114095-04-4

Basic information

• Product Name: IMIDAZO[2,1-B]BENZOTHIAZOLE-2-CARBOXALDEHYDE
• Synonyms: IMIDAZO[2,1-B]BENZOTHIAZOLE-2-CARBOXALDEHYDE;Benzo[d]iMidazo[2,1-b]thiazole-2-carbaldehyde
• CAS NO: 114095-04-4
• Molecular Formula: C₁₀H₆N₂OS
• Molecular Weight: 202.23
• Mol File: 114095-04-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 208-209 °C
• Appearance: /
• Density: 1.49±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.14±0.40(Predicted)
• CAS DataBase Reference: IMIDAZO[2,1-B]BENZOTHIAZOLE-2-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: IMIDAZO[2,1-B]BENZOTHIAZOLE-2-CARBOXALDEHYDE(114095-04-4)
• EPA Substance Registry System: IMIDAZO[2,1-B]BENZOTHIAZOLE-2-CARBOXALDEHYDE(114095-04-4)

Safety Data

• Hazardous Substances Data: 114095-04-4(Hazardous Substances Data)

Usage

Description

Imidazo[2,1-b]benzothiazole-2-carboxaldehyde is a versatile chemical compound belonging to the imidazole family, characterized by the presence of a benzothiazole ring. It is renowned for its diverse biological and chemical properties, which include antimicrobial, antifungal, and anticancer activities. This makes it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and dyes, and has garnered significant interest in medicinal chemistry and chemical biology for its potential applications.

Uses

Used in Pharmaceutical Industry:
Imidazo[2,1-b]benzothiazole-2-carboxaldehyde is used as a key intermediate in the synthesis of various therapeutic agents due to its biological activities. Its antimicrobial, antifungal, and anticancer properties make it a promising candidate for the development of new drugs to combat infections and cancer.
Used in Agrochemical Industry:
In the agrochemical sector, Imidazo[2,1-b]benzothiazole-2-carboxaldehyde is utilized as a component in the creation of pesticides and other agrochemicals, leveraging its antimicrobial and antifungal properties to protect crops and enhance agricultural productivity.
Used in Dye Industry:
Imidazo[2,1-b]benzothiazole-2-carboxaldehyde is also employed in the synthesis of dyes, where its chemical properties contribute to the development of novel colorants for various applications, including textiles and other industrial uses.
Used as a Fluorescent Probe:
Imidazo[2,1-b]benzothiazole-2-carboxaldehyde is used as a fluorescent probe for detecting metal ions, capitalizing on its ability to interact with these ions and provide a visual or measurable response, which is crucial in chemical analysis and environmental monitoring.
Used as an Enzyme Inhibitor:
Furthermore, it serves as an enzyme inhibitor, where its interaction with specific enzymes can modulate biological processes, offering potential therapeutic benefits in the treatment of various diseases by controlling enzyme activity.
Overall, Imidazo[2,1-b]benzothiazole-2-carboxaldehyde's multifaceted applications across different industries underscore its importance and potential in chemical and biological research and development.

Upstream product

• 21224-16-8 2-amino-6-ethylbenzo[d]thiazole 
• 136-95-8 2-amino-benzthiazole 
• 64951-05-9 ethyl imidazo[2,1-b]-benzthiazole-2-carboxylate 
• 114095-02-2 imidazo[2,1-b]benzothiazole-2-methanol 

Downstream Products

• 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 
• 114094-91-6 Benzo[d]imidazo[2,1-b]thiazol-2-yl-phenyl-methanone 

Relevant articles and documents

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

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.

HETEROTRICYCLYL 6-ALKYLIDENE-PENEMS AS ΒΕΤΑ-LACTAMASE INHIBITORS

The present invention provides a compound of formula I, pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof.