2-(2-chlorophenyl)-4-Methyl-5-(pyridin-2-ylMethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione

Product Name: 2-(2-chlorophenyl)-4-Methyl-5-(pyridin-2-ylMethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
CAS No.: 955272-06-7
Chemical Name: 2-(2-chlorophenyl)-4-Methyl-5-(pyridin-2-ylMethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
Synonyms: AK120765;GKT136901;GKT136901, 10 mM in DMSO;NOX Inhibitor IV, GKT136901;2-(2-chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6-dione;2-(2-chlorophenyl)-4-Methyl-5-(pyridin-2-ylMethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;1H-Pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione, 2-(2-chlorophenyl)-4-methyl-5-(2-pyridinylmethyl)-;2-(2-chlorophenyl)-4-methyl-5-[(pyridin-2-yl)methyl]-1H,2H,3H,5H,6H-pyrazolo[4,3-c]pyridine-3,6-dione;peroxynitrite,scavenger,neurodegeneration,NOX1/4,NADPH,oxidase,inhibit,NOX,NADPH Oxidase,GKT-136901,GKT 136901,nephropathy,anti-inflammatory,GKT136901,stroke,Inhibitor,diabetic
CBNumber: CB02598866
Molecular Formula: C19H15ClN4O2
Formula Weight: 366.8
MOL File: 955272-06-7.mol

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2-(2-chlorophenyl)-4-Methyl-5-(pyridin-2-ylMethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione Property

Boiling point:: 530.2±60.0 °C(Predicted)
Density: 1.48±0.1 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: DMF:25.0(Max Conc. mg/mL);68.16(Max Conc. mM)
DMSO:30.0(Max Conc. mg/mL);81.79(Max Conc. mM)
DMSO:PBS (pH 7.2) (1:6):0.14(Max Conc. mg/mL);0.38(Max Conc. mM)
Ethanol:1.0(Max Conc. mg/mL);2.73(Max Conc. mM)
form: A solid
pka: 4.22±0.12(Predicted)
color: Off-white to light brown

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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

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

P280Wear protective gloves/protective clothing/eye protection/face protection.

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: 5.34032
Product name: NOX Inhibitor IV, GKT136901 - CAS 955272-06-7 - Calbiochem
Purity: Potent, orally available dual inhibitor of NOX1/NOX4. Blocks NOX-mediated ROS outburst and efficiently scavenges peroxynitrite.
Packaging: 10MG
Price: $182
Updated: 2025/07/31

ChemScene

Product number: CS-0021553
Product name: GKT136901
Packaging: 50mg
Price: $200
Updated: 2021/12/16

ChemScene

Product number: CS-0021553
Product name: GKT136901
Packaging: 5mg
Price: $50
Updated: 2021/12/16

ChemScene

Product number: CS-0021553
Product name: GKT136901
Packaging: 10mg
Price: $75
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: HCH0356950
Product name: 2-(2-CHLOROPHENYL)-4-METHYL-5-(PYRIDIN-2-YLMETHYL)-1H-PYRAZOLO[4,3-C]PYRIDINE-3,6(2H,5H)-DIONE
Purity: 95.00%
Packaging: 5MG
Price: $499.32
Updated: 2021/12/16

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2-(2-chlorophenyl)-4-Methyl-5-(pyridin-2-ylMethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione Chemical Properties,Usage,Production

Uses

GKT136901 is a potent, selective and orally active inhibitor of NADPH oxidase (NOX1/4), with Kis of 160 and 165 nM, respectively. GKT136901 is also a selective and direct scavenger of peroxynitrite. GKT136901 can be used for the research of diabetic nephropathy, stroke, and neurodegeneration. GKT136901 also has anti-inflammatory activity[1][2][3].

Biological Activity

Cell permeable: yes', 'Primary Target
NOX1- and NOX4-containing NADPH oxidase activity', 'Reversible: yes

Synthesis

1217897-99-8

955272-06-7

d) Synthesis of 2-(2-chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione (Compound (Ia) of formula (II), Scheme 1): an isopropanol solution of sodium isopropoxide was prepared by dissolving sodium (0.082 g, 3.57 mmol, 1 equiv.) in isopropanol (75 mL). To this solution was added methyl [(4E)-1-(2-chlorophenyl)-5-oxo-4-{[(pyridin-2-ylmethyl)amino]ethylidene}-4,5-dihydro-1H-pyrazol-3-yl]acetate (compound of formula (VIII), 1.42 g, 3.57 mmol). The reaction mixture was refluxed for 1 hour and subsequently cooled to room temperature. It was neutralized with 20% aqueous hydrochloric acid (0.59 mL) to pH 7. After removing 50 mL of isopropanol by distillation under reduced pressure, 25 mL of water was added. The reaction flask was placed in a refrigerator overnight and a white precipitate was precipitated. The precipitate was collected by filtration, washed sequentially with water (2 x 5 mL) and cyclohexane, and dried under vacuum to afford the pure product 2-(2-chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione 1.07 g in 82% yield.1H-NMR (500 MHz, DMSO-d6, ppm) : 2.78 (s, 3H), 5.41 (s, 2H), 5.66 (s, 1H), 7.31-7.28 (m, 1H), 7.32 (d, J=7.9 Hz, 1H), 7.50-7.47 (m, 2H), 7.60-7.56 (m, 1H), 7.66-7.64 (m, 1H), 7.79 (td, J=7.6 ,1.9 Hz, 1H), 8.48 (m, 1H), 10.73 (s, br, 1H).MS (ESI+): 367.9; MS (ESI-): 365.7.

in vivo

GKT136901 (30-90 mg/kg; daily p.o. for 16 weeks) has renoprotective effects in a mouse model of Type 2 diabetes^[6].

Animal Model:	Male db/db and db/m mice (8 weeks)^[6]
Dosage:	30, 90 mg/kg
Administration:	Daily p.o. for 16 weeks
Result:	Reduced albuminuria, thiobarbituric acid-reacting substances (TBARS) and renal ERK1/2 phosphorylation and preserved renal structure in diabetic mice. Had no effect on plasma glucose, BP (blood pressure), and body weight.

IC 50

NOX1; NOX4

References

[1] Laleu B, et, al. First in class, potent, and orally bioavailable NADPH oxidase isoform 4 (Nox4) inhibitors for the treatment of idiopathic pulmonary fibrosis. J Med Chem. 2010 Nov 11;53(21):7715-30. DOI:10.1021/jm100773e
[2] Teixeira G, et, al. Therapeutic potential of NADPH oxidase 1/4 inhibitors. Br J Pharmacol. 2017 Jun;174(12):1647-1669. DOI:10.1111/bph.13532
[3] Schildknecht S, et, al. The NOX1/4 inhibitor GKT136901 as selective and direct scavenger of peroxynitrite. Curr Med Chem. 2014;21(3):365-76. DOI:10.2174/09298673113209990179
[4] Sedeek M, et, al. Critical role of Nox4-based NADPH oxidase in glucose-induced oxidative stress in the kidney: implications in type 2 diabetic nephropathy. Am J Physiol Renal Physiol. 2010 Dec;299(6):F1348-58. DOI:10.1152/ajprenal.00028.2010
[5] Hwang JS, et, al. GKT136901 protects primary human brain microvascular endothelial cells against methamphetamine-induced blood-brain barrier dysfunction. Life Sci. 2020 Sep 1;256:117917. DOI:10.1016/j.lfs.2020.117917
[6] Sedeek M, et, al. Renoprotective effects of a novel Nox1/4 inhibitor in a mouse model of Type 2 diabetes. Clin Sci (Lond). 2013 Feb;124(3):191-202. DOI:10.1042/CS20120330

2-(2-chlorophenyl)-4-Methyl-5-(pyridin-2-ylMethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione Preparation Products And Raw materials

Raw materials

Preparation Products

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2-(2-chlorophenyl)-4-Methyl-5-(pyridin-2-ylMethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione Suppliers

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View Lastest Price from 2-(2-chlorophenyl)-4-Methyl-5-(pyridin-2-ylMethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione manufacturers

Career Henan Chemical Co

Product: 2-(2-chlorophenyl)-4-Methyl-5-(pyridin-2-ylMethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione 955272-06-7
Price: US $1.00/KG
Min. Order: 1KG
Purity: 98% HPLC
Supply Ability: 10 Tons
Release date: 2020-02-19

955272-06-7, 2-(2-chlorophenyl)-4-Methyl-5-(pyridin-2-ylMethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dioneRelated Search:

2-(2-chlorophenyl)-4-Methyl-5-(pyridin-2-ylMethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione

AK120765

2-(2-chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6-dione

GKT136901

1H-Pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione, 2-(2-chlorophenyl)-4-methyl-5-(2-pyridinylmethyl)-

peroxynitrite,scavenger,neurodegeneration,NOX1/4,NADPH,oxidase,inhibit,NOX,NADPH Oxidase,GKT-136901,GKT 136901,nephropathy,anti-inflammatory,GKT136901,stroke,Inhibitor,diabetic

2-(2-chlorophenyl)-4-methyl-5-[(pyridin-2-yl)methyl]-1H,2H,3H,5H,6H-pyrazolo[4,3-c]pyridine-3,6-dione

GKT136901, 10 mM in DMSO

NOX Inhibitor IV, GKT136901

955272-06-7