6265-57-2

Basic information

• Product Name: N-(4-Benzothiazol-2-yl-phenyl)-acetamide
• Synonyms: N-(4-Benzothiazol-2-yl-phenyl)-acetamide
• CAS NO: 6265-57-2
• Molecular Formula: C₁₅H₁₂N₂OS
• Molecular Weight: 268.33
• Mol File: 6265-57-2.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Density: 1.311g/cm³
• Refractive Index: 1.704
• CAS DataBase Reference: N-(4-Benzothiazol-2-yl-phenyl)-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-Benzothiazol-2-yl-phenyl)-acetamide(6265-57-2)
• EPA Substance Registry System: N-(4-Benzothiazol-2-yl-phenyl)-acetamide(6265-57-2)

Safety Data

• Hazardous Substances Data: 6265-57-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H12N2OS/c1-10(18)16-12-8-6-11(7-9-12)15-17-13-4-2-3-5-14(13)19-15/h2-9H,1H3,(H,16,18)

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 622-50-4 4-Acetamido-1-iodobenzene 
• 122-85-0 para-acetamidobenzaldehyde 
• 137-07-5 2-amino-benzenethiol 
• 6278-73-5 2-(4-aminophenyl)benzothiazole 
• 150-13-0 4-amino-benzoic acid 
• 122-04-3 4-nitro-benzoyl chloride 
• 22868-34-4 2-(4-nitrophenyl)benzothiazole 
• 108-24-7 acetic anhydride 
• 16331-48-9 4-acetamidobenzoyl chloride 

Relevant articles and documents

Room temperature HFIP/Ag-promoted palladium-catalyzed C–H functionalization of benzothiazole with iodoarenes

A versatile synthetic protocol involving the room temperature direct arylation of benzothiazole with a wide variety of iodoarenes under Ag-promoted Pd-catalyzed conditions in HFIP as the reaction solvent has been presented. A sequential HFIP-promoted sele

Novel green procedure for the synthesis of 2-arylbenzothiazoles under microwave irradiation in Peg 200 or Peg 400

An improved green procedure for the synthesis of 2-aryl- and 2-hetarylbenzothiazoles by condensation of equivalent amounts of 2,2'-diaminodiphenyldisulfides or 2-aminothiophenols and various aromatic aldehydes in PEG 200/400 under microwave irradiation has been developed. This method allows the synthesis of 2-arylbenzothiazoles in high yields and with high purity regardless of the state of the starting compounds (liquid or solid) or the nature of the substituents in the aromatic ring. Copyright Taylor & Francis Group, LLC.

Antitumor benzothiazoles. 7. Synthesis of 2-(4- acylaminophenyl)benzothiazoles and investigations into the role of acetylation in the antitumor activities of the parent amines

2-(4-Aminophenyl)benzothiazoles display potent and selective antitumor activity against inter alia breast, ovarian, colon, and renal cell lines, but their mechanism of action, though yet to be defined, may be novel. Metabolism is suspected to play a central role in the mode of action of these benzothiazoles since drug uptake and biotransformation were observed in sensitive cell lines (e.g., breast MCF-7 and MDA 468 cells) in vitro, whereas insensitive cell lines (e.g., prostate PC 3 cells) showed negligible uptake and biotransformation. N-Acyl derivatives of the arylamines have been synthesized, and in vitro studies confirm N-acetylation and oxidation as the main metabolic transformations of 2-(4-aminophenyl)benzothiazoles. With the predominant process being dictated by the nature of the 3'-substituent. The prototype amine 3 underwent mainly N-acetylation in vitro, while 3'- substituted analogues 4 and 5 were primarily oxidized. N-Acetylation of 4 to 11 exerts a drastic dyschemotherapeutic effect in vitro, but acetylation of the halogeno congeners 5-7 gave acetylamines 12-14 which substantially retain selective antitumor activity. In vivo pharmacokinetic studies in rats confirmed rapid and exclusive N-acetylation of the 3'-methyl analogue 4, but less acetylation with the 3'-chloro analogue 5. Distinct expression patterns of N-acetyltransferase NAT1 and NAT2 have been demonstrated in our panel of cell lines.