ChemicalBook--->CAS DataBase List--->774549-97-2

774549-97-2

774549-97-2 Structure

774549-97-2 Structure
IdentificationBack Directory
[Name]

KM 11060
[CAS]

774549-97-2
[Synonyms]

KM 11060
KM11060;KM-11060
CFTR-F508del Corrector, KM11060
7-CHLORO-4-(4-(4-CHLOROPHENYLSULFONYL)PIPERAZIN-1-YL)QUINOLINE
7-CHLORO-4-[4-[4-CHLOROPHENYL)SULFONYL]-1-PIPERAZINYL]QUINOLINE
Quinoline, 7-chloro-4-[4-[(4-chlorophenyl)sulfonyl]-1-piperazinyl]-
[Molecular Formula]

C19H17Cl2N3O2S
[MDL Number]

MFCD01524977
[MOL File]

774549-97-2.mol
[Molecular Weight]

422.33
Chemical PropertiesBack Directory
[storage temp. ]

Store at RT
[solubility ]

Soluble to 100 mM in DMSO and to 10 mM in ethanol
[form ]

Powder
[color ]

White to off-white
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[Hazard Codes ]

T
[Risk Statements ]

25
[Safety Statements ]

45
Hazard InformationBack Directory
[Uses]

KM 11060 is a small molecular corrector of F508del CFTR trafficking, which has potential application in cystic fibrosis therapeutics.
[Biological Activity]

Corrects F508del-CFTR trafficking; increases the amount of functional CFTR at the plasma membrane (~75%). Shown to inhibit PDE5 activity.
[Synthesis]

4-Chlorobenzenesulfonyl chloride

98-60-2

7-Chloro-4-piperazinoquinoline

837-52-5

KM 11060

774549-97-2

To a stirred solution of 7-chloro-4-(1-piperazinyl)quinoline (0.25 g, 1 mmol) in dichloromethane (8-10 mL) at 0 °C was added triethylamine (0.12 mL, 1.26 mmol). Subsequently, 4-chlorobenzenesulfonyl chloride (1 mmol) was added dropwise or in batches, and the reaction mixture was continued to be stirred at 0 °C for 15 min, then brought to room temperature and stirred until the reaction was complete (monitored by TLC). Upon completion of the reaction, the reaction mixture was diluted with dichloromethane (20 mL) and water (20 mL) and transferred to a partition funnel for separation. The organic layer was washed with water (3 x 20 mL) and dried over anhydrous sodium sulfate. Recrystallization by mixed solvent recrystallization of dichloromethane and hexane afforded pure 7-chloro-4-(4-((4-chlorophenyl)sulfonyl)-1-piperazinyl)quinoline in 85-95% yield.

[in vivo]

In LPS-induced acute lung inflammation, blockade of PSGL-1 (P-selectin glycoprotein ligand-1) or P-selectin, antagonism of PAF by WEB2086, or correction of mutated CFTR trafficking by KM11060 could significantly increase plasma lipoxin A4 levels in F508del relevant to wildtype mice. [2]

[storage]

Store at RT
[References]

[1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 3080 - 3089
Spectrum DetailBack Directory
[Spectrum Detail]

KM 11060(774549-97-2)1HNMR
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