.47 (d, J = 8.4 Hz, 1H), 8.21 (t, J = 7.6 Hz, 1H), 7.99 (t, J = 7.6 Hz, 1H), 7.88 (d, J = 8.8 Hz, 2H), 7.19 (d, J = 8.8 Hz, 2H), 3.51-3.58 (m, 4H), 3.20- 3.30 (m, 4H). The molecular ion peak m/z was determined to be 407.1979 by high-resolution mass spectrometry (HRMS), which is consistent with the calculated value of 407.1979 for the theoretical value C25H23N6 (MH+). | [storage]
Store at -20°C | [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. |
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