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501919-59-1 molecular structure
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2-hydroxy-4-{2-[(4-methylbenzenesulfonyl)oxy]acetamido}benzoic acid

ChemBase ID: 72549
Molecular Formular: C16H15NO7S
Molecular Mass: 365.3578
Monoisotopic Mass: 365.05692283
SMILES and InChIs

SMILES:
c1(ccc(cc1)S(=O)(=O)OCC(=O)Nc1ccc(c(c1)O)C(=O)O)C
Canonical SMILES:
O=C(Nc1ccc(c(c1)O)C(=O)O)COS(=O)(=O)c1ccc(cc1)C
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

Cite this record

CBID:72549 http://www.chembase.cn/molecule-72549.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-hydroxy-4-{2-[(4-methylbenzenesulfonyl)oxy]acetamido}benzoic acid
IUPAC Traditional name
2-hydroxy-4-{2-[(4-methylbenzenesulfonyl)oxy]acetamido}benzoic acid
Synonyms
NSC 74859
S31-201
CAS Number
501919-59-1
PubChem SID
162037474
PubChem CID
252682

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Selleck Chemicals
S1155 external link Add to cart Please log in.
Data Source Data ID
PubChem 252682 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 2.872063  H Acceptors
H Donor LogD (pH = 5.5) 0.384205 
LogD (pH = 7.4) -0.5261129  Log P 2.9618375 
Molar Refractivity 89.803 cm3 Polarizability 34.471756 Å3
Polar Surface Area 130.0 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Storage Condition
-20°C expand Show data source
Target
STAT expand Show data source
Salt Data
Free Base expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S1155 external link
Research Area
Description Cancer
Biological Activity
Description S3I-201 (NSC 74859) is a Stat3 inhibitor with IC50 of 86 μM.
Targets Stat3
IC50 86 μM [1]
In Vitro S3I-201 inhibits growth and induces apoptosis preferentially in tumor cells that contain persistently activated Stat3 by inhibiting Stat3·Stat3 complex formation and Stat3 DNA-binding and transcriptional activitie. Moreover, S3I-201 also inhibits the expression of the Stat3-regulated genes encoding cyclin D1, Bcl-xL, and survivin. [1] S3I-201 inhibits breast carcinoma MDA-MB-435, MDA-MB-453 and MDA-MB-231 cell lines with IC50 of 100 μM. In addition, the cells with impaired TGF-β signaling are four times as sensitive to the STAT3 inhibitor S3I-201. [2] A recent study shows that S3I-201 potentiates the antiproliferative effect of cetuximab in HepG2 and Huh-7 cells via the STAT3 signalling pathway. [3]
In Vivo S3I-201 (5 mg/kg, i.v. every 2 or every 3 days) shows the antitumor efficacy in mouse models with human breast tumor xenografts that harbor constitutively active Stat3. [1] S3I-201 treatment reduces Varicella-zoster virus (VZV) replication on the basis of the bioluminescence signal and the number of positive skin xenografts compared with DMSO-treated mice by inhibiting STAT3 phosphorylation. [4]
Clinical Trials
Features S3I-201 is a chemical probe inhibitor of Stat3 activity.
Protocol
Kinase Assay [1]
In vitro Stat3 DNA-binding assay and EMSA analysis Briefly, 100 mL of biotinyl-e-Ac-EPQpYEEIEL-OH (in 50 mM Tris/150 mM NaCl, pH 7.5) is added to each well of streptavidin-coated 96-well microtiter plates and incubated with shaking at 4 °C overnight. Then plates are rinsed with PBS/Tween 20 and then two times with 200 mL of BSA-T-PBS (0.2% BSA/0.1% Tween 20/PBS). Then 50 mL of Lck-SH2-GST fusion protein (6.4 ng/ml in BSA-T-PBS) is added to each well of the 96-well plate in the presence and absence of 50 mL of S3I-201 (for 30 and 100 mM final concentrations), and the plate is shaken at room temperature for 4 hours. After solutions are removed, each well is rinsed four times with BSA-T-PBS (200 mL), and 100 mL of polyclonal rabbit anti-GST antibody (100 ng/mL in BSA-T-PBS) is added to each well and incubated at 4 °C overnight. After washing with BSA-T-PBS, 100 mL of 200 ng/mL BSA-T-PBS horseradish peroxidase-conjugated mouse anti-rabbit antibody is added to each well and incubated for 45 minutes at room temperature. After four washing steps with BSA-T-PBS and three washing steps with PBS-T, 100 mL of peroxidase substrate is added to each well and incubated for 5-15 minutes. The peroxidase reaction is stopped by adding 100 mL of 1 M sulfuric acid solution, and absorbance is read at 450 nm with an ELISA plate reader.
Cell Assay [2]
Cell Lines MDA-MB-435, MDA-MB-453 and MDA-MB-231 cells lines
Concentrations ~ 250 μM
Incubation Time 72 hours
Methods The MTT assay is based on the conversion of the yellow tetrazolium salt MTT to purple formazan crystals by metabolically active cells. The MTT assay provides a quantitative determination of viable cells. Cells are seeded in 96-well microplates in complete culture medium in the absence or presence of increasing serial dosages of S3I-201 as indicated. At 72 hours after culture, the number of viable cells is measured by adding 100 μL/well of 2 mg/mL MTT solution. After 2 hours, the medium is removed, and the formazan crystals are dissolved by adding 100 μL dimethylsulfoxide per well. The absorbance is read at 590 nm with an enzyme-linked immunosorbent assay reader. Each treatment point is performed in 10 wells or sextuplicate.
Animal Study [1]
Animal Models Human breast cancer MDA-MB-231 cells are injected s.c. into the left flank of athymic nu/nu mice.
Formulation S3I-201 is formulated in DMSO.
Doses ≤5 mg/kg
Administration Administered via i.v.
References
[1] Siddiquee K, et al. Proc Natl Acad Sci U S A, 2007, 104(18), 7391-7396.
[2] Lin L, et al. Oncogene, 2009, 28(7), 961-972.
[3] Chen W, et al. Liver Int, 2012, 32(1), 70-77.
[4] Sen N, et al. Proc Natl Acad Sci U S A, 2012, 109(2), 600-605.

PATENTS

PATENTS

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INTERNET

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