1-(2-CHLOROPHENYL)-N-METHYL-N-(1-METHYLPROPYL)-3-ISOQUINOLINECARBOXAMIDE

ChemicalBook > CAS DataBase List > 1-(2-CHLOROPHENYL)-N-METHYL-N-(1-METHYLPROPYL)-3-ISOQUINOLINECARBOXAMIDE

1-(2-CHLOROPHENYL)-N-METHYL-N-(1-METHYLPROPYL)-3-ISOQUINOLINECARBOXAMIDE

Product Name: 1-(2-CHLOROPHENYL)-N-METHYL-N-(1-METHYLPROPYL)-3-ISOQUINOLINECARBOXAMIDE
CAS No.: 85532-75-8
Chemical Name: 1-(2-CHLOROPHENYL)-N-METHYL-N-(1-METHYLPROPYL)-3-ISOQUINOLINECARBOXAMIDE
Synonyms: PK 11195;PK 11195 PERIPHERAL BENZODIAZE;1-(2-chlorophenyl)-N-methyl-*N-(1-methylpropyl)-3;chlorophenylmethyl(1-methylpropyl)isoquinolinecarboxamide;1-(2-Chlorophenyl)-N-(1-methylpropyl)-3-isoquinolinecarboxamide;1-(2-chlorophenyl)-n-methyl-n-(1-methylpropyl)-3-isoquinolinecarboxamid;N-Methyl-N-(1-methylpropyl)-1-(2-chlorophenyl)-3-isoquinolinecarboxamide;1-(2-CHLOROPHENYL)-N-METHYL-N-(1-METHYLPROPYL)-3-ISOQUINOLINECARBOXAMIDE;n-methyl-n-(1-methylpropyl)-1-(2-chlorophenyl)isoquinoline-3-carboxamide;3-Isoquinolinecarboxamide, 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)-
CBNumber: CB6102434
Molecular Formula: C21H21ClN2O
Formula Weight: 352.86
MOL File: 85532-75-8.mol

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1-(2-CHLOROPHENYL)-N-METHYL-N-(1-METHYLPROPYL)-3-ISOQUINOLINECARBOXAMIDE Property

Boiling point:: 511.7±45.0 °C(Predicted)
Density: 1.179±0.06 g/cm3(Predicted)
storage temp.: Store at RT
solubility: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 15 mg/ml).
form: White crystalline powder.
pka: 1.76±0.50(Predicted)
color: White
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored under nitrogen or argon at -20° for up to 1 month.
CAS DataBase Reference: 85532-75-8(CAS DataBase Reference)

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Safety

WGK Germany: 3
RTECS: NW6987000

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: C0424
Product name: PK 11195
Packaging: 10mg
Price: $132
Updated: 2024/03/01

Sigma-Aldrich

Product number: C0424
Product name: PK 11195
Packaging: 50mg
Price: $287.4
Updated: 2024/03/01

Sigma-Aldrich

Product number: 5.05981
Product name: PK11195 - CAS 85532-75-8 - Calbiochem
Packaging: 10mg
Price: $104
Updated: 2024/03/01

Cayman Chemical

Product number: 10525
Product name: PK 11195
Purity: ≥98%
Packaging: 10mg
Price: $81
Updated: 2024/03/01

Cayman Chemical

Product number: 10525
Product name: PK 11195
Purity: ≥98%
Packaging: 50mg
Price: $278
Updated: 2024/03/01

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1-(2-CHLOROPHENYL)-N-METHYL-N-(1-METHYLPROPYL)-3-ISOQUINOLINECARBOXAMIDE Chemical Properties,Usage,Production

Description

PK-11195 (85532-75-8) is a selective and potent peripheral benzodiazepine receptor, PBR (or TSPO, translocator protein) antagonist.1,2 It has been shown to chemosensitize tumor cells to a variety of chemotherapeutic agents via PBR-independent pathways.3,4 PK-11195 is also able to induce apoptosis in a variety of cell lines.5-7

Uses

PK 11195 is a high affinity peripheral benzodiazepine receptor (PBR) ligand. PK 11195 has been shown to regulate protein phosphorylation in rat brain mitochondria under control of Ca2+. PK11195 promot es mitochondrial apoptosis and blocks P-glycoprotein (Pgp)-mediated drug efflux to chemosensitize cancer cells.

Uses

PK 11195 is a high affinity peripheral benzodiazepine receptor (PBR) ligand. PK 11195 has been shown to regulate protein phosphorylation in rat brain mitochondria under control of Ca2+. PK11195 promotes mitochondrial apoptosis and blocks P-glycoprotein (Pgp)-mediated drug efflux to chemosensitize cancer cells.

Definition

ChEBI: A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 1-(2-chlorophenyl)isoquinoline-3-carboxylic acid with the amino group of sec-butylmethylamine

Biological Activity

Possesses high affinity for the MDR (peripheral benzodiazepine receptor) without binding to other known neurotransmitter receptors.

Biochem/physiol Actions

PK 11195 is a peripheral benzodiazepine antagonist. It is also an antagonist for human constitutive androstane receptor (hCAR) and human pregnane X receptor (PXR). In human primary hepatocytes, PK 11195 upon demethylation elicits agonist functionality towards the receptor hCAR. PK 11195 also antagonise B-cell lymphoma 2 (Bcl-2) and may serve as a potential compound for mitochondrial targeting therapies and in the treatment of cholangiocarcinoma.

storage

Room temperature

References

1) Le Fur, et al.; (1983) Peripheral benzodiazepine binding sites: effect of PK 11195, 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide. I. In vitro studies; Life Sci., 32 1839 2) Le Fur et al.; (1983) Peripheral benzodiazepine binding sites: effect of PK 11195, 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide. II. In vivo studies; Life Sci., 32 1849 3) Gonzalez-Polo et al. (2005) PK11195 potently sensitizes to apoptosis induction independently from the peripheral benzodiazepine receptor; Oncogene, 24 7503 4) Walter et al. (2005) PK11195, a peripheral benzodiazepine receptor (pBR) ligand, broadly blocks drug efflux to chemosensitize leukemia and myeloma cells by a pBR-independent, direct transporter-modulating mechanism; Blood, 106 3584 5) Chelli et al. (2004) Peripheral benzodiazepine receptor ligands:mitochondrial transmembrane potential depolarization and apoptosis induction in rat C6 glioma cells; Biochem. Pharmacol., 68 125 6) Sutter et al. (2004) Peripheral benzodiazepine receptor ligands induce apoptosis and cell cycle arrest in human hepatocellular carcinoma cells and enhance chemosensitivity to paclitaxel, docetaxel, doxorubicin and the Bcl-2-inhibitor HA14-1; J. Hepatol., 120 1212 7) Maaser et al. (2001) Specific ligands of the peripheral benzodiazepine receptor induce apoptosis and cell cycle arrest in human colorectal cancer cells; Br. J. Cancer, 85 1771

1-(2-CHLOROPHENYL)-N-METHYL-N-(1-METHYLPROPYL)-3-ISOQUINOLINECARBOXAMIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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1-(2-CHLOROPHENYL)-N-METHYL-N-(1-METHYLPROPYL)-3-ISOQUINOLINECARBOXAMIDE Suppliers

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85532-75-8, 1-(2-CHLOROPHENYL)-N-METHYL-N-(1-METHYLPROPYL)-3-ISOQUINOLINECARBOXAMIDERelated Search:

6-METHYL-2-PICOLYL-METHYLAMINE 2-Picolylamine 6-Methyl-2-pyridinemethanamine 2-METHYL-6-PHENYLPYRIDINE 1-METHYLISOQUINOLINE 1-Tetradecanol PYRIDINE-2-CARBOXAMIDE 3-Methylisoquinoline METHYLPYRIDIN-2-YLMETHYLAMINE DIHYDROCHLORIDE 3-isoquinolinecarboxaldehyde 1-(2-CHLOROPHENYL)-N-(1-METHYLPROPYL)-ISOQUINOLINE-3-CARBOXAMIDE Phenylisoquinoline CHEMBRDG-BB 9070750 N-(pyridin-2-ylmethyl)propan-1-amine 6-(4-fluorophenyl)pyridine-2-carbaldehyde 1-(2-CHLOROPHENYL)-N-METHYL-N-(1-METHYLPROPYL)-3-ISOQUINOLINECARBOXAMIDE 2-Pyridinecarboxamide,6-methyl-(9CI) (R)-PK11195

1-(2-chlorophenyl)-n-methyl-n-(1-methylpropyl)-3-isoquinolinecarboxamid

n-methyl-n-(1-methylpropyl)-1-(2-chlorophenyl)isoquinoline-3-carboxamide

1-(2-CHLOROPHENYL)-N-METHYL-N-(1-METHYLPROPYL)-3-ISOQUINOLINECARBOXAMIDE

PK 11195

1-(2-chlorophenyl)-N-methyl-*N-(1-methylpropyl)-3

PK 11195 PERIPHERAL BENZODIAZE

1-(2-Chlorophenyl)-N-(1-methylpropyl)-3-isoquinolinecarboxamide

chlorophenylmethyl(1-methylpropyl)isoquinolinecarboxamide

N-Methyl-N-(1-methylpropyl)-1-(2-chlorophenyl)-3-isoquinolinecarboxamide

3-Isoquinolinecarboxamide, 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)-

85532-75-8

Miscellaneous Compounds