tasquinimod
tasquinimod Basic information
- Product Name:
- tasquinimod
- Synonyms:
-
- 4-Hydroxy-5-methoxy-N-methyl-1-methyl-2-oxo-N-(4-trifluoromethylphenyl)-1,2-dihydroquinoline-3-carboxamide
- N-Methyl-N-(4-trifluoromethylphenyl)-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxoquinoline-3-carboxamide
- tasquinimod
- ABR-215050
- 3-QuinolinecarboxaMide, 1,2-dihydro-4-hydroxy-5-Methoxy-N,1-diMethyl-2-oxo-N-[4-(trifluoroMethyl)phenyl]-
- 4-Hydroxy-5-Methoxy-1-Methyl-2-oxo-1,2- dihydro-quinoline-3-carboxylic acid Methyl- (4-trifluoroMethyl-phenyl)-aMide
- 1,2-dihydro-4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-trifluoromethyl)phenyl]-3-quinolinecarboxamide
- 4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-(4-(trifluoromethyl)-phenyl)-1,2-dihydroquinoline-3-c
- CAS:
- 254964-60-8
- MF:
- C20H17F3N2O4
- MW:
- 406.36
- Product Categories:
-
- Angiogenesis inhibitor
- S100 calcium binding protein A9 modulator
- Inhibitors
- Mol File:
- 254964-60-8.mol
tasquinimod Chemical Properties
- Boiling point:
- 501.5±50.0 °C(Predicted)
- Density
- 1.427±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- solubility
- insoluble in H2O; ≥20.32 mg/mL in DMSO; ≥4.75 mg/mL in EtOH with gentle warming and ultrasonic
- form
- solid
- pka
- 4.50±1.00(Predicted)
- color
- White to light yellow
tasquinimod Usage And Synthesis
Description
Tasquinimod is an orally-active quinoline-
Uses
Tasquinimod is an orally active antiangiogenic agent which may inhibit HDAC4 signalling. This affects cancer cell survival thus making this compound and anti-cancer agent.
Synthesis
22864-65-9
248282-18-0
254964-60-8
General procedure for Example 8 N-methyl-N-(4-trifluoromethylphenyl)-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxoquinoline-3-carboxamide (Method B): 1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxoquinoline-3-carboxylic acid (8 g, 0.032 mol) and triethylamine ( 15.5 ml, 0.11 mol) were dissolved in 10 ml of dichloromethane and cooled to 0°C. Within 0.5 h, 150 ml of a dichloromethane solution of thionyl chloride (3.0 ml, 0.042 mol) was added dropwise to this solution while maintaining the temperature at 4°C. After the dropwise addition, stirring was continued at 4°C for 4 hours. After completion of the reaction, the reaction mixture was diluted with 10 ml of dichloromethane and washed sequentially with cold 1 M sulfuric acid and 1 M sodium hydroxide solution. The pH of the aqueous phase was adjusted to 8-8.5, clarified by filtration and acidified with hydrochloric acid to pH 4. Upon standing, a crystalline precipitate was formed, the precipitate was collected by filtration, washed with water and dried to afford the target product 4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-(4-(trifluoromethyl)phenyl)-1,2-dihydroquinoline-3-carboxamide (8.5 g, 65% yield). The product was structurally confirmed by 1H NMR and 13C NMR and analyzed by ESI MS/MS.
in vivo
The bioavailability and oral absorption of Tasquinimod is excellent when adult male mice (i.e., C57Bl/6J, or athymic nude mice) are given 0.1-30 mg/kg (i.e., 0.2-74 μmoles/kg) via gavage or the drinking water. The potency of Tasquinimod expressed as the daily oral dose of Tasquinimod which inhibits cancer growth by 50% ranges from 0.1-1.0 mg/kg/d (i.e., 0.24-2.40 μmoles/kg/day) against a series (n>5) of human prostate cancer xenografts in immune-deficient mice. Tasquinimod at a chronic dose of 5 mg/kg/day via the drinking water produces > 80% inhibition (p<0.05) of TRAMP-C2 mouse prostate cancer growth in immune-competent syngeneic mice[2]. Nude mice carrying subcutaneous LNCaP tumors are treated with Tasquinimod for 3 weeks. Exposure to Tasquinimod at 1 mg/kg/day and 10 mg/kg/day started on day 7 after inoculation. There is a statistically significant dose dependent reduction in tumor weight both at 1 mg/kg/day and 10 mg/kg/day compare to the untreated control group 28 days after inoculation (p<0.001), illustrating the anti-tumor effect of Tasquinimod[3].
target
tumor microenvironment
IC 50
HDAC4: 10-30 nM (Kd)
storage
Store at -20°C
References
[1] Patent: US6133285, 2000, A
[2] Patent: EP1095021, 2003, B1. Location in patent: Page/Page column 9
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