19983-44-9

Basic information

• Product Name: Stattic
• Synonyms: 6-NITRO-1H-1LAMBDA6-BENZO[B]THIOPHENE-1,1-DIONE;AKOS 1001;BUTTPARK 97\04-73;6-Nitro-1-benzothiophene 1,1-dioxide;1,1-DIOXO-6-NITROBENZO(B)THIOPHENE;6-Nitrobenzo[b]thiophene-1,1-dioxide, Stat three inhibitory compound;Stattic;6-Nitrobenzo[b]thiophene1,1-dioxide
• CAS NO: 19983-44-9
• Molecular Formula: C₈H₅NO₄S
• Molecular Weight: 211.19
• Product Categories: JAK/STAT;Inhibitors;JAK;STAT
• Mol File: 19983-44-9.mol

Chemical Properties

• Melting Point: 184℃
• Boiling Point: 461.1°Cat760mmHg
• Flash Point: 232.6°C
• Appearance: white to beige/
• Density: 1.621g/cm³
• Vapor Pressure: 3.04E-08mmHg at 25°C
• Refractive Index: 1.671
• Storage Temp.: Store at +4°C
• Solubility: DMSO: >20mg/mL
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
• CAS DataBase Reference: Stattic(CAS DataBase Reference)
• NIST Chemistry Reference: Stattic(19983-44-9)
• EPA Substance Registry System: Stattic(19983-44-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 19983-44-9(Hazardous Substances Data)

Usage

Uses

Used in Cancer Research and Treatment:
Stattic is used as a potent anti-tumor agent for inducing chemoand radio-sensitivity in nasopharyngeal carcinoma. It is particularly effective in modulating the STAT3 signaling pathway, which plays a crucial role in the development and progression of various cancers.
Used in Cellular Signaling Studies:
Stattic is used as a research tool to study STAT3-mediated cell signaling in human lung carcinoma cells. By inhibiting STAT3 activation, dimerization, and nuclear translocation, it helps researchers understand the underlying mechanisms of STAT3 involvement in cellular processes and its potential as a therapeutic target.
Used in Drug Development:
Stattic is used in the development of novel drug delivery systems to enhance its applications and efficacy against cancer cells. Researchers are exploring the use of various organic and metallic nanoparticles as carriers for Stattic delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes in cancer treatment.

Biological Activity

Small molecule inhibitor of STAT3. Inhibits binding of tyrosine-phosphorylated peptide motifs to STAT3 SH2 domain and inhibits STAT3 activation, dimerization and nuclear translocation. Displays selectivity over STAT1, STAT5, c-Myc/Max, Jun/Jun and Lck. Induces apoptosis in STAT3-dependent cancer cell lines.

Biochem/physiol Actions

Stattic (Stat3 three inhibitory compound) alters the SH2 domain of Stat3 and indirectly inhibits with phosphopeptide binding. It is readily transported across the cell membrane compared to other phosphopeptides.2 Stattic induces increased formation of ROS and negatively affects the cardiomyocyte mitochondrial function,3 and sensitizes nasopharyngeal carcinoma cells to chemoradiotherapy.4

References

1) Schust et al. (2006), Stattic: a small molecule inhibitor of STAT3 activation and dimerization; Chem. Biol., 13 1235 2) Heidelberger et al. (2013), Investigation of the protein alkylation sites of the STAT3:STAT3 inhibitor Stattic by mass spectrometry; Bioorg. Med. Chem. Lett., 23 4719 3) Pan et al. (2013), Stat3 inhibitor Stattic exhibits potent anti-tumor activity and induces chemo- and radio-sensitivity in nasopharyngeal carcinoma; PLoS One, 8(1) e54565 4) Johnson et al. (2013), Small-molecules inhibitors of signal transducer and activator of transcription 3 protect against angiotensin II-induced vascular dysfunction and hypertension; Hypertension, 61 437

InChI:InChI=1/C8H5NO4S/c10-9(11)7-2-1-6-3-4-14(12,13)8(6)5-7/h1-5H

Upstream product

• 825-44-5 benzothiophene-1,1-dioxide 
• 7697-37-2 nitric acid 
• 95-15-8 Benzo[b]thiophene 
• 857473-99-5 N-(1,1-dioxo-1λ⁶-benzo[b]thiophen-5-yl)-acetamide 
• 51956-01-5 5-aminobenzo[b]thiophene 1,1-dioxide 
• 850855-54-8 N-(6-nitro-1,1-dioxo-1λ⁶-benzo[b]thiophen-5-yl)-acetamide 
• 858819-40-6 6-nitro-1,1-dioxo-1λ⁶-benzo[b]thiophen-5-ylamine 

Downstream Products

• 22952-26-7 2-carboxy-5-nitrobenzenesulfonic acid 
• 20503-40-6 1,1-dioxo-1H-1λ6-benzo[b]thiophen-6-ylamine 
• 20503-39-3 6-amino-2,3-dihydrobenzothiophene 1,1-dioxide 
• 54249-04-6 6-nitro-1,3-diphenyl-(3ar,8bc)-3a,8b-dihydro-1H-benzo[4,5]thieno[3,2-c]pyrazole 4,4-dioxide 
• 117081-10-4 8-Ethyl-5,8-dihydro-5-oxo-thieno<3,2-g>chinolin-6-carbonsaeure 
• 1520073-15-7 4-[(1R)-2-((6-[4-(1,1-dioxido-2,3-dihydrobenzothiophen-6-yl)butoxy]hexyl)amino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol acetate salt 

Relevant articles and documents

Synthesis and cytotoxic activity of lipophilic sulphonamide derivatives of the benzo[b]thiophene 1,1-dioxide

In the search of new compounds with antineoplastic activity, we have analysed the effect of several structural modifications on the nucleus 6-benzo[b]thiophenesulphonamide 1,1-dioxide on its cytotoxic activity on tumour cells. Lipophilic substituents on t

Design, synthesis, and LFA-1/ICAM-1 antagonist activity evaluation of Lifitegrast analogues

The interaction between Lymphocyte function-associated antigen 1 (LFA-1) and intercellular-adhesion molecule-1 (ICAM-1) plays important roles in the cell-mediated immune response and inflammation associated with dry eye disease. LFA-1/ICAM-1 antagonists can be used for the treatment of dry eye disease, such as Lifitegrast which has been approved by the FDA in 2016 as a new drug for the treatment of dry eye disease. In this study, we designed and synthesized some new structure compounds that are analogues to Lifitegrast, and their biological activities were evaluated by in vitro cell-based assay and also by in vivo mouse dry eye model. Our results demonstrated that one of these analogues of Lifitegrast (compound 1b) showed good LFA-1/ICAM-1 antagonist activity in in vitro assay; meanwhile, it also significantly reduced ocular surface epithelial cells damage, increased goblet cell density in dry eye mouse and highly improved the symptoms of dry eye mouse. [Figure not available: see fulltext.]

Proton pump inhibitors

A proton pump inhibitor containing a compound represented by the formula (I) wherein X and Y are the same or different and each is a bond or a spacer having 1 to 20 carbon atoms in the main chain, R 1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R 2 , R 3 and R 4 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted thienyl group, an optionally substituted benzo[b]thienyl group, an optionally substituted furyl group, an optionally substituted pyridyl group, an optionally substituted pyrazolyl group, an optionally substituted pyrimidinyl group, an acyl group, a halogen atom, a cyano group or a nitro group, R 5 and R 6 are the same or different and each is a hydrogen atom or an optionally substituted hydrocarbon group, which has a superior proton pump action and shows an antiulcer activity and the like after conversion to a proton pump inhibitor in the body, or a salt thereof. or a prodrug thereof is provided.

PROTON PUMP INHIBITORS

A proton pump inhibitor containing a compound represented by the formula (I) wherein X and Y are the same or different and each is a bond or a spacer having 1 to 20 carbon atoms in the main chain, R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R2, R3 and R4 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted thienyl group, an optionally substituted benzo[b]thienyl group, an optionally substituted furyl group, an optionally substituted pyridyl group, an optionally substituted pyrazolyl group, an optionally substituted pyrimidinyl group, an acyl group, a halogen atom, a cyano group or a nitro group, R5 and R6 are the same or different and each is a hydrogen atom or an optionally substituted hydrocarbon group, which has a superior proton pump action and shows an antiulcer activity and the like after conversion to a proton pump inhibitor in the body, or a salt thereof. or a prodrug thereof is provided.

PROTON PUMP INHIBITORS

Proton pump inhibitors which have excellent proton pumping activity and which can be converted in vivo into proton pump inhibitors to exhibit antiulcer effect and so on, containing compounds represented by the general formula (I) or salts thereof or prodrugs of the same: (I) wherein X and Y are each independently a free valency or a spacer whose main chain has 1 to 20 carbon atoms; R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; R2, R3 and R4 are each independently hydrogen, an optionally substituted hydrocarbon group, optionally substituted thienyl, optionally substituted benzo[b]thienyl, optionally substituted furyl, optionally substituted pyridyl, optionally substituted pyrazolyl, optionally substituted pyrimidinyl, acyl, halogeno, cyano, or nitro; and R5 and R6 are each independently hydrogen or an optionally substituted hydrocarbon group.