Stattic

Base Information

• Chemical Name: Stattic
• CAS No.: 19983-44-9
• Molecular Formula: C₈H₅NO₄S
• Molecular Weight: 211.198
• Hs Code.: 2934999090
• European Community (EC) Number: 633-746-6
• DSSTox Substance ID: DTXSID70381575
• Nikkaji Number: J2.887.946F
• Wikidata: Q27159314
• Pharos Ligand ID: FTGMZ3DRBL7T
• ChEMBL ID: CHEMBL1337170
• Mol file: 19983-44-9.mol

Synonyms:6-Nitrobenzo[b]thiophene1,1-dioxide; Stattic

Chemical Property of Stattic

Chemical Property:

• Vapor Pressure: 3.04E-08mmHg at 25°C
• Melting Point: 184℃
• Boiling Point: 461.1°Cat760mmHg
• Flash Point: 232.6°C
• PSA: 88.34000
• Density: 1.621g/cm³
• LogP: 2.95680
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: >20mg/mL
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 210.99392881
• Heavy Atom Count: 14
• Complexity: 375

Purity/Quality:

99% ^*data from raw suppliers

Stattic ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC2=C1C=CS2(=O)=O)[N+](=O)[O-]
• Description: Stattic (19983-44-9) is a STAT3 inhibitor that inhibits binding of tyrosine-phosphorylated peptides to STAT3 SH2 domain and inhibiting STAT3 activation, dimerization and nuclear translocation.1 Displays selectivity over STAT1, STAT5, c-Myc/Max, Jun/Jun and Lck. Induces apoptosis in STAT3-dependent cancer cell lines. Alkyates four cysteine residues on STAT3.2 Exhibits potent antitumor activity.3 Protects against angiotensin II-induced vascular dysfunction and hypertension.4?Stattic is an extremely useful tool to probe involvement of STAT3 in cellular signaling.
• Uses: Stattic is a Stat3 inhibitor which exhibited potent anti-tumor and induced chemo- and radio-sensitivity in nasopharyngeal carcinoma. Stattic was used to study Stat3-mediated cell signaling in human lung carcinoma cells.5

Technology Process of Stattic

There total 8 articles about Stattic which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

benzothiophene-1,1-dioxide (825-44-5) → stattic (19983-44-9)

Guidance literature:

With nitric acid; In sulfuric acid; at 0 ℃; for 0.5h;

Reference yield:

6-nitro-1,1-dioxo-1λ6-benzo[b]thiophen-5-ylamine (858819-40-6) → stattic (19983-44-9)

Guidance literature:

With sulfuric acid; sodium nitrite; Behandeln der Reaktionsloesung mit Hypophosphorigsaeure und wenig Kupfer(II)-sulfat;

DOI:10.1021/ja01627a048

Reference yield:

N-(1,1-dioxo-1λ6-benzo[b]thiophen-5-yl)-acetamide (857473-99-5) → stattic (19983-44-9)

Guidance literature:

Multi-step reaction with 3 steps

1: nitric acid

2: acetic acid; concentrated aqueous hydrochloric acid

3: sulfuric acid; sodium nitrite / Behandeln der Reaktionsloesung mit Hypophosphorigsaeure und wenig Kupfer(II)-sulfat

With hydrogenchloride; sulfuric acid; nitric acid; acetic acid; sodium nitrite;

DOI:10.1021/ja01627a048

upstream raw materials:

benzothiophene-1,1-dioxide

6-nitro-1,1-dioxo-1λ⁶-benzo[b]thiophen-5-ylamine

nitric acid

Benzo[b]thiophene

Downstream raw materials:

2-carboxy-5-nitrobenzenesulfonic acid

1,1-dioxo-1H-1λ6-benzo[b]thiophen-6-ylamine

6-amino-2,3-dihydrobenzothiophene 1,1-dioxide

6-nitro-1,3-diphenyl-(3ar,8bc)-3a,8b-dihydro-1H-benzo[4,5]thieno[3,2-c]pyrazole 4,4-dioxide

Refernces

• 1、 An, Yuanlong,Du, Guoxin,Du, Weiwei,Gong, Qi,Hao, Feifei,He, Wei,He, Xiangdong,Jiang, Hualiang,Tong, Xiaochu,Wang, Minnan,Zhang, Donglei,Zheng, Mingyue. "Design, synthesis, and LFA-1/ICAM-1 antagonist activity evaluation of Lifitegrast analogues". . p. 555 - 579. Retrieved 2022/02/22.
• 2、 -. "PROTON PUMP INHIBITORS". . . Retrieved 2008/06/13.