ChemicalBook > CAS DataBase List > BAY 41-2272

BAY 41-2272

Product Name
BAY 41-2272
CAS No.
256376-24-6
Chemical Name
BAY 41-2272
Synonyms
IN1523;UNII-34A162J6WB;BAY 41-2272 (BAY 412272;BAY 41-2272, 10 mM in DMSO;BAY 41-2272, Soluble guanylyl cyclase (sGC) activator;Inhibitor,inhibit,Guanylate Cyclase,BAY 41 2272,BAY 412272,BAY 41-2272;3-(4-Amino-5-cyclopropylpyrimidin-2-yl)-1-(2-fluorobenzyl)-1H-pyrazolo[3;5-Cyclopropyl-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-amine;5-cyclopropyl-2-[1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-4-amine;5-Cyclopropyl-2-[1-[(2-fluorophenyl)Methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-pyriMidinaMine
CBNumber
CB9497944
Molecular Formula
C20H17FN6
Formula Weight
360.39
MOL File
256376-24-6.mol
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BAY 41-2272 Property

Melting point:
210.5-211.4 °C
Boiling point:
496.1±45.0 °C(Predicted)
Density 
1.49±0.1 g/cm3(Predicted)
storage temp. 
Keep in dark place,Inert atmosphere,2-8°C
solubility 
DMSO: 26 mg/mL at 60 °C
form 
solid
pka
2.71±0.10(Predicted)
color 
white
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
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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
B8810
Product name
BAY 41-2272
Purity
≥97% (HPLC)
Packaging
5 mg
Price
$241
Updated
2025/07/31
Sigma-Aldrich
Product number
B8810
Product name
BAY 41-2272
Purity
≥97% (HPLC)
Packaging
25 mg
Price
$724
Updated
2025/07/31
Sigma-Aldrich
Product number
196876
Product name
BAY 41-2272 - CAS 256376-24-6 - Calbiochem
Packaging
5mg
Price
$219
Updated
2025/07/31
Cayman Chemical
Product number
10057
Product name
BAY 41-2272
Purity
≥95%
Packaging
5mg
Price
$106
Updated
2024/03/01
Cayman Chemical
Product number
10057
Product name
BAY 41-2272
Purity
≥95%
Packaging
10mg
Price
$198
Updated
2024/03/01
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BAY 41-2272 Chemical Properties,Usage,Production

Description

Soluble guanylate cyclase (sGC), a receptor for nitric oxide (NO), is a heterodimer consisting of alpha and beta subunits, with the beta subunit featuring a heme-nitric oxide (H-NOX) binding domain. The binding of NO to H-NOX induces sGC to generate the second messenger cGMP. BAY 41-2272 is a pyrazolopyridine compound that acts as an activator of sGC, stimulating activity to a level that would be expected to cause biologically important increases in cGMP at concentrations as low as 10-100 nM. Through this effect, it inhibits platelet aggregation (IC50 = 36 nM), induces relaxation of phenylephrine-preconstricted rabbit aorta rings (IC50 = 304 nM), and reduces proliferation in smooth muscle. BAY 41-2272 is effective in vivo, as it decreases mean arterial blood pressure in hypertensive rats. Unlike another sGC activator, YC-1 , BAY 41-2772 does not inhibit phosphodiesterases.

Uses

BAY 41-2272 is a soluble guanylate cyclase agonist that activates human mononuclear phagocytes. Inhibits vascular smooth muscle growth through the cAMP-dependent protein kinase and cGMP-dependent protein kinase pathways.

Definition

ChEBI: BAY 41-2272 is a pyrazolopyridine that is 1H-pyrazolo[3,4-b]pyridine which is substituted by a 2-fluorobenzyl group at position 1 and by a 4-amino-5-cyclopropylpyrimidin-2-yl group at position 3. It is an activator of soluble guanylate cyclase. It has a role as a soluble guanylate cyclase activator, a platelet aggregation inhibitor, a vasodilator agent and an antihypertensive agent. It is a pyrazolopyridine, a member of monofluorobenzenes, an aminopyrimidine and a member of cyclopropanes.

General Description

A cell-permeable pyrazolopyridinylpyrimidine compound that acts as a selective and potent stimulator of soluble guanylate cyclase (effective dose ~ 0.1 nM to 100 μM using recombinant soluble guanylate cyclase). The mode of activation is NO-independent and appears to be mediated through direct binding to the α1 and α2 subunits. Shown to be effective in treating numerous cardiovascular conditions in animal models. Inhibits phenylephrine-induced constriction of rabbit aortic rings (IC50 = 304 nM) and blocks collagen-induced aggregation of human platelets (IC50 = 36 nM). Does not inhibit phosphodiesterases.

Biochem/physiol Actions

Cell permeable: yes

Synthesis

256376-79-1

256376-68-8

256376-24-6

The general procedure for the synthesis of 5-cyclopropyl-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-amine from 2-cyclopropyl-3-oxopropanenitrile and 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-amine was as follows: 103.7 mg (0.38 mmol) of 1-(2-fluorobenzyl )-1H-pyrazolo[3,4-B]pyridine-3-carboxamidine and 168.1 mg (1.54 mmol) of crude 2-cyclopropyl-3-oxopropanenitrile were dissolved in 0.5 ml of toluene and mixed thoroughly in an ultrasonic bath. Subsequently, the toluene was evaporated under reduced pressure, and the mixture was transferred to an open vessel and heated to 100-105 °C for 1 h under solvent-free conditions for the reaction. Upon completion of the reaction, the mixture was cooled to room temperature and the residue was dissolved in dichloromethane and mixed with 1 g of silica gel, followed by concentration of the mixture using a rotary evaporator. To purify the product, the separation was carried out by column chromatography on silica gel 60 (particle size 0.040-0.063 mm) with cyclohexane/ethyl acetate (1:1) as mobile phase. The final product was obtained as 50.0 mg with a yield of 36.0% of the theoretical value. Thin layer chromatography (TLC) analysis showed an Rf value of 0.23 (SiO2, ethyl acetate/cyclohexane).

storage

Store at +4°C

References

[1] Patent: US6833364, 2004, B1. Location in patent: Page column 37,38
[2] Patent: US6833364, 2004, B1. Location in patent: Page column 37

BAY 41-2272 Preparation Products And Raw materials

Raw materials

Preparation Products

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BAY 41-2272 Suppliers

Canada 1 China 66 India 2 Switzerland 1 United Kingdom 1 United States 12 Global 83
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Shanghai CanSpecsci Instrument Co., Ltd.
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256376-24-6, BAY 41-2272Related Search:

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  • BAY 41-2272; 256376-24-6; UNII-34A162J6WB; IN1523; BAY-41-2272; 3-(4-AMINO-5-CYCLOPROPYLPYRIMIDIN-2-YL)-1-(2-FLUOROBENZYL)-1H-PYRAZOLO[3;4-B]PYRIDINE
  • IN1523
  • UNII-34A162J6WB
  • 3-(4-Amino-5-cyclopropylpyrimidin-2-yl)-1-(2-fluorobenzyl)-1H-pyrazolo[3
  • 5-Cyclopropyl-2-[1-[(2-fluorophenyl)Methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-pyriMidinaMine
  • 5-Cyclopropyl-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-amine
  • 4-Pyrimidinamine, 5-cyclopropyl-2-[1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-
  • Inhibitor,inhibit,Guanylate Cyclase,BAY 41 2272,BAY 412272,BAY 41-2272
  • 5-cyclopropyl-2-[1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-4-amine
  • BAY 41-2272, Soluble guanylyl cyclase (sGC) activator
  • BAY 41-2272, 10 mM in DMSO
  • BAY 41-2272 (BAY 412272
  • 256376-24-6
  • Pharmaceuticals, Intermediates & Fine Chemicals, Inhibitors