LDN-193189

Product Name: LDN-193189
CAS No.: 1062368-24-4
Chemical Name: LDN-193189
Synonyms: LDN193189;CS-205;DM-3189;DM 3189;LDN193189(DM3189);LDN-193189, >=98%;LDN-193189 ，S2618;LDN193189 free base;LDN-193189;LDN 193189;LDN193189 LDN193189 HCl
CBNumber: CB22512071
Molecular Formula: C25H22N6
Formula Weight: 406.48
MOL File: 1062368-24-4.mol

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LDN-193189 Property

Density: 1.33
storage temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility: H2O: soluble5mg/mL, clear (warmed)
form: powder
pka: 8.79±0.10(Predicted)
color: yellow to orange
Water Solubility: H2O: 5mg/mL, clear (warmed)
InChIKey: XHBVYDAKJHETMP-UHFFFAOYSA-N

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Safety

WGK Germany: 3
HS Code: 29339900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0559
Product name: LDN193189 hydrochloride
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $134
Updated: 2025/07/31

Sigma-Aldrich

Product number: SML0559
Product name: LDN193189 hydrochloride
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $537
Updated: 2025/07/31

Cayman Chemical

Product number: 11802
Product name: LDN-193189
Purity: ≥95%
Packaging: 1mg
Price: $35
Updated: 2024/03/01

Cayman Chemical

Product number: 11802
Product name: LDN-193189
Purity: ≥95%
Packaging: 5mg
Price: $96
Updated: 2024/03/01

Cayman Chemical

Product number: 11802
Product name: LDN-193189
Purity: ≥95%
Packaging: 10mg
Price: $140
Updated: 2024/03/01

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LDN-193189 Chemical Properties,Usage,Production

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?.

Definition

ChEBI: 4-[6-[4-(1-piperazinyl)phenyl]-3-pyrazolo[1,5-a]pyrimidinyl]quinoline is a member of pyrimidines.

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.

Synthesis

1062368-23-3

1062368-24-4

The general procedure for the synthesis of 4-(6-(4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)quinolines, using the compound (CAS: 1062368-23-3) as starting material, was as follows: 5% Pd/C catalyst and intermediate 12 (20 mg, 0.37 mmol) were dissolved in a mixture of methanol (3 mL) and dichloromethane (2 mL) solvent for degassing. Subsequently, the reaction was carried out under hydrogen atmosphere for 4 hours at room temperature. Upon completion of the reaction, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated to afford the target product 13 (13 mg, 86% yield). The product was characterized by 1H NMR (DMSO-d6) with the following chemical shifts: 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), 8.70 (d, J = 8.4 Hz, 1H), and 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).

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.

LDN-193189 Preparation Products And Raw materials

Raw materials

Preparation Products

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LDN-193189 Suppliers

China 200 India 2 United States 20 Global 222

Shanghai Boyle Chemical Co., Ltd.

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Email: sales@boylechem.com
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J & K SCIENTIFIC LTD.

Tel: 18210857532; 18210857532
Fax: 86-10-82849933
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Chembest Research Laboratories Limited

Tel: +86-21-20908456
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JinYan Chemicals(ShangHai) Co.,Ltd.

Tel: 13817811078
Fax: 86-021-50426522,50426273
Email: sales@jingyan-chemical.com
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Shangchem Co., Ltd.

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Jinan Trio PharmaTech Co., Ltd.

Tel: 0531-88811783
Fax: +86 (531) 55696010 QQ 1762738062
Email: sales@trio-pharmatech.com
Country: China
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NCE Biomedical Co.,Ltd.

Tel: 4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
Fax: +86-27-87599188
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Haoyuan Chemexpress Co., Ltd.

Tel: 021-58950125
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Shanghai Aladdin Bio-Chem Technology Co.,LTD

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Moltt Biocem Co., Ltd.

Tel: +86-21-38682181 15900741819
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View Lastest Price from LDN-193189 manufacturers

Career Henan Chemical Co

Product: 6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine 1062368-24-4
Price: US $9.80/KG
Min. Order: 1g
Purity: ≥99%
Supply Ability: 100kg
Release date: 2020-01-08

1062368-24-4, LDN-193189Related Search:

LDN-212320 LDN-193189 HCl 2,5-Dimethoxyaniline tert-Butyl 1-piperazinecarboxylate Piperazine LDN-214117 Y27632 (hydrochloride) 1,9-Pyrazoloanthrone SB 431542 LY2109761 ICG-001 LDN212854 Ldn193189

LDN193189 LDN193189 HCl

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

LDN-193189;LDN 193189;DM-3189;DM 3189

LDN-193189;LDN 193189

CS-205

LDN193189 free base

LDN193189(DM3189)

LDN193189

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

DM 3189

DM-3189

6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyriMidine LDN 193189(DM3189)

4-{6-[4-(piperazin-1-yl)phenyl]pyrazolo[

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

4-[6-[4-(1-Piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-quinoline hydrochloride

LDN-193189, >=98%

LDN-193189, 98%, a selective BMP signaling inhibitor

Quinoline, 4-[6-[4-(1-piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-

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

LDN-193189 ，S2618

LDN-193189（1062368-24-4）

1062368-24-4

C25H22N6

Smad

TGF-beta

Inhibitors

TGF-beta/Smad