Benzothiazole, 2-(3,4-dimethoxyphenyl)-5-fluoro-

Base Information

• Chemical Name: Benzothiazole, 2-(3,4-dimethoxyphenyl)-5-fluoro-
• CAS No.: 872726-44-8
• Molecular Formula: C15H12FNO2S
• Molecular Weight: 289.33
• UNII: X3XWA9LQ3Q
• DSSTox Substance ID: DTXSID60236247
• Nikkaji Number: J2.725.682A
• Wikidata: Q27293529
• ChEMBL ID: CHEMBL373251
• Mol file: 872726-44-8.mol

Synonyms:2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole;GW 610;GW-610;GW610 compound;NSC 721648;NSC-721648;NSC721648;PMX 610;PMX-610;PMX610

Chemical Property of Benzothiazole, 2-(3,4-dimethoxyphenyl)-5-fluoro-

Chemical Property:

• PSA: 59.59000
• LogP: 4.11960
• Storage Temp.: +2C to +8C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 289.05727796
• Heavy Atom Count: 20
• Complexity: 333

Purity/Quality:

97% ^*data from raw suppliers

GW610 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2=NC3=C(S2)C=CC(=C3)F)OC
• Description: GW 610 is an antitumor benzothiazole that shows growth-inhibitory activity against several cancer cell lines. In MCF-7 and MDA 468 human cancer cell lines, potent antiproliferative activity (growth inhibition (GI50) < 0.1 nM) was observed. Potent and selective activity was also observed in the NCI 60 human cancer cell line panel. In contrast with previously reported 2-(4-aminophenyl)benzothiazoles, GW 610 is not reliant on induction of cytochrome P 1A1 (CYP1A1) expression for antitumor activity.
• Uses: GW 610 is a fluorinated 2-arylbenzothiazole and potential antitumor drug, which shows potent and selective inhibitory activity against breast, lung, and colon cancer cell lines. Studies suggest that the species-specific partial agonism of the aryl hydrocarbon receptor shown by GW 610 plays an important role in its anti-proliferative activity.

Technology Process of Benzothiazole, 2-(3,4-dimethoxyphenyl)-5-fluoro-

There total 21 articles about Benzothiazole, 2-(3,4-dimethoxyphenyl)-5-fluoro- 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: 93.0%

N-(2-bromo-5-fluorophenyl)-3,4-dimethoxybenzothioamide → NSC 721648 (872726-44-8)

Guidance literature:

With sodium phosphate; In dimethyl sulfoxide; at 20 ℃; for 10h; Inert atmosphere; Irradiation;

DOI:10.1021/acs.orglett.1c00235

Reference yield: 90.0%

3,4-dimethoxy-benzaldehyde (120-14-9) + 4,4'-difluoro-2,2'-diaminodiphenyl disulfide (224791-45-1) → NSC 721648 (872726-44-8)

Guidance literature:

With toluene-4-sulfonic acid; triphenylphosphine; for 15h; Heating;

DOI:10.1016/j.bmc.2006.08.026

Reference yield: 87.0%

3,4-dimethoxy-benzaldehyde (120-14-9) + 5-fluoro-2-iodoaniline (255724-71-1) → NSC 721648 (872726-44-8)

Guidance literature:

With potassium sulfide; acetic acid; In dimethyl sulfoxide; at 110 ℃;

upstream raw materials:

3,4-dimethoxy-benzaldehyde

4,4'-difluoro-2,2'-diaminodiphenyl disulfide

meta-fluoroaniline

2-amino-5-fluorobenzothiazole