23451-98-1

Usage

Uses

Used in Organic Synthesis:
2-Amino-5-nitrobenzenethiol is used as a reagent in organic synthesis for its ability to participate in a variety of chemical reactions, contributing to the formation of new compounds with potential applications in different industries.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, 2-Amino-5-nitrobenzenethiol is used as a precursor in the development of new drugs, leveraging its potential antioxidant properties and its capacity to be modified for specific therapeutic uses.
Used in Antimicrobial Agents:
2-Amino-5-nitrobenzenethiol is utilized as an antimicrobial agent for its ability to inhibit the growth of certain bacteria, making it a candidate for use in products aimed at controlling microbial populations in various settings.
Used in Chemical Research:
In the field of chemical research, 2-Amino-5-nitrobenzenethiol serves as a subject of study for understanding its properties and potential reactions, which can lead to the discovery of new chemical processes and applications.

Upstream product

• 2942-06-5 6-nitrobenzo[d]thiazole 
• 2941-63-1 2-methyl-6-nitrobenzothiazole 
• 95-16-9 1,3-Benzothiazole 
• 100-01-6 4-nitro-aniline 
• 2407-11-6 2-chloro-6-nitrobenzothiazole 
• 6285-57-0 2-amino-6-nitrobenzothiazole 
• 4308-10-5 2-methoxy-6-nitrobenzo[d]thiazole 

Downstream Products

• 53544-75-5 6-nitro-2-(3-nitrophenyl)benzothiazole 
• 53544-74-4 2-(4'-nitrophenyl)-6-nitrobenzothiazole 
• 1221688-93-2 6-nitro-2-(4-cyanophenyl)benzothiazole 
• 53544-77-7 2-(4-methoxy-phenyl)-benzothiazol-6-ylamine 
• 1426262-48-7 C₁₅H₁₁ClN₂OS 
• 1426262-49-8 C₁₅H₁₀ClFN₂OS 
• 1426262-50-1 C₁₆H₁₃ClN₂O₂S 
• 1426262-52-3 C₂₈H₃₂N₄O₂S₂ 
• 1426262-53-4 C₂₈H₃₁FN₄O₂S₂ 
• 1426262-54-5 C₂₉H₃₄N₄O₃S₂ 
• 1426262-55-6 C₂₈H₃₄N₄OS₂ 
• 1426262-56-7 C₂₈H₃₃FN₄OS₂ 
• 1426262-57-8 C₂₉H₃₆N₄O₂S₂ 
• 6392-97-8 2-phenylbenzo[d]thiazole-6-amine 

Relevant academic research and scientific papers

A Double-Clicking Bis-Azide Fluorogenic Dye for Bioorthogonal Self-Labeling Peptide Tags

Herein, we give the very first example for the development of a fluorogenic molecular probe that combines the two-point binding specificity of biarsenical-based dyes with the robustness of bioorthogonal click-chemistry. This proof-of-principle study reports on the synthesis and fluorogenic characterization of a new, double-quenched, bis-azide fluorogenic probe suitable for bioorthogonal two-point tagging of small peptide tags by double strain-promoted azide-alkyne cycloaddition. The presented probe exhibits remarkable increase in fluorescence intensity when reacted with bis-cyclooctynylated peptide sequences, which could also serve as possible self-labeling small peptide tag motifs. The first example of a fluorogenic molecular probe has been developed that combines the two-point binding specificity of biarsenical-based dyes with the robustness of bioorthogonal click-chemistry. The new, double-quenched, bis-azide fluorogenic probe can bind to small bis-cyclooctynylated peptide tags through a double strain-promoted click reaction (see figure; SPAAC=strain-promoted alkyne-azide cycloaddition). The probe exhibits remarkable increase in fluorescence intensity with peptide sequences that can serve as possible self-labeling small peptide tags.

Efficient synthesis of a new bifunctional Cu(I) chelator

Abstract Herein we report an efficient eight-step synthesis of N1-(3-(methylthio)propyl)-2-((3-(methylthio)propyl)thio)benzene-1,4-diamine (1) from 6-nitrobenzo[d]thiazole. Incorporation of a nitro rather than a hydroxyl functionality off the a

Design, synthesis and biological evaluation of new benzoxazolone/benzothiazolone derivatives as multi-target agents against Alzheimer's disease

In this study, four series of compounds with benzoxazolone and benzothiazolone cores were designed, synthesized and evaluated as multifunctional agents against Alzheimer's disease (AD). Additionally, in order to shed light on the effect of the carbonyl groups of benzoxazolone/benzothiazolone, benzoxazole/benzothiazole-containing analogues were also synthesized and evaluated. Inhibition potency of all final compounds towards cholinesterase enzymes and their antioxidant activity were tested. Subsequently, the anti-inflammatory activity, cytotoxicity, apoptosis, and Aβ aggregation inhibition tests were also performed for selected compounds. The results indicated that compounds 11c, a pentanamide derivative with benzothiazolone core, and 14b, a keton derivative with benzothiazolone core, were considered as promising multi-functional agents for further investigation against AD. The reversibility, kinetic and molecular docking studies were also performed for the compounds with the highest AChE 14b (eeAChE IC50 = 0.34 μM, huAChE IC50 = 0.46 μM) and BChE 11c (eqBChE IC50 = 2.98 μM, huBChE IC50 = 2.56 μM) inhibitory activities.

Green synthesis and biological evaluation of 6-substituted-2-(2-hydroxy/methoxy phenyl)benzothiazole derivatives as potential antioxidant, antibacterial and antitumor agents

We present a new efficient green synthetic protocol for introduction of substituents to the C-6 position of 2-arylbenzothiazole nuclei. Newly synthesized compounds were designed to study the influence of the hydroxy and methoxy groups on the 2-arylbenzothiazole scaffold, as well as the influence of the type of substituents placed on the C-6 position of benzothiazole moiety on biological activity, including antibacterial, antitumor and antioxidant activity. Modest activity was observed against the tested Gram-positive and Gram-negative bacterial strains for only amidino derivatives 5d and 6d. The tested compounds exhibited moderate to strong antiproliferative activity towards the tumor cell lines tested. The SAR study revealed that the introduction of substituents into the benzene ring of the benzothiazole nuclei is essential for antiproliferative activity, while introduction of the hydroxy group into the 2-aryl moiety of the 2-arybenzothiazole scaffold significantly improved selectivity against tumor cell lines. The observed results revealed several novel 6-substituted-2-arylbenzothiazole compounds, 5b, 5c, 5f and 6f, with strong and selective antiproliferative activity towards HeLa cells in micro and submicromolar concentrations, with the most selective compounds being 6-ammonium-2-(2-hydroxy/methoxyphenyl)benzothiazoles 5f and 6f. The compound 5f bearing the hydroxy group on the 2-arylbenzothiazole core showed the most promising antioxidative activity evaluated by DPPH, ABTS and FRAP in vitro assays. The presence of the amino protonated group attached at the benzothiazole moiety was essential for the antiproliferative and antioxidant activity observed, exerted through a change in the levels of the reactive oxygen species-modulated HIF-1 protein.

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

A COMPOUND AND PHARMACEUTICAL COMPOUND FOR TREATMENT OF INFLAMMATORY DISEASES

The present invention relates to a pharmaceutical composition for treating inflammatory diseases, comprising: a compound represented by chemical formula I, a pharmaceutically acceptable salt thereof; a hydrate thereof; or a compound as a solvate thereof,

SELECTIVE ANDROGEN RECEPTOR MODULATORS

This invention provides compounds of formula I, pharmaceutical compositions comprising a compound of formula I and a pharmaceutically acceptable excipient, methods of modulating the androgen receptor, methods of treating diseases beneficially treated by an androgen receptor modulator (e.g., sarcopenia, prostate cancer, contraception, type 2 diabetes related disorders or diseases, anemia, depression, and renal disease) and processes for making compounds and intermediates useful in the preparation of same.

Fluorescence properties of 5-(5,6-dimethoxybenzothiazol-2-yl)-2′- deoxyuridine (dbtU) and oligodeoxyribonucleotides containing d btU

We describe the synthesis and photophysical properties of 11 substituted 5-(benzothiazol-2-yl)-2′-deoxyuridine derivatives and oligodeoxyribonucleotides (ODNs) containing 5-(5,6-dimethoxybenzothiazol-2-yl)- 2′-deoxyuridine (dbtU), which was the strongest fluorescent derivative among those prepared. The fluorescence properties of dbtU itself and ODNs containing dbtU show the same tendency of being weaker in both neutral and acidic solution and stronger in basic solution. The ODNs (15mer) containing 16 combinations of 5′-XbtU-3′ and 5′-btUY-3′, where X, Y = A, T, G, or C, were synthesized, and their fluorescence intensity and quantum yield in basic solution were compared. On average, only the ODN with the 5′-G btU-3′ sequence shows a 7.9-fold lower fluorescence intensity than the other sequences. Ab initio calculations of 5′-G btU-3′ and 5′-btUG-3′ as models under basic conditions suggest that the lower fluorescence of the ODN containing the 5′-GbtU-3′ sequence is caused by a wider overlap between stacked guanine (Gua) and btUra than that of the 5′- btUG-3′ sequence and that the HOMO is delocalized not only on btUra but also on Gua.

BENZOXAZINES, BENZOTHIAZINES, AND RELATED COMPOUNDS HAVING NOS INHIBITORY ACTIVITY

The present invention features benzoxazines, benzothiazines, and related compounds that inhibit nitric oxide synthase (NOS), particularly those that selectively inhibit neuronal nitric oxide synthase (nNOS) in preference to other NOS isoforms. The NOS inh

Novel amidino substituted 2-phenylbenzothiazoles: Synthesis, antitumor evaluation in vitro and acute toxicity testing in vivo

The efficient synthesis of new bis-substituted nitro-amidino, amino-amidino (10a, 10b-13a, 13b) and previously prepared diamidino 2-phenyl-benzothiazoles (9a, 9b) is described. The compounds 11a and 11b were prepared by recently developed methodology of the key precursors in zwitterionic form 8a and 8b with 4-nitrobenzoylchloride in a very good yield (70%). All compounds except diamidino-substituted 2-phenylbenzothiazole 9a show exceptionally prominent tumor cell-growth inhibitory activity and cytotoxicity, whereby the special selectivity of amino-amidine 2-phenylbenzothiazole 12a towards MCF-7 and H 460 cells makes this compound a prospective lead compound that should be further evaluated in animal models. All in vivo tested compounds (12a, 12b, 13a and 13b) are absorbed from mice gastrointestinal system. LD50 are between 67.33 and 696.2 mg/kg body weight (OECD/EPA toxicity categories 2-3).