91506-66-0

Upstream product

• 136-95-8 2-amino-benzthiazole 
• 874-60-2 4-methyl-benzoyl chloride 
• 651707-16-3 C₁₅H₁₃BrN₂OS 
• 104-87-0 4-methyl-benzaldehyde 
• 673450-74-3 C₁₅H₁₂N₂S 
• 99-94-5 p-Toluic acid 
• 201230-82-2 carbon monoxide 
• 624-31-7 4-tolyl iodide 
• 16794-68-6 4-methylbenzoyl isothiocyanate 
• 615-43-0 2-iodophenylamine 
• 1141-88-4 2-Aminophenyl disulfide 
• 1596412-59-7 C₁₅H₂₀N₂O₂S 
• 137-07-5 2-amino-benzenethiol 

Downstream Products

• 1428622-69-8 3-hydroxy-2-(2-(4-methylbenzoylimino)benzo[d]thiazol-3(2H)-yl)propionic acid 
• 1428622-70-1 methyl 3-hydroxy-2-(2-((4-methylbenzoyl)imino)benzo[d]thiazol-3(2H)-yl)propanoate 
• 1428622-75-6 2-(2-((4-methylbenzoyl)imino)benzo[d]thiazol-3(2H)-yl)-3-phenylpropionic acid 
• 91506-74-0 1-(2'-benzothiazolyl)-5-p-tolyltetrazole 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of some novel N'-(1,3-benzothiazol-2-yl)-arylamide derivatives as antibacterial agents

In the present work, we carried out hydroxybenzotriazole (HOBT) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCl)-mediated synthesis of new N'-(1,3-benzothiazol-2-yl)-arylamides C1-18 in high yields under relatively milder reaction conditions using dimethyl formamide as solvent. Synthesized compounds were characterized by FTIR, 1H-NMR, 13C-NMR and HRMS spectral data. The MIC values of synthesized compounds C1-18 were determined by the broth microdilution method using Mueller Hinton medium. Tested compounds showed variable activity against the tested Gram-positive and Gram-negative bacterial strains. Compounds C3, C5, C9, C13-15 and C17 exhibited promising activity against Staphylococcus aureus NCIM 5021 with MIC values in the range of 19.7–24.2?μM. Among all tested compounds, C13 possessing thiophene ring attached to the benzothiazole moiety via amide linkage exhibited maximum activity against S. aureus NCIM 5022 with MIC of 13.0?μM. Compound C13 showed maximum activity against S. aureus ATCC 43300 with MIC of 15.0?μM and exhibited bactericidal activity against this strain in minimum bactericidal concentration determination. This compound also eliminated S. aureus ATCC 43300 strain after 24-h exposure indicating its bactericidal activity. ADMET calculation showed favourable pharmacokinetic profile of synthesized compounds C1-18. Graphic abstract: [Figure not available: see fulltext.]

Synthesis of benzamide-benzothiazole conjugates via palladium-catalysed aminocarbonylation (hydrazinocarbonylation)

The palladium-catalysed aminocarbonylation of iodoarenes was investigated using 2-amino- and 2-hydrazinobenzothiazole as N-nucleophile. The reaction proved to be highly chemoselective in all cases: carboxamides and the corresponding carbohydrazides, obtained by the acylation at the nitrogen adjacent to the C-2 of the benzothiazole moiety, were obtained exclusively and isolated in moderate to high yields. Systematic investigation of the reaction conditions revealed that the reaction requires relatively high temperature (higher than 70 °C). The effect of the carbon monoxide pressure is different in the synthesis of the two types of products: while the carboxamide formation is favoured, the carbohydrazide formation is lowered by the increasing CO pressure.

On Water: Metal-Free Synthesis of Highly Functionalized Benzothiazolylidene from ortho-Haloanilines

An environmentally benign, transition-metal-free organic base promoted one-pot cascade synthesis of highly functionalized benzo[d]thiazol-2(3H)-ylidene benzamide in the presence of water was accomplished by three-component reaction of ortho-iodoanilines,

Access to Amide from Aldimine via Aerobic Oxidative Carbene Catalysis and LiCl as Cooperative Lewis Acid

Herein, an efficient route to amides from aldimines via aza-Breslow intermediates through aerobic oxidative carbene catalysis with LiCl as a cooperative Lewis acid is described. Many of the obtained N-heteroarylamides feature biological activity. Ambient

Facile synthesis of N-acyl 2-aminobenzothiazoles by NHC-catalyzed direct oxidative amidation of aldehydes

A mild, general, and high yielding synthesis of N-acyl 2-aminobenzothiazoles has been demonstrated by N-heterocyclic carbene (NHC)-organocatalyzed direct amidation of aldehydes with 2-aminobenzothiazoles proceeding via acyl azolium intermediates. The carbene generated from the triazolium salt under oxidative conditions was the key for the success of this reaction. The method was subsequently applied to the synthesis of various biologically important N-acyl 2-aminobenzothiazoles.

Synthesis of sulfur heterocycles via domino metal-mediated reactions

Two methodologies to access S-heterocycles and mixed N,S-heterocycles via metal-mediated domino reactions are described. One involves a cyclocarbopalladation/cross-coupling domino process and leads to benzene-fused five- or six-membered sulfur heterocycles with a stereo defined tetrasubstituted exocyclic double bond. The other consists in a three-component domino reaction between 2-aminophenyl disulfide, copper cyanide, and an electrophile to access N-substituted 2-amino benzothiazoles. Preliminary results in the use of the second method to access N-substituted 2-imino benzothiazoles are also reported.

Aerobic Copper-Mediated Domino Three-Component Approach to 2-Aminobenzothiazole Derivatives

An unprecedented three-component reaction involving a 2,2′-diaminodiaryl disulfide, copper cyanide, and an electrophile is described. This transformation is based on an oxidative copper-mediated S-cyanation as a key step and involves a cyanation/cyclization/acylation domino sequence enabling a rapid and efficient synthesis of diversely substituted 2-aminobenzothiazole derivatives. Notably, this reaction proceeds via an original mechanism involving an intermolecular migration of the acyl group.

PHENYLIMIDE-CONTAINING BENZOTHIAZOLE DERIVATIVE OF ITS SALT AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

Provided is a phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt, a process for the preparation thereof, and a pharmaceutical composition comprising the same. The phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt can selectively inhibit the protein-protein interaction between KRS and a laminin receptor (LR), thereby inhibiting migration of cancer cells. Therefore, the phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt may be usefully applied for preventing or treating the diseases associated with cancer cell metastasis.

PTSA catalyzed straightforward protocol for the synthesis of 2-(N-acyl)aminobenzimidazoles and 2-(N-acyl)aminobenzothiazoles in PEG

An efficient PTSA catalyzed synthesis of 2-(N-acyl)aminobenzimidazoles and 2-(N-acyl)aminobenzothiazoles has been described using S-ethylated-N- acylthioureas as substrates and polyethylene glycol as solvent.

Novel solid-phase parallel synthesis of N-substituted-2-aminobenzo [d]thiazole derivatives via cyclization reactions of 2-iodophenyl thiourea intermediate resin

A novel solid-phase methodology has been developed for the synthesis of N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo[d]thiazole resins 5 by cyclization reaction of 2-iodophenyl thiourea resin 3. The resin-bound 2-iodophenyl thiourea 3 is produced by addition of 2-iodophenyl isothiocyanate 2 to the amine-terminated linker amide resin 1. These core skeleton 2-aminobenzo[d]thiazole resins 5 undergo functionalization reactions with various electrophiles, such as alkyl halides, acid chlorides, and sulfonyl chlorides to generate N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole resins 6, 7, and 8, respectively. Finally, N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives 9, 10, and 11 are then generated in good yields and purities by cleavage of the respective resins 6, 7, and 8 using trifluoroacetic acid (TFA) in dichloromethane (DCM).