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301326-22-7

301326-22-7 Structure

301326-22-7 Structure
IdentificationBack Directory
[Name]

1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide
[CAS]

301326-22-7
[Synonyms]

CS-2720
CH 223191
AhR Antagonist
CH223191;CH 223191
AhR Antagonist - CAS 301326-22-7 - Calbiochem
2-methyl-N-[2-methyl-4-[(2-methylphenyl)diazenyl]phenyl]pyrazole-3-c
2-Methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazo-phenyl)-amide
(E)-1-methyl-N-(2-methyl-4-(o-tolyldiazenyl)phenyl)-1H-pyrazole-5-carboxamide
1-Methyl-N-[2-methyl-4-[(2-methylphenyl)azo]phenyl]-1H-pyrazole-5-carboxamide
2-methyl-N-[2-methyl-4-[(2-methylphenyl)diazenyl]phenyl]pyrazole-3-carboxamide
1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide
1H-Pyrazole-5-carboxamide, 1-methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl]-
1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide USP/EP/BP
[Molecular Formula]

C19H19N5O
[MDL Number]

MFCD00377884
[MOL File]

301326-22-7.mol
[Molecular Weight]

333.387
Chemical PropertiesBack Directory
[Melting point ]

>164°C (dec.)
[Boiling point ]

469.4±45.0 °C(Predicted)
[density ]

1.20±0.1 g/cm3(Predicted)
[storage temp. ]

Store at +4°C
[solubility ]

DMSO: ≥20mg/mL
[form ]

powder
[pka]

12.98±0.70(Predicted)
[color ]

orange-brown
[Stability:]

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
[InChIKey]

LKTNEXPODAWWFM-GHVJWSGMSA-N
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

22
[Safety Statements ]

22
[WGK Germany ]

3
Hazard InformationBack Directory
[Description]

CH-221391 (CAS 301326-22-7) is an arylhydrocarbon (AhR) receptor antagonist, IC50=30 nM.1 Blocks endogenous AhR agonist-induced differentiation of Th17 cells.2?? Promotes expansion of human hematopoietic stem cells.3 Mitigates cytokine-mediated inflammatory signaling in human fibroblast-like synoviocytes.4 An important tool for probing the involvement of AhR in the toxicity of various environmental toxins such as TCDD and other dioxins.5
[Uses]

CH-223191 has been used as aryl hydrocarbon receptor (AHR) antagonist in HepaRG cells, TH17-IL-10+ cells and organoids.
[Definition]

ChEBI: 2-methyl-N-[2-methyl-4-(2-methylphenyl)azophenyl]-3-pyrazolecarboxamide is an aromatic amide.
[Biochem/physiol Actions]

CH-223191 is a potent and specific aryl hydrocarbon receptor (AhR) antagonist. It inhibited TCDD-mediated nuclear translocation and DNA binding of AhR, and inhibited TCDD-induced luciferase activity with an IC50 of 30nM. Unlike some other AhR antagonists which display agonist activity at high concentrations, CH-223191 did not stimulate AhR-dependent transcription even at 100 micromolar. It is also specific for AhR, displaying no affinity for the estrogen receptor, as some other antagonists do.
[storage]

Store at -20°C
[References]

1) Kim et al. (2006), Novel compound 2-methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazo-phenyl)amide (CH-223191) prevents 2,3,7,8-TCDD-induced toxicity by antagonizing the aryl hydrocarbon receptor; Mol. Pharmacol., 69 1871 2) Veldhoen et al. (2009), Natural agonists for aryl hydrocarbon receptor in culture medium are essential for optimal differentiation of Th17 T cells; J. Exp. Med., 206 43 3) Carlin et al. (2013), T-cell potential of human adult and cord blood hemopoietic stem cells expanded with the use of aryl hydrocarbon receptor antagonists; Cytotherapy, 15 224 4) Lahoti et al. (2013), Aryl hydrocarbon receptor antagonism mitigates cytokine-mediated inflammatory signaling in primary human fibroblast-like synoviocytes; Ann. Rheum. Dis, 72 1708 5) Petroff et al. (2011), The aryl hydrocarbon receptor agonist 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) alters early embryonic development in a rat IVF exposure model; Reprod. Toxicol., 32 286
Spectrum DetailBack Directory
[Spectrum Detail]

1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide(301326-22-7)1HNMR
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