69791-46-4

Upstream product

• 136-95-8 2-amino-benzthiazole 
• 104-88-1 4-chlorobenzaldehyde 
• 62-53-3 aniline 

Downstream Products

• 69791-54-4 3-benzothiazol-2-yl-2-(4-chloro-phenyl)-thiazolidin-4-one 
• 121060-54-6 methyl [2-(4-chlorophenyl)imidazo[2,1-b][1,3]benzothiazol-3-yl]acetate 
• 35353-18-5 N-(4-chlorobenzoyl)-2-aminobenzo[d]thiazole 

Relevant academic research and scientific papers

Organocatalytic Asymmetric Synthesis of Benzothiazolopyrimidines via [4 + 2] Cyclization of 2-Benzothiazolimines and Aldehydes

We report the direct asymmetric synthesis of pyrimido[2,1-b]benzothiazoles using a commercially available chiral amine catalyst. A variety of 2-benzothiazolimines and aldehydes were well tolerated under the reaction conditions and generated the corresponding products in 81-99% yields with excellent diastereoselectivities and enantioselectivities (up to >20:1 dr, 99% ee). Furthermore, the products could be easily converted to other useful chiral building blocks.

Development of 1,3-thiazole analogues of imidazopyridines as potent positive allosteric modulators of GABAA receptors

Structure–activity relationship studies were conducted in the search for 1,3-thiazole isosteric analogs of imidazopyridine drugs (Zolpidem, Alpidem). Three series of novel γ-aminobutyric acid receptor (GABAAR) ligands belonging to imidazo[2,1-b]thiazoles, imidazo[2,1-b][1,3,4]thiadiazoles, and benzo[d]imidazo[2,1-b]thiazoles were synthesized and characterized as active agents against GABAAR benzodiazepine-binding site. In each of these series, potent compounds were discovered using a radioligand competition binding assay. The functional properties of highest-affinity compounds 28 and 37 as GABAAR positive allosteric modulators (PAMs) were determined by electrophysiological measurements. In vivo studies on zebrafish demonstrated their potential for the further development of anxiolytics. Using the OECD “Fish, Acute Toxicity Test” active compounds were found safe and non-toxic. Structural bases for activity of benzo[d]imidazo[2,1-b]thiazoles were proposed using molecular docking studies. The isosteric replacement of the pyridine nuclei by 1,3-thiazole, 1,3,4-thiadiazole, or 1,3-benzothiazole in the ring-fused imidazole class of GABAAR PAMs was shown to be promising for the development of novel hypnotics, anxiolytics, anticonvulsants, and sedatives drug-candidates.

Organocatalytic asymmetric [4+2] cyclization of 2-benzothiazolimines with azlactones: Access to chiral benzothiazolopyrimidine derivatives

An organocatalytic asymmetric domino Mannich/cyclization reaction between 2-benzothiazolimines with azlactones has been successfully developed. With the bifunctional squaramide catalyst, this formal [4+2] cyclization occurs with good to high yields and excellent stereoselectivities (up to 99% ee, >20?:?1 dr), providing an efficient and mild access to chiral benzothiazolopyrimidines bearing adjacent tertiary and quaternary stereogenic centers.

Benzothiazole analogues: Synthesis, characterization, MO calculations with PM6 and DFT, in silico studies and in vitro antimalarial as DHFR inhibitors and antimicrobial activities

Benzothiazole analogues are of interest due to their potential activity against malarial and microbial infections. In search of suitable antimicrobial and antimalarial agents, we report here the synthesis, characterization and biological activities of benzothiazole analogues (J 1-J 10). The molecules were characterized by IR, Mass, 1H NMR, 13C NMR and elemental analysis. The in vitro antimicrobial activity was investigated against pathogenic strains; the results were explained with the help of DFT and PM6 molecular orbital calculations. In vitro cytotoxicity and genotoxicity of the molecules were studied against S. pombe cells. In vitro antimalarial activity was studied. The active compounds J 1, J 2, J 3, J 5 and J 6 were further evaluated for enzyme inhibition efficacy against the receptor Pf-DHFR, computational and in vitro studies were carried out to examine their candidatures as lead dihydrofolate reductase inhibitors.

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

Synthesis of Imidazo[2,1-b]thiazoles via Copper-Catalyzed A3-Coupling in Batch and Continuous Flow

A straightforward method for the synthesis of functionalized imidazo[2,1-b]thiazoles starting from benzaldehydes, 2-aminothiazoles, and alkynes under copper(I,II) catalysis was developed. The protocol allows the construction of a variety of aryl-substituted imidazo[2,1-b]benzothiazoles, -[2,1-b]thiazoles, and -[2,1-b][1,3,4]thiadiazoles. The reactions were easy to perform affording most of the desired products in 33-93% yields. The intensification of the process in a continuous-flow reactor increases the products' yields up to quantitative.

Ultrasound-assisted one-pot synthesis of bis-azetidinones in the presence of zeolite

Sonochemical method is an innovative task for the sustainable chemical research industry. In this work, an attempt was made to synthesize bis-azetidin-2-ones (2a, 2b, 2c, 2d, 2e, 2f, 2g, 2h, 2i, 2j) by Staudinger reaction ([2 + 2] ketene-imine cycloadditi

Three-component synthesis of 4-amino-2-aryl-2H-pyrimido-[1,2-b][1,3] benzazole-3-carbonitriles and 4H-pyrimido-[2,1-b][1,3]benzazoles in the presence of magnesium oxide and 12-tungstophosphoric acid as catalysts

A simple and convenient approach was suggested for the synthesis of 4-amino-2-aryl-2H-pyrimido[1,2-b][1,3]benzimidazole-3-carbonitriles or -benzothiazole-3-carbonitriles through a three-component reaction of 2-aminobenzimidazole or 2-aminobenzothiazole, a

Spectral investigation of the activities of amino substituted bases

Three new series of biologically active amino substituted Schiff bases with general formula, R1N=CHR2. Here R1 = 2-amino-benzthiazole, 4-amino-salicylic acid and 4-aminophenol. R 2=4-chloro-benzaldehyde, 2-chloro-benzaldehyde, salicylaldehyde, vanillin and benzaldehyde were synthesized by the reaction of three different amino substituted compounds and substituted aldehydes in ethanol. Such compounds were characterized by different physico-chemical techniques like, melting point, elemental analysis, multinuclear nmr (1H, 13C). The free ligands and their metal complexes have been screened for their in vitro biological activities against bacteria, fungi and yeast. The metal complexes show more potent activities compared with Schiff base ligands.

Synthesis, spectral investigation (1H, 13C) of new (N, O and S based) schiff bases and evaluation of their antimicrobial activities

Three new series of biologically active amino substituted Schiff bases (1-12) with general formula, R1N=CHR2 (R1 = 2-amino-benzthiazole, 4-amino-salicylic acid and 4-aminophenol; R2 = benzaldehyde, 2-chloro-benzaldehyde, 4-chloro-benzaldehyde, salicylaldehyde and vanillin) were synthesized by the reaction of three different amino substituted compounds and substituted aldehydes in ethanol. The synthesized compounds were characterized by different physico-chemical techniques like, melting point, elemental analysis, multinuclear nmr (1H, 13C). The compounds were subjected for bioassay screening and showed promising antibacterial and antifungal activities using Amoxicillin and Ciprofloxacin as standard drugs.