| Identification | Back Directory | [Name]
Tasisulam | [CAS]
519055-62-0 | [Synonyms]
CS-519
TS81557
Tssolan
Ly573636
Ly-573636
tasisulam
LY573636-sodium
Tasisulam, >=98%
Tasisulam(Ly-573636
Tasisulam USP/EP/BP
LY573636 (TasisulaM)
TASISULAMUM TASISULAM
LY573636-SODIUM; BENZAMIDE
LY573636-SODIUM; BENZAMIDE;LY573636
N-(2,4-Dichlorobenzoyl)-5-bromothiophene-2-sulfonamide
N-(5-Bromothiophen-2-ylsulfonyl)-2,4-dichlorobenzamide
Benzamide, N-((5-bromo-2-thienyl)sulfonyl)-2,4-dichloro-
Tasisulam
N-(2,4-Dichlorobenzoyl)-5-bromothiophene-2-sulfonamide
N-(2,4-Dichlorobenzoyl)-5-bromothiophene-2-sulfonamide LY573636 Tasisulam | [Molecular Formula]
C11H6BrCl2NO3S2 | [MDL Number]
MFCD11973637 | [MOL File]
519055-62-0.mol | [Molecular Weight]
415.11 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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; CAPERαHCC1) and DCAF15 for interactionthereby 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 |
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