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(RP 52028);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
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 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

J & K SCIENTIFIC LTD.
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DC Chemicals
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85532-75-8, 1-(2-CHLOROPHENYL)-N-METHYL-N-(1-METHYLPROPYL)-3-ISOQUINOLINECARBOXAMIDERelated Search:


  • 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)-
  • PK 11195(RP 52028)
  • 85532-75-8
  • Miscellaneous Compounds