260443-89-8

Basic information

• Product Name: NSC-703786
• Synonyms: 4-(5-Fluoro-2-benzothiazolyl)-2-methyl-benzenamine;5F203;5F-203;NSC-703786;5-fluoro 203;4-(5-fluoro-1,3-benzothiazol-2-yl)-2-methylaniline
• CAS NO: 260443-89-8
• Molecular Formula: C₁₄H₁₁FN₂S
• Molecular Weight: 258.3139432
• Mol File: 260443-89-8.mol
• Article Data: 8

Chemical Properties

• Appearance: white to beige/
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble20mg/mL, clear
• CAS DataBase Reference: NSC-703786(CAS DataBase Reference)
• NIST Chemistry Reference: NSC-703786(260443-89-8)
• EPA Substance Registry System: NSC-703786(260443-89-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 260443-89-8(Hazardous Substances Data)

Usage

Uses

5-Fluoro 203 is a cytotoxic agent which actiates AhR signaling, inducing transcription of CYP1A1 which leads to the formation of DNA adducts and cell cycle arrest.

Upstream product

• 3113-71-1 3-methyl-4-nitrobenzoic acid 
• 343975-42-8 N-(3-fluoro-phenyl)-3-methyl-4-nitro-thiobenzamide 
• 343975-60-0 N-(2-bromo-5-fluorophenyl)-3-methyl-4-nitrobenzamide 
• 260444-01-7 N-(2-bromo-5-fluorophenyl)-3-methyl-4-nitrobenzothioamide 
• 35675-46-8 3-methyl-4-nitro-benzoyl chloride 
• 1003-99-2 2-bromo-5-fluoroaniline 
• 260443-96-7 5-fluoro-2-(3-methyl-4-nitrophenyl)benzothiazole 

Relevant articles and documents

Recyclable copper-catalyzed cyclization of o-haloanilides and metal sulfides: An efficient and practical access to substituted benzothiazoles

An efficient heterogeneous copper-catalyzed cyclization of o-haloanilides and metal sulfides has been achieved via the C–S coupling in DMF at 80 or 140 °C in the existence of an MCM-41-bound NHC-Cu(I) catalyst and then intramolecular condensation, delivering a wide range of substituted benzothiazoles in mostly good to high yields. This new MCM-41-NHC-CuI complex can facilely be obtained by a two-step procedure starting from easily accessible and inexpensive reagents and reused more than seven times without any significant loss of its catalytic efficiency. The present protocol has been successfully applied to the gram-scale synthesis of two antitumor agents 5F203 and PMX 610.

Bioactivation of fluorinated 2-aryl-benzothiazole antitumor molecules by human cytochrome P450s 1A1 and 2W1 and deactivation by cytochrome P450 2S1

Both 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (5F 203) and 5-fluoro-2-(3,4-dimethoxyphenyl)-benzothiazole (GW 610) contain the benzothiazole pharmacophore and possess potent and selective in vitro antitumor properties. Prior studies suggested the involvement of cytochrome P450 (P450) 1A1 and 2W1-mediated bioactivation in the antitumor activities and P450 2S1-mediated deactivation of 5F 203 and GW 610. In the present study, the biotransformation pathways of 5F 203 and GW 610 by P450s 1A1, 2W1, and 2S1 were investigated, and the catalytic parameters of P450 1A1- and 2W1-catalyzed oxidation were determined in steady-state kinetic studies. The oxidations of 5F 203 catalyzed by P450s 1A1 and 2W1 yielded different products, and the formation of a hydroxylamine was observed for the first time in the latter process. Liquid chromatography-mass spectrometry (LC-MS) analysis with the synthetic hydroxylamine and also a P450 2W1/5F 203 incubation mixture indicated the formation of dGuo adduct via a putative nitrenium intermediate. P450 2W1-catalyzed oxidation of GW 610 was 5-fold more efficient than the P450 1A1-catalyzed reaction. GW 610 underwent a two-step oxidation process catalyzed by P450 1A1 or 2W1: a regiospecific O-demethylation and a further hydroxylation. Glutathione (GSH) conjugates of 5F 203 and GW 610, presumably through a quninoneimine and a 1,2-quinone intermediate, respectively, were detected. These results demonstrate that human P450s 1A1 and 2W1 mediate 5F 203 and GW 610 bioactivation to reactive intermediates and lead to GSH conjugates and a dGuo adduct, which may account for the antitumor activities of 5F 203 and GW 610 and also be involved in cell toxicity. P450 2S1 can catalyze the reduction of the hydroxylamine to the amine 5F 203 under anaerobic conditions and, to a lesser extent, under aerobic conditions, thus attenuating the anticancer activity.

Metabolically stabilized benzothiazoles for imaging of amyloid plaques

Six new N-11C-labeled aminophenylbenzothiazoles substituted with fluorine in different positions have been synthesized and evaluated as amyloid-β binding ligands. Our structure-property relationship studies show that the substitution pattern of