| Identification | Back Directory | [Name]
S3I-201 | [CAS]
501919-59-1 | [Synonyms]
CS-450
106202
S31-201
S3I-201
S2I-201
NSC 74859
S3I-201, >98%
NSC 74859, >=98%
S3I-201 USP/EP/BP
NSC 74859(S31-201)
OTAVA-BB 7070707021
S31-201 (NSC 74859)
NSC 74859 (S3I-201)
S3I-201 (NSC 74859)
S3I-201, 501919-59-1
Stat3 Inhibitor I, S3I-201
Stat3 Inhibitor VI, S3I-201
S3I201; NSC74859; NSC 74859; S3I 201
S3I201; NSC74859; NSC 74859;NSC-74859; S3I 201
OTAVA-BB 7070707021S31-201 (NSC 74859)，S3I-201
2-hydroxy-4-(2-(tosyloxy)acetaMido)benzoic acid
STAT3 Inhibitor VI, S3I-201 - CAS 501919-59-1 - Calbiochem
2-Hydroxy-4-[[[[(4-methylphenyl)sulfonyl]oxy]acetyl]amino]-benzoic acid
2-Hydroxy-4-[[2-[[(4-methylphenyl)sulfonyl]oxy]acetyl]amino]benzoic acid
Benzoic acid, 2-hydroxy-4-[[2-[[(4-methylphenyl)sulfonyl]oxy]acetyl]amino]-
2-Hydroxy-4-[[2-[[(4-methylphenyl)sulfonyl]oxy]acetyl]amino]benzoic acid NSC 74859(S3I-201) | [Molecular Formula]
C16H15NO7S | [MDL Number]
MFCD09907564 | [MOL File]
501919-59-1.mol | [Molecular Weight]
365.358 |
| Chemical Properties | Back Directory | [Melting point ]
>185oC (dec.) | [Boiling point ]
654.7±55.0 °C(Predicted) | [density ]
1.507 | [storage temp. ]
?20°C | [solubility ]
DMSO: >10mg/mL | [form ]
powder | [pka]
2.98±0.10(Predicted) | [color ]
white to beige | [InChI]
InChI=1S/C16H15NO7S/c1-10-2-5-12(6-3-10)25(22,23)24-9-15(19)17-11-4-7-13(16(20)21)14(18)8-11/h2-8,18H,9H2,1H3,(H,17,19)(H,20,21) | [InChIKey]
HWNUSGNZBAISFM-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=CC=C(NC(COS(C2=CC=C(C)C=C2)(=O)=O)=O)C=C1O |
| Hazard Information | Back Directory | [Uses]
A chemical probe inhibitor of STAT3 with an IC50 of 86 μM. | [Uses]
S2I-201 is a small molecule inhibitor that provides a pathway to rational combination therapies for Melanoma. | [Definition]
ChEBI: An amidobenzoic acid obtained by formal condensation of the carboxy group of [(4-methylbenzene-1-sulfonyl)oxy]acetic acid with the amino group of 4-amino-2-hydroxybenzoic acid. | [Biological Activity]
s3i-201 is a selective inhibitor of stat3 with ic50 value of 86 μm [1].in the in vitro stat3 dna-binding assay, s3i-201 showed potent inhibition of the stat3 dna-binding activity with an average ic50 of 86 μm. in the emsa assay, s3i-201 selectively inhibited stat3 dna-binding activity over that of stat1 and stat5. it suppressed the complex formation of stat1-stat3 and stat1-stat1 with ic50 values of 160 and > 300 μm, respectively. besides that, the unphosphorylated, inactive stat3 monomer was found to restore the stat3 dna-binding activity inhibited by s3i-201, suggesting that the inhibition was independent on the activation status. in nih 3t3/v-src fibroblasts, s3i-201 inhibited the constitutive activation of stat3 and reduced the ptyr-705 stat3 levels. moreover, s3i-201 was found to significantly induce apoptosis in cells with constitutively active stat3 at concentration of 30–100 μm. s3i-201 also reduced the expression of cyclin d1, bcl-xl and surviving in these cells [1]. | [Biochem/physiol Actions]
S3I-201 is a cell-permeable Stat3 inhibitor that binds to the Stat3-SH2 domain, prevents Stat3 phosphorylation/activation, dimerization, and DNA-binding. | [Synthesis]
A mixture of 7-aminosalicylic acid (102 mg, 0.67 mmol) with NaOH (27 mg, 0.67 mmol) in water (6 mL) was stirred at room temperature for 10 min until completely dissolved, using 7-aminosalicylic acid (102 mg, 0.67 mmol) as starting material. Na2CO3 (59 mg, 0.5561 mmol) was then added and the mixture was cooled to 0 °C. A solution of THF (2 mL) of 2-chloro-2-oxoethyl-4-methylbenzenesulfonate (200 mg, 0.8044 mmol) was quickly added, and the reaction system was gradually warmed to room temperature and stirred continuously for 2 hours. Upon completion of the reaction, the mixture was transferred to a partition funnel containing ether for phase separation. After the aqueous phase was washed with another portion of ether, the pH was adjusted to 1 by dropwise addition of 1N HCl solution and the product was subsequently extracted with ethyl acetate. The ethyl acetate phase was washed twice sequentially with 1N HCl solution, dried over Na2SO4, filtered and concentrated under reduced pressure to remove the solvent. The resulting light yellow solid was ground with chloroform to afford the target product 2-hydroxy-4-(2-(tolylsulfonyloxy)acetylamino)benzoic acid (155 mg, 63% yield) in white powder form. The product characterization data were as follows: 1H NMR (400 MHz, DMSO) δ 2.37 (3H, s, Me), 4.68 (2H, s, CH2), 6.93 (1H, d, J = 7.4 Hz, ArH), 7.17 (1H, s, ArH), 7.46 (2H, d, J = 6.8 Hz, ArH), 7.69 (1H, d, J = 7.4 Hz, ArH), 7.81 (2H, d, J = 6.8 Hz, ArH), 10.32 (1H, s, NH); 13C NMR (100.6 MHz, DMSO) δ 21.8, 68.0, 107.0, 110.7, 128.5, 130.9, 131.7, 132.7, 144.5, 146.0, 162.8, 164.8, 164.0, 166.0, 162.8, 164.8, 164.0, 166.0, 166.0, 164.0 162.8, 164.5, 172.2; MS (ES+) m/z 366.0 ([M + H]+, 100%), 388.0 ([M + Na]+, 50%); no signal detected in the negative ion mode. | [storage]
Store at -20°C,unstable in solution, ready to use. | [References]
[1] siddiquee k, zhang s, guida w c, et al. selective chemical probe inhibitor of stat3, identified through structure-based virtual screening, induces antitumor activity. proceedings of the national academy of sciences, 2007, 104(18): 7391-7396. |
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