2406-90-8

Basic information

• Product Name: 2-Chlorobenzothiazo-6-amine
• Synonyms: 2-CHLORO-BENZOTHIAZOL-6-YLAMINE;6-Benzothiazolamine,2-chloro-(9CI);6-Benzothiazolamine, 2-chloro-;2-CHLOROBENZOTHIAZO-6-AMINE;2-Chloro-6-aminobenzothiazole;6-Amino-2-chlorobenzothiazole;2-CHLOROBENZOTHIAZO-6YL-AMINE;Benzothiazole, 6-amino-2-chloro- (6CI,7CI,8CI)
• CAS NO: 2406-90-8
• Molecular Formula: C₇H₅ClN₂S
• Molecular Weight: 184.65
• Product Categories: BENZOTHIAZOLE
• Mol File: 2406-90-8.mol

Chemical Properties

• Melting Point: 155-157 °C
• Boiling Point: 337.292 °C at 760 mmHg
• Flash Point: 157.789 °C
• Appearance: /
• Density: 1.532
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.763
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.09±0.10(Predicted)
• CAS DataBase Reference: 2-Chlorobenzothiazo-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chlorobenzothiazo-6-amine(2406-90-8)
• EPA Substance Registry System: 2-Chlorobenzothiazo-6-amine(2406-90-8)

Safety Data

• Hazardous Substances Data: 2406-90-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chlorobenzothiazo-6-amine is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure contributes to the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Chlorobenzothiazo-6-amine serves as an intermediate in the production of pesticides and other agrochemicals, helping to enhance crop protection and yield.
Used in Dye Industry:
2-Chlorobenzothiazo-6-amine is utilized as an intermediate in the synthesis of dyes, contributing to the coloration and performance of various dye products.
Used in Rubber Additives:
2-Chlorobenzothiazo-6-amine is used as a component in the manufacturing of rubber additives, improving the properties and performance of rubber materials.
Used in Corrosion Inhibitors:
It also plays a role in the production of corrosion inhibitors, helping to protect materials from degradation and extending their service life.

InChI:InChI=1/C7H5ClN2S/c8-7-10-5-2-1-4(9)3-6(5)11-7/h1-3H,9H2

Upstream product

• 2407-11-6 2-chloro-6-nitrobenzothiazole 
• 75-15-0 carbon disulfide 
• 106-50-3 1,4-phenylenediamine 
• 58263-00-6 6-azido-2-chloro-benzothiazole 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 

Downstream Products

• 58599-93-2 (2-chloro-benzothiazol-6-yl)-(3-nitro-benzylidene)-amine 
• 77563-27-0 2-methoxybenzo[d]thiazol-6-amine 
• 53306-17-5 2-hydrazino-benzothiazol-6-ylamine 
• 7724-12-1 2-cyano-6-aminobenzothiazole 
• 138962-06-8 N-[(2-chloro-benzothiazol-6-yl)amino]benzoic acid 
• 862822-09-1 2,6-dichloro-N-(2-chloro-benzothiazol-6-yl)-benzamide 
• 7714-23-0 N-(2-cyanobenzo[d]thiazol-6-yl)acetamide 
• 118969-27-0 2-(6-aminobenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid 
• 892841-01-9 4'-fluoro-biphenyl-4-carboxylic acid (2-chloro-benzothiazol-6-yl)-amide 
• 1318692-88-4 6-[6-(benzyloxycarbonylamino)hexylamino]-2-cyanobenzothiazole 
• 934270-88-9 6-benzylamino-2-cyanobenzothiazole 
• 934270-89-0 6-phenethylamino-2-cyanobenzothiazole 
• 934270-90-3 6-(3-phenylpropylamino)-2-cyanobenzothiazole 
• 1318692-71-5 6-(4-phenylbutylamino)-2-cyanobenzothiazole 

Relevant articles and documents

Site-specific immobilization of biomolecules by a biocompatible reaction between terminal cysteine and 2-cyanobenzothiazole

We report herein a new site-specific microarray immobilization method based on a biocompatible reaction between terminal cysteine and 2-cyanobenzothiazole (CBT). This immobilization strategy has been successfully applied to anchor small molecules, peptides and proteins onto microarrays.

Synthesis of N-Peptide-6-Amino-d-Luciferin Conjugates with Optimized Fragment Condensation Strategy

Abstract: The synthesis of peptide-luciferin conjugates has a pivotal role in the development of bioluminescent detection systems that are based on the determination of protease enzyme activity. This work describes the optimized synthesis of an N-peptide-6-amino-d-luciferin conjugate (Fmoc-Gly-Pro-6-amino-d-luciferin) with a simple fragment condensation method in adequate yields. Fmoc-Gly-Pro-6-amino-d-luciferin was produced from a previously synthesized Fmoc-Gly-Pro-OH and also previously synthesized 6-amino-2-cyanobenzothiazole with an optimized method, to which conjugate cysteine was added in an also improved way. The resulting conjugate was successfully used in a bioluminescent system, in vitro, demonstrating the applicability of the method. Graphical Abstract: [Figure not available: see fulltext.].

Aminoluciferins as functional bioluminogenic substrates of firefly luciferase

Firefly luciferase is widely used as a reporter gene in assays to study gene expression, gene delivery, and so on because of its extremely high signal-to-noise ratio. The availability of a range of bioluminogenic substrates would greatly extend the applicability of the luciferin-luciferase system. Herein, we describe a design concept for functional bioluminogenic substrates based on the aminoluciferin (AL) scaffold, together with a convenient, high-yield method for synthesizing N-alkylated ALs. We confirmed the usefulness of ALs as bioluminogenic substrates by synthesizing three probes. The first was a conjugate of AL with glutamate, Glu-AL. When Glu-AL, the first membrane-impermeable bioluminogenic substrate of luciferases, was applied to cells transfected with luciferase, luminescence was not observed; that is, by using Glu-AL, we can distinguish between intracellular and extracellular events. The second was Cy5-AL, which consisted of Cy5, a near-infrared (NIR) cyanine fluorescent dye, and AL, and emitted NIR light. When Cy5-AL reacted with luciferase, luminescence derived from Cy5 was observed as a result of bioluminescence resonance energy transfer (BRET) from AL to Cy5. The NIR emission wavelength would allow a signal to be observed from deeper tissues in bioluminescence in vivo imaging. The third was biotin-DEVD-AL (DEVD=the amino acid sequence Asp-Glu-Val-Asp), which employed a caspase-3 substrate peptide as a switch to control the accessibility of the substrate to luciferase, and could detect the activity of caspase-3 in a time-dependent manner. This generalized design strategy should be applicable to other proteases. Our results indicate that the AL scaffold is appropriate for a range of functional luminophores and represents a useful alternative substrate to luciferin.

Robust light emission from cyclic alkylaminoluciferin substrates for firefly luciferase

Firefly luciferase utilizes the chemical energy of ATP and oxygen to convert its substrate, d-luciferin, into an excited-state oxyluciferin molecule. Relaxation of this molecule to the ground state is responsible for the yellow-green light emission. Synthetic cyclic alkylaminoluciferins that allow robust red-shifted light emission with the modified luciferase Ultra-Glo are described. Overall light emission is higher than that of acyclic alkylaminoluciferins, aminoluciferin, and the native substrate d-luciferin.

DNA-damaging activity and mutagenicity of 16 newly synthesized thiazolo[5,4-a]acridine derivatives with high photo-inducible cytotoxicity

The discovery of the potent anticancer properties of natural alkaloids in the pyrido-thiazolo-acridine series has suggested that thiazolo-acridine derivatives could be of great interest. In a continuous attempt to develop DNA-binding molecules and DNA photo-cleavers, 16 new thiazolo[5,4-a]acridines were synthesized and studied for their photo-inducible DNA-intercalative, cytotoxic and mutagenic activities, by use of the DNA methyl-green bioassay, the Alamar Blue viability assay and the Salmonella mutagenicity test using strains TA97a and TA98 with and without metabolic activation and photo-activation. Without photo-activation, one compound showed a DNA-intercalative activity in the DNA major groove while three compounds displayed intercalating properties after photo-activation. In the dark, four molecules possessed cytotoxic activities against a THP1 acute monocytic leukemia cell line while 15 derivatives displayed photo-inducible cytotoxic activity against this cell line. All compounds were mutagenic in strain TA97a with metabolic activation (+S9mix) and 15 molecules were mutagenic in strain TA98 without activation (-S9mix). Study of the quantitative structure-activity relationships (QSAR) from the Salmonella mutagenicity data revealed that several descriptors could describe cytotoxic and mutagenic activities after photo-activation. From the results of the mutagenicity test, four compounds with elevated mutagenic activities were selected for additional experiments. Their capacities to induce single-strand breaks (SSB) and chromosome-damaging effects were monitored by the comet and the micronucleus assays in normal human keratinocytes. Comparison of the minimal genotoxic concentrations showed that two compounds possessed higher capacities to induce SSB after photo-activation. In the micronucleus assay, three molecules were able to induce high numbers of micronuclei following photo-activation. Overall, the results of this study confirm that acridines are predominantly genotoxic via a DNA-intercalating mechanism in the dark, while DNA-adducts were probably induced following photo-activation.

Novel luciferin derivatives

A compound represented by the following general formula (I) or a salt thereof: [wherein R1 and R2 represent hydrogen atom, a C1-6 alkyl group, or a group represented by the following formula (A): [wherein X1 and X2 represent hydrogen atom, or a group represented as —N(R3)(R4) (R3 and R4 represent hydrogen atom, a C1-6 alkyl group, a C1-6 alkylcarbonyl group, or a C1-6 alkyloxycarbonyl group); and n represents an integer of 1 to 6], provided that R1 and R2 do not simultaneously represent hydrogen atom), which is a novel luciferin derivative that serves as a luciferase substrate.

NOVEL MCH RECEPTOR ANTAGONISTS

The present invention relates to a melanin concentrating hormone antagonist compound of formula (I); wherein Ar1, L1, R1, q, X, R2, R3, R4, and R5 are as defined, or a pharmaceutically acceptable salt, solvate, or enantiomer thereof useful in the treatment, prevention or amelioration of symptoms associated with obesity and related diseases.

Synthesis and biological evaluation of benzothiazole derivatives as potent antitumor agents

Based on 2-methyl-4-nitro-2H-pyrazole-3-carboxylic acid[2- (cyclohexanecarbonylamino)benzothiazol-6-yl]amide (1), which shows selective cytotoxicity against tumorigenic cell lines, 2,6-dichloro-N-[2- (cyclopropanecarbonylamino)benzothiazol-6-yl]benzamide (13b) was designed and synthesized as a biologically stable derivative containing no nitro group. The highly potent derivative 13b exhibited excellent in vivo inhibitory effect on tumor growth.

INHIBITORS OF 11-BETA-HYDROXY STEROID DEHYDROGENASE TYPE 1 AND TYPE 2

There is provided a compound having Formula (I): wherein one of R1 and R2 is a group of the Formula (a), wherein R4 is selected from H and hydrocarbyl, R5 is a hydrocarbyl group and L is an optional linker group, or R1 and R2 together form a ring substituted with the group (Formula (a)) wherein R3 is H or a substituent, and wherein X is selected from S, O, NR6 and C(R7)(R8), wherein R6 is selected from H and hydrocarbyl groups, wherein each of R7 and R8 are independently selected from H and hydrocarbyl groups.

In vitro activities of position 2 substitution-bearing 6-nitro- and 6-amino-benzothiazoles and their corresponding anthranilic acid derivatives against Leishmania infantum and Trichomonas vaginalis.

6-Nitro- and 6-amino-benzothiazoles bearing different chains in position 2 and their corresponding anthranilic acid derivatives were investigated for their in vitro antiparasitic properties against parasites of the species Leishmania infantum and Trichomonas vaginalis compared to their toxicity towards human monocytes. Biological investigations established that the antiprotozoal properties depended greatly on the chemical structure of the position 2 substitution-bearing group. Compound C1, 2-[(2-chloro-benzothiazol-6-yl) amino] benzoic acid, demonstrated an interesting antiproliferative activity towards parasites of the species T. vaginalis, while compound C11, 2-([2-[(2-hydroxyethyl) amino]-benzothiazol-6-yl] amino) benzoic acid, exhibited a promising activity against parasites of the species L. infantum in their intracellular amastigote form. Additional experiments established that compound C11, which was poorly toxic against the promastigote and the extracellular amastigote forms of the parasite, could improve host-protective mechanisms against Leishmania by preventing parasite internalization by macrophages and stimulating NO production, by means of a mechanism synergistically enhanced by the presence of gamma interferon.