188672-83-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Benzothiazolecarbonitrile,6-nitro-(9CI) is utilized as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with diverse therapeutic properties. Its unique structure allows for the creation of molecules with potential medicinal applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Benzothiazolecarbonitrile,6-nitro-(9CI) serves as a crucial component in the production of various agrochemicals, including pesticides and herbicides, due to its reactive chemical nature which can be tailored for specific agricultural needs.
Used in Materials Science:
2-Benzothiazolecarbonitrile,6-nitro-(9CI) is applied in materials science for its potential to enhance or create new materials with improved properties, such as thermal stability or chemical resistance, contributing to the advancement of material technologies.
Used as a Precursor in Dyes and Pigments Synthesis:
2-Benzothiazolecarbonitrile,6-nitro-(9CI) is also used as a precursor in the synthesis of dyes and pigments, where its chemical structure plays a significant role in determining the color and stability of the final product, thus finding applications in various industries such as textiles, paints, and inks.

Upstream product

• 1048367-35-6 (Z)-2-bromo-N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4-nitroaniline 
• 13296-94-1 2-bromo-4-nitroaniline 
• 100-01-6 4-nitro-aniline 
• 2942-06-5 6-nitrobenzo[d]thiazole 
• 32137-76-1 benzothiazole-2-carboxylic acid ethyl ester 
• 2602-85-9 benzothiazole-2-carbonitrile 
• 29198-43-4 benzothiazole-2-amide 
• 4953-70-2 N-(p-Nitrophenyl)cyanothioformamide 
• 23451-98-1 2-amino-5-nitrobenzenethiol 
• 75318-43-3 4,5-dichloro-1,2,3-dithiazolium chloride 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 773837-37-9 sodium cyanide 
• 64-17-5 ethanol 
• 2407-11-6 2-chloro-6-nitrobenzothiazole 

Downstream Products

• 7724-12-1 2-cyano-6-aminobenzothiazole 

Relevant academic research and scientific papers

A "caged" Luciferin for Imaging Cell-Cell Contacts

Cell-cell interactions underlie fundamental biological processes but remain difficult to visualize over long times and large distances in tissues and live organisms. Bioluminescence imaging with luciferase-luciferin pairs is sufficiently sensitive to imag

Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole

2-Cyanobenzothiazoles (CBTs) are useful building blocks for: 1) luciferin derivatives for bioluminescent imaging; and 2) handles for bioorthogonal ligations. A particularly versatile CBT is 6-amino-2-cyanobenzothiazole (ACBT), which has an amine handle for straight-forward derivatisation. Here we present an economical and scalable synthesis of ACBT based on a cyanation catalysed by 1,4-diazabicyclo[2.2.2]octane (DABCO), and discuss its advantages for scale-up over previously reported routes.

Characterization of the reactivity of luciferin boronate - A probe for inflammatory oxidants with improved stability

Boronate derivatives of luciferin, containing oxidant-activated self-immolative moieties, recently have been developed for bioluminescent detection of hydrogen peroxide in animal models. Here, we report the synthesis and characterization of luciferin boronic acid pinacol ester (LBE) as a probe for detection of hydrogen peroxide, hypochlorous acid, and peroxynitrite, with improved stability and response time. HPLC analyses showed that LBE quickly hydrolyzes in phosphate buffer to luciferin boronic acid (LBA). Hydrogen peroxide oxidizes LBA slowly, with the formation of luciferase substrate, luciferin (Luc-OH), as the only product. Hypochlorite also oxidizes LBA to luciferin, but the subsequent reaction of Luc-OH with hypochlorite gives a chlorinated luciferin Luc–OH–Cl, which has a higher fluorescence quantum yield than luciferin at pH 7.4 and is also a substrate for luciferase (Takakura H, et. all. ChemBioChem 2012; 13:1424). Similar to other boronate probes, LBA is oxidized by peroxynitrite in two pathways. Luc-OH is the product of the major pathway, common for all the oxidants tested, whereas the non-fluorescent nitrated derivative, Luc-NO2, is formed in the minor pathway, specific for peroxynitrite. Formation of luciferin radical intermediate in the minor pathway has been confirmed by EPR spin trapping and mass spectrometric analyses of the spin adducts. We conclude that LBE shows potential as an improved probe for the detection of inflammatory oxidants in biological settings. Complementation of the bioluminescence measurements by HPLC or LC-MS-based identification of chlorinated and nitrated luciferin(s) will help identify the oxidants detected.

Synthesis and evaluation of D-thioluciferin, a bioluminescent 6'-thio analog of Dluciferin

All known light-emitting firefly-bioluminescent luciferin analogs are either derived from the 6'-hydroxy- and/or 6'-aminoluciferin. We report the synthesis of D-thioluciferin, a 6'-thio analog or isostere of D-luciferin, starting from p-aminothiophenol, using a unique thioacrylate-S-protecting-group strategy. Upon treatment of Dthioluciferin with purified Photinus pyralis (Ppy) luciferase (Luc), a bioluminescence emission with a red-shift λmax relative to D-luciferin was observed. It was also shown that disulphide and sulphide analogs of Dthioluciferin did not produce similar bioluminescences relative to D-thioluciferin when treated with Ppy Luc under standard conditions, thus, providing a foundation for the development of D-thioluciferin based probes based on disulphide reduction and S-dealkylation.

NOVEL CHEMILUMINESCENT SUBSTRATES FOR FACTOR XA

The present invention relates to chemiluminescent substrates of formulas (I-3) and (I-4) for blood clotting enzyme Factor Xa. The substrates are particularly useful for assaying coagulation factors and for quantifying an anticoagulant in a sample.

DERIVATIVES OF LUCIFERIN AND METHODS FOR THEIR SYNTHESIS

6-Thio derivatives of D-luciferin, also referred to as D-thioluciferins, having the general structure of Formula (I) are provided. Methods for synthesising D-luciferin, its derivatives, and their related 2-cyanobenzothiazole precursors are also provided. These compounds are commercially valuable due to their application in optical imaging, particularly in bioluminescence imaging.

Rapid and scalable assembly of firefly luciferase substrates

Bioluminescence imaging with luciferase-luciferin pairs is a popular method for visualizing biological processes in vivo. Unfortunately, most luciferins are difficult to access and remain prohibitively expensive for some imaging applications. Here we report cost-effective and efficient syntheses of d-luciferin and 6′-aminoluciferin, two widely used bioluminescent substrates. Our approach employs inexpensive anilines and Appel's salt to generate the luciferin cores in a single pot. Additionally, the syntheses are scalable and can provide multi-gram quantities of both substrates. The streamlined production and improved accessibility of luciferin reagents will bolster in vivo imaging efforts. This journal is

METHODS AND SYSTEMS FOR SYNTHESIS OF A D-AMINOLUCIFERIN PRECURSOR AND RELATED COMPOUNDS

Methods and systems to generate 6-amino-6-deoxy-D-luciferin precursor, 2-cyano-6-aminobenzothiazole and related compounds and derivatives

METHODS AND SYSTEMS FOR SYNTHESIS OF A D-AMINOLUCIFERIN PRECURSOR AND RELATED COMPOUNDS

Methods and systems to generate 6-amino-6-deoxy-D-luciferin precursor, 2-cyano-6-aminobenzothiazole and related compounds and derivatives

HETEROCYCLYLAMIDES AS GUT MICROSOMAL TRIGLYCERIDE TRANSPORT PROTEIN INHIBITORS

Compounds represented by formula (I) are inhibitors of gut microsomal triglyceride transfer protein. Such compounds are useful in treating diseases or conditions such as diabetes and obesity, along with patients are risk for developing such diseases or conditions.