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1062368-24-4

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  • Factory Price API 99% 6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine 1062368-24-4 GMP Manufacturer

    Cas No: 1062368-24-4

  • USD $ 0.1-0.1 / Gram

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  • Xi'an Xszo Chem Co., Ltd.
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1062368-24-4 Usage

Description

6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine is a complex organic compound with a unique molecular structure. It is characterized by its pyrazolo[1,5-a]pyrimidine core, which is fused with a phenyl ring at the 6th position and a pyridin-4-yl group at the 3rd position. The molecule also features a piperidin-1-yl ethoxy group attached to the phenyl ring, which may contribute to its biological activity and potential applications.

Uses

1. Used in Pharmaceutical Industry:
6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine is used as a potent inhibitor for the bone morphogenetic protein (BMP) pathway. Its application is based on its ability to selectively inhibit the BMP pathway, which plays a crucial role in normal development and tissue repair. By targeting the SMAD1/5/8 phosphorylation mediated by the BMP type I receptors (ALKs), this compound can be useful in the treatment of various diseases associated with the dysregulation of the BMP pathway.
2. Used in Research Applications:
6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine is also used as a research tool to study the pathogenesis of fibrodysplasia ossificans progressive, a congenital hyperossification disorder. By inhibiting the BMP type I receptor activity, this compound can help researchers understand the underlying mechanisms of the disease and potentially identify new therapeutic targets.
3. Used in Neural Induction:
6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine has been shown to promote hPSC (human pluripotent stem cells) neural induction. This application is significant for advancing stem cell research and regenerative medicine, as it can facilitate the generation of specific cell types, such as neurons, from stem cells for therapeutic purposes or for studying neurological disorders in vitro.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 1062368-24-4 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,0,6,2,3,6 and 8 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1062368-24:
(9*1)+(8*0)+(7*6)+(6*2)+(5*3)+(4*6)+(3*8)+(2*2)+(1*4)=134
134 % 10 = 4
So 1062368-24-4 is a valid CAS Registry Number.

1062368-24-4 Well-known Company Product Price

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  • Sigma

  • (SML0559)  LDN193189 hydrochloride  ≥98% (HPLC)

  • 1062368-24-4

  • SML0559-5MG

  • 1,123.20CNY

  • Detail
  • Sigma

  • (SML0559)  LDN193189 hydrochloride  ≥98% (HPLC)

  • 1062368-24-4

  • SML0559-25MG

  • 4,533.75CNY

  • Detail

1062368-24-4Synthetic route

C33H28N6O2
1062368-23-3

C33H28N6O2

LDN-193189
1062368-24-4

LDN-193189

Conditions
ConditionsYield
With 5% Pd/C; hydrogen In methanol; dichloromethane at 20℃; under 760.051 Torr; for 4h;86%
With hydrogen; 5%-palladium/activated carbon In methanol; dichloromethane at 20℃; under 760.051 Torr; for 4h;86%
quinoline-4-carboxaldehyde
4363-93-3

quinoline-4-carboxaldehyde

LDN-193189
1062368-24-4

LDN-193189

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: methanol; sodium tetrahydroborate / 1.33 h / 0 - 20 °C
2.1: thionyl chloride / dichloromethane / 2.33 h / 0 - 20 °C
2.2: pH > 7 / Saturated solution
3.1: N,N-dimethyl-formamide / 20 - 80 °C
4.1: 6 h / 120 °C
5.1: hydrazine monohydrobromide / ethanol; water / 5 h / 110 °C
5.2: Saturated solution
6.1: acetic acid / ethanol / 0.08 h / 170 °C / Microwave irradiation
7.1: potassium tert-butylate / tris-(dibenzylideneacetone)dipalladium(0); johnphos / 1,1-dichloroethane / 20 h / 100 °C / Inert atmosphere
8.1: hydrogen / 5%-palladium/activated carbon / methanol; dichloromethane / 4 h / 20 °C / 760.05 Torr
View Scheme
4-quinolylmethanol
6281-32-9

4-quinolylmethanol

LDN-193189
1062368-24-4

LDN-193189

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: thionyl chloride / dichloromethane / 2.33 h / 0 - 20 °C
1.2: pH > 7 / Saturated solution
2.1: N,N-dimethyl-formamide / 20 - 80 °C
3.1: 6 h / 120 °C
4.1: hydrazine monohydrobromide / ethanol; water / 5 h / 110 °C
4.2: Saturated solution
5.1: acetic acid / ethanol / 0.08 h / 170 °C / Microwave irradiation
6.1: potassium tert-butylate / tris-(dibenzylideneacetone)dipalladium(0); johnphos / 1,1-dichloroethane / 20 h / 100 °C / Inert atmosphere
7.1: hydrogen / 5%-palladium/activated carbon / methanol; dichloromethane / 4 h / 20 °C / 760.05 Torr
View Scheme
4-(chloromethyl)quinoline
5632-17-7

4-(chloromethyl)quinoline

LDN-193189
1062368-24-4

LDN-193189

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: N,N-dimethyl-formamide / 20 - 80 °C
2.1: 6 h / 120 °C
3.1: hydrazine monohydrobromide / ethanol; water / 5 h / 110 °C
3.2: Saturated solution
4.1: acetic acid / ethanol / 0.08 h / 170 °C / Microwave irradiation
5.1: potassium tert-butylate / tris-(dibenzylideneacetone)dipalladium(0); johnphos / 1,1-dichloroethane / 20 h / 100 °C / Inert atmosphere
6.1: hydrogen / 5%-palladium/activated carbon / methanol; dichloromethane / 4 h / 20 °C / 760.05 Torr
View Scheme
2-(quinolin-4-yl)acetonitrile
14003-46-4

2-(quinolin-4-yl)acetonitrile

LDN-193189
1062368-24-4

LDN-193189

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 6 h / 120 °C
2.1: hydrazine monohydrobromide / ethanol; water / 5 h / 110 °C
2.2: Saturated solution
3.1: acetic acid / ethanol / 0.08 h / 170 °C / Microwave irradiation
4.1: potassium tert-butylate / tris-(dibenzylideneacetone)dipalladium(0); johnphos / 1,1-dichloroethane / 20 h / 100 °C / Inert atmosphere
5.1: hydrogen / 5%-palladium/activated carbon / methanol; dichloromethane / 4 h / 20 °C / 760.05 Torr
View Scheme
C14H13N3
1062368-20-0

C14H13N3

LDN-193189
1062368-24-4

LDN-193189

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrazine monohydrobromide / ethanol; water / 5 h / 110 °C
1.2: Saturated solution
2.1: acetic acid / ethanol / 0.08 h / 170 °C / Microwave irradiation
3.1: potassium tert-butylate / tris-(dibenzylideneacetone)dipalladium(0); johnphos / 1,1-dichloroethane / 20 h / 100 °C / Inert atmosphere
4.1: hydrogen / 5%-palladium/activated carbon / methanol; dichloromethane / 4 h / 20 °C / 760.05 Torr
View Scheme
4-quinolin-4-yl-2H-pyrazol-3-ylamine
1062368-21-1

4-quinolin-4-yl-2H-pyrazol-3-ylamine

LDN-193189
1062368-24-4

LDN-193189

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid / ethanol / 0.08 h / 170 °C / Microwave irradiation
2: potassium tert-butylate / tris-(dibenzylideneacetone)dipalladium(0); johnphos / 1,1-dichloroethane / 20 h / 100 °C / Inert atmosphere
3: hydrogen / 5%-palladium/activated carbon / methanol; dichloromethane / 4 h / 20 °C / 760.05 Torr
View Scheme
C21H13BrN4
1062368-22-2

C21H13BrN4

LDN-193189
1062368-24-4

LDN-193189

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium tert-butylate / tris-(dibenzylideneacetone)dipalladium(0); johnphos / 1,1-dichloroethane / 20 h / 100 °C / Inert atmosphere
2: hydrogen / 5%-palladium/activated carbon / methanol; dichloromethane / 4 h / 20 °C / 760.05 Torr
View Scheme

1062368-24-4Downstream Products

1062368-24-4Relevant articles and documents

INHIBITORS OF THE BMP SIGNALING PATHWAY

-

, (2009/10/22)

The present invention provides small molecule inhibitors of BMP signaling. These compounds may be used to modulate cell growth, differentiation, proliferation, and apoptosis, and thus may be useful for treating diseases or conditions associated with BMP signaling, including inflammation, cardiovascular disease, hematological disease, cancer, and bone disorders, as well as for modulating cellular differentiation and/or proliferation.

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