64951-05-9

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl imidazo[2,1-b][1,3]benzothiazole-2-carboxylate is used as a building block for the synthesis of various pharmaceutical compounds due to its potential biological activities and unique molecular structure. It contributes to the development of new drugs with anti-inflammatory and antitumor properties.
Used in Materials Science:
In the field of materials science, ethyl imidazo[2,1-b][1,3]benzothiazole-2-carboxylate is utilized for the synthesis of organic materials, leveraging its structural properties to create novel materials with specific characteristics and applications.

InChI:InChI=1/C12H10N2O2S/c1-2-16-11(15)8-7-14-9-5-3-4-6-10(9)17-12(14)13-8/h3-7H,2H2,1H3

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 2999-46-4 Ethyl isocyanoacetate 
• 70-23-5 ethyl Bromopyruvate 
• 21224-16-8 2-amino-6-ethylbenzo[d]thiazole 
• 136-95-8 2-amino-benzthiazole 

Downstream Products

• 64951-09-3 imidazo<2,1-b>benzothiazole-2-carboxylic acid 
• 114094-98-3 Benzo[d]imidazo[2,1-b]thiazole-2-carboxylic acid cyclohexyl ester 
• 114094-91-6 Benzo[d]imidazo[2,1-b]thiazol-2-yl-phenyl-methanone 
• 623906-22-9 4-nitrobenzyl 6-[(acetyloxy)(imidazo[2,1-b][1,3]benzothiazol-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicylco[3.2.0]hept-2-ene-2-carboxylate 
• 114095-04-4 2-formylimidazo[2,1-b]benzothiazole 
• 114095-02-2 imidazo[2,1-b]benzothiazole-2-methanol 

Relevant academic research and scientific papers

Copper-Promoted Cycloaddition of α-Methylenyl Isocyanides with Benzothiazoles: Tunable Access to Benzo[d]imidazothiazoles

A tunable route to both isomers of benzo[d]imidazothiazole has been developed through copper-promoted cycloaddition of α-methylenyl isocyanides with benzothiazoles. When the C2 position of benzothiazole is linked to a C-H or C-C bond, benzo[d]imidazo[2,1-

A new fluorescent probe based on imidazole[2,1-b]benzothiazole for sensitive and selective detection of Cu2+

A simple fluorescent chemosensor WS1 (N'-[(Z)-1H-indazol-3-ylmethylidene]imidazo [2,1-b] [1,3]benzothiazole-2-carbohydrazide) based on imidazole [2,1-b]benzothiazole was designed and synthesized. The probe showed specific recognition towards Cu2+ through colorimetric and “turn-off” fluorescence response in MeOH/H2O (9:1 V/V) buffer solution (10 mM Tris, pH = 7.4) with detection limit of 4.32 × 10?8 M. In addition, WS1 was a reversible fluorescence probe for the detection of Cu2+, the fluorescence intensity recovered to the similar state of free WS1 as PPi was added. And it showed a favorable potency for actual water monitoring. The proposed binding mode of WS1 with Cu2+ was verified by DFT calculation using Gaussian 09.

On water catalyst-free synthesis of benzo[: D] imidazo[2,1- b] thiazoles and novel N -alkylated 2-aminobenzo [d] oxazoles under microwave irradiation

A highly efficient unprecedented catalyst-free microwave-assisted procedure for synthesizing benzo[d]imidazo[2,1-b]thiazoles and N-alkylated 2-aminobenzo[d]oxazol in green media was developed. The transformation provided rapid access to functionalized ben

Design and synthesis of 1,2,3-triazolo linked benzo[d]imidazo[2,1-b]thiazole conjugates as tubulin polymerization inhibitors

1,2,3-Triazolo linked benzo[d]imidazo[2,1-b]thiazole conjugates (5a–v) were designed, synthesized and evaluated for their cytotoxic potency against some human cancer cell lines like DU-145 (prostate), HeLa (cervical), MCF-7 (breast) HepG2 (liver) and A549 (lung). Preliminary results revealed that some of these conjugates like 5f and 5k exhibited significant antiproliferative effect against human breast cancer cells (MCF-7) with IC50 values of 0.60 and 0.78?μM respectively. Flow cytometric analysis of the cell cycle demonstrated an increase in the percentage of cells in the G2/M phase which was further authenticated by elevation of cyclin B1 protein levels. Immunocytochemistry revealed loss of intact microtubule structure in cells treated with 5f and 5k, and western blot analysis revealed that these conjugates accumulated more tubulin in the soluble fraction. Moreover, the conjugates caused apoptosis of the cells that was confirmed by mitochondrial membrane potential and Annexin V-FITC assay. Molecular docking studies indicated that these conjugates occupy the colchicine binding site of the tubulin protein.

Imidazole [2, 1-b] thiazole derivative as well as preparation method and application thereof

The invention belongs to the field of chemical pharmaceuticals, and particularly relates to an imidazole [2, 1-b] thiazole derivative as well as a preparation method and an application thereof. The structure of the imidazole [2, 1-b] thiazole derivative i

Discovery of imidazo[2,1- b ]thiazole HCV NS4B inhibitors exhibiting synergistic effect with other direct-acting antiviral agents

The design, synthesis, and SAR studies of novel inhibitors of HCV NS4B based on the imidazo[2,1-b]thiazole scaffold were described. Optimization of potency with respect to genotype 1b resulted in the discovery of two potent leads 26f (EC50 = 16

Arylcarboxyamino-substituted diaryl ureas as potent and selective FLT3 inhibitors

A series of diaryl ureas with an amide substitution at the 4-position was prepared and found to be potent and selective FLT3 inhibitors with good oral bioavailability and efficacy in a tumor xenograft model.

Discovery of novel Tricyclic full agonists for the G-protein-coupled niacin receptor 109A with minimized flushing in rats

Tricyclic analogues were rationally designed as the high affinity niacin receptor G-protein-coupled receptor 109A (GPR109A) agonists by overlapping three lead structures. Various tricyclic anthranilide and cycloalkene carboxylic acid full agonists were di

Tricyclic 6-alkylidene-penems as class-D beta-lactamases inhibitors

This invention relates to certain tricyclic 6-alkylidene penems which act as a inhibitor of class-D enzymes. β-Lactamases hydrolyze β-lactam antibiotics, and as such serve as the primary cause of bacterial resistance. The compounds of the present inventio

Structure-activity relationship of 6-methylidene penems bearing tricyclic heterocycles as broad-spectrum β-lactamase inhibitors: Crystallographic structures show unexpected binding of 1,4-thiazepine intermediates

The design and synthesis of a series of seven tricyclic 6-methylidene penems as novel class A and C serine β-lactamase inhibitors is described. These compounds proved to be very potent inhibitors of the TEM-1 and AmpC β-lactamases and less so against the class B metallo-β-lactamase CcrA. In combination with piperacillin, their in vitro activities enhanced susceptibility of all class C resistant strains from various bacteria. Crystallographic structures of a serine-bound reaction intermediate of 17 with the class A SHV-1 and class C GC1 enzymes have been established to resolutions of 2.0 and 1.4 A?, respectively, and refined to R-factors equal 0.163 and 0.145. In both β-lactamases, a seven-membered 1,4-thiazepine ring has formed. The stereogenic C7 atom in the ring has the R configuration in the SHV-1 intermediate and has both R and S configurations in the GC1 intermediate. Hydrophobic stacking interactions between the tricyclic C7 substituent and a tyrosine side chain, rather than electrostatic or hydrogen bonding by the C3 carboxylic acid group, dominate in both complexes. The formation of the 1,4- thiazepine ring structures is proposed based on a 7-endo-trig cyclization.