| Identification | Back Directory | [Name]
TM5441 | [CAS]
1190221-43-2 | [Synonyms]
TM5441
CS-2510
TM 5441;TM-5441
Benzoic acid, 5-chloro-2-[[2-[2-[[3-(3-furanyl)phenyl]amino]-2-oxoethoxy]acetyl]amino]- | [Molecular Formula]
C21H17ClN2O6 | [MDL Number]
MFCD31382187 | [MOL File]
1190221-43-2.mol | [Molecular Weight]
428.82 |
| Chemical Properties | Back Directory | [Boiling point ]
738.6±60.0 °C(Predicted) | [density ]
1.451±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 33 m/ml; DMF:PBS(pH 7.2)(1:6): 0.14 mg/ml; DMSO: 20 mg/ml | [form ]
A crystalline solid | [pka]
2.87±0.10(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Uses]
TM5441 is a novel plasminogen activator inhibitor 1 (PAI-1). A therapeutic agent for obesity and obesity-related metabolic disorders. | [Synthesis]
GENERAL METHOD: Ester compound 12a (0.46 g, 1.17 mmol) was dissolved in tetrahydrofuran (4.6 mL) and 1 N aqueous sodium hydroxide solution (1.29 mL) was added. The reaction mixture was stirred at 50 °C for 3 hours. After completion of the reaction, it was cooled to room temperature and the tetrahydrofuran was removed by distillation under reduced pressure. The residue was acidified with 1 N hydrochloric acid and the resulting precipitate was collected by filtration. The precipitate was washed sequentially with water and isopropyl ether and dried under vacuum to afford the target carboxylic acid compound 24 as a solid (0.425 g, 96% yield). | [in vivo]
Oral administration of TM5441 (20 mg/kg daily) to HT1080 and HCT116 xenotransplanted mice increases tumor cell apoptosis and has a significant disruptive effect on the tumor vasculature that is associated with a decrease in tumor growth and an increase in survival. The average peak plasma concentration is 11.4 μM one hour after oral administration and undetectable levels 23 hours after administration[1].
TM5441 attenuates Nω-nitro-l-arginine methyl ester-induced cardiac hypertension and vascular senescence, prolongs lifespan in klotho null mice and elicits anti-tumorigenic and anti-angiogenic activities in cancer[3]. | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 4, p. 809 - 813 |
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