Tasisulam Chemical Properties

Density 

1.812

storage temp. 

Store at -20° C

solubility 

DMF: 20 mg/ml; DMSO: 20 mg/ml; Ethanol: 10 mg/ml; PBS (pH 7.2): 0.2 mg/ml

form 

A crystalline solid

pka

3.45±0.10(Predicted)

color 

Light yellow to yellow

InChI

InChI=1S/C11H6BrCl2NO3S2/c12-9-3-4-10(19-9)20(17,18)15-11(16)7-2-1-6(13)5-8(7)14/h1-5H,(H,15,16)

InChIKey

WWONFUQGBVOKOF-UHFFFAOYSA-N

SMILES

C(NS(C1SC(Br)=CC=1)(=O)=O)(=O)C1=CC=C(Cl)C=C1Cl

Tasisulam Usage And Synthesis

Uses

The sodium salt of Tasisulam has potential antineoplastic activity. Selectively toxic towards tumor cells, tasisulam appears to induce tumor cell apoptosis by a mitochondrial-targeted mechanism involving the loss of mitochondrial membrane potential and induction of reactive oxygen species (ROS).

Biological Activity

Tasisulam (LY573636) is a SPLAM (SPLicing inhibitor sulfonAMide) th at bridges RNA binding motif protein 39 (RBM39; CAPERα, HCC1) and DCAF15 for interaction, thereby promoting (CUL4-DDB1-DDA1-DCAF15) E3 ubiquitin ligase complex-mediated RBM39 ubiquitination and subsequent proteasomal degradation. Tasisulam exerts selective toxicity in parental HCT116 cancer cultures (IC50 = 6.5 μM), but not those harboring non-CUL4-DCAF15-associating RBM39 G268V mutant even at a high concentration of 50 μM.

Synthesis

General procedure for the synthesis of N-(2,4-dichlorobenzoyl)-5-bromothiophene-2-sulfonamide from 2,4-dichlorobenzoic acid and the compound (CAS:1152981-12-8): 0.5 mmol (0.0955 g) of 2,4-dichlorobenzoic acid, 0.75 mmol (0.2011 g) of 2-bromothiophene-sulfonamide azide, and 0.025 mmol (0.0086 g) octacarbonyldicobalt in a 25 mL reaction tube; subsequently, 4 mL of acetonitrile solvent was added via a microsyringe, and the reaction system was stirred at 80 °C for 4 hours. Upon completion of the reaction, the mixture was concentrated by rotary evaporation and purified by column chromatography (column conditions: 200-300 mesh silica gel, mobile phase ethyl acetate:petroleum ether=1:4) to give 0.1583 g of the target product as a white solid in 76% yield.

References

[1] Chemistry--A European Journal, 2012, vol. 18, # 45, p. 14444 - 14453,10
[2] Chemistry - A European Journal, 2012, vol. 18, # 45, p. 14444 - 14453
[3] Journal of Organic Chemistry, 2018, vol. 83, # 16, p. 9364 - 9369
[4] Patent: CN108558822, 2018, A. Location in patent: Paragraph 0035; 0036; 0037; 0040; 0043

Tasisulam(519055-62-0)Related Product Information

• Benzenesulfonamide
• Cyclopropanesulfonamide
• 3-Aminobenzenesulfonamide
• Sulfanilamide
• Methanesulfonamide
• p-Toluenesulfonamide
• Tazemetostat
• GDC-0032
• tasquinimod
• PAC1
• CX-4945
• Ibrutinib
• CRA-02478
• AZD-9291
• Olaparib
• 5-Bromothiophene-2-sulfonamide
• Tasisulam