23474-98-8

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-5-CHLOROTHIOPHENOL is used as a reagent for the preparation of indane-based 1,5-benzothiazapines, which possess antimicrobial activity. These benzothiazapines are valuable in the development of new drugs to combat various microbial infections, including bacterial and fungal pathogens.

Upstream product

• 106-47-8 4-chloro-aniline 
• 35576-53-5 6-Chloro-1,2,3-benzodithiazol-1-ium chloride 
• 31183-89-8 2-[(2-amino-5-chlorophenyl)dithio]-4-chlorophenylamine 
• 59280-70-5 4'-chloro-2'-fluoroacetanilide 
• 95-24-9 6-chloro-2-aminobenzothiazole 
• 1367199-79-8 BrH*C₇H₅ClN₂S 
• 3696-23-9 N-(4-chlorophenyl)thiourea 
• 57946-56-2 2-fluoro-4-chloroaniline 
• 4146-24-1 6-chloro-2-methylbenzo[d]thiazole 
• 2942-10-1 6-chloro-1,3-benzothiazole 

Downstream Products

• 418783-16-1 (2-amino-5-chloro-phenylsulfanyl)-acetic acid 
• 108650-65-3 2-tert-butyl-6-chloro-2-methyl-2,3-dihydro-benzothiazole 
• 54531-34-9 1-(6-chloro-1H-benzothiazol-2-yl)ethanol 
• 60598-36-9 6-anilino-9-chloro-benzo[a]phenothiazin-5-one 
• 106629-28-1 {2-[4-(6-chloro-benzothiazol-2-yl)-phenoxy]-ethyl}-triethyl-ammonium; iodide 
• 31183-89-8 2-[(2-amino-5-chlorophenyl)dithio]-4-chlorophenylamine 
• 19843-51-7 3-chloro-12H-quinoxalino<2,3-b><1,4>benzothiazine 
• 31639-76-6 3-chloro-8-methyl-12H-benzo[5,6][1,4]thiazino[2,3-b]quinoxaline 
• 14468-66-7 6-chloro-2-trichloromethyl-benzothiazole 
• 64377-93-1 ethyl 6-chlorobenzothiazole-2-carboxylate 
• 31639-73-3 3-chloro-8,9-dinitro-12H-benzo[5,6][1,4]thiazino[2,3-b]quinoxaline 
• 99839-04-0 6-chloro-2,2-dimethyl-2,3-dihydro-benzothiazole 
• 20988-73-2 10-chloro-2,3-dimethoxy-7H-benzo[5,6][1,4]thiazino[3,2-c]cinnoline 
• 110766-90-0 8-Chloro-2-methyl-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 

Relevant academic research and scientific papers

Synthesis and insecticidal evaluation of novel sulfide-containing amide derivatives as potential ryanodine receptor modulators

With the aim of discovering new bioactive pesticides for crop protection, a series of novel sulfide-containing amide derivatives A were efficiently synthesized via a strategy of modifying the “amide” structure of anthranilic diamide insecticides. The single-crystal structures of A2-3 and A4-5 were firstly reported. The bioassay results showed that most of the synthesized compounds display moderate to high insecticidal activities. Particularly, some sulfone-containing compounds, e.g., A2-3, A3-3 and A6-3, not only possessed favorable lethality rate (50%–100%) against P. xylostella at a concentration of 0.1 mg/L, but also held good activities towards a variety of agricultural pests such as M. separata, C. pipiens pallen, H. armigera and O. nubilalis; the larvicidal activities of A4-1 and A6-1 towards P. xylostella were close to that of chlorantraniliprole at 0.01 mg/L. The calcium imaging experiments revealed that the representative compounds A2-3 and A6-3 are potential ryanodine receptor (RyR) modulators. The structure–activity relationships were discussed in detail. These results provide useful information for further design and development of novel insecticides.

Synthesis and evaluation of novel 2,4-diaminopyrimidines bearing a sulfoxide moiety as anaplastic lymphoma kinase (ALK) inhibition agents

Anaplastic lymphoma kinase (ALK) targeted therapies have demonstrated remarkable efficacy in ALK-positive lung adenocarcinomas. Here we synthesized and evaluated sixteen new 2,4-diaminopyrimidines bearing a sulfoxide moiety as anaplastic lymphoma kinase (ALK) inhibitors. The optimal compound 9e exhibited excellent antiproliferative activity against non-small cell lung cancer NCI-H2228 cells, which is better than that of Brigatinib and similar to Ceritinib. Mechanism study revealed that the optimal compound 9e decreased the mitochondrial membrane potential and arrested NCI-H2228 cells in the G0/G1 phase, finally resulting in cellular apoptosis. It is interesting that 9e could effectively inhibit the migration of NCI-H2228 cells and may be a promising leading compound for chemotherapy of metastatic cancer.

Facile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization

3-CF3S substituted thioflavones and benzothiophenes were achieved via the reactions of AgSCF3 with methylthiolated alkynones and alkynylthioanisoles, respectively, promoted by persulfate. This protocol possesses good functional group tolerance and high yields. Mechanistic studies suggested that a classic two-step radical process was involved, which includes addition of CF3S radical to triple bond and cyclization with SMe moiety.

Convenient and efficient synthesis of novel 11: H -benzo[5,6][1,4]thiazino[3,4- a] isoindol-11-ones derived from 2-bromo-(2/3-substitutedphenyl)-1 H -indene-1,3(2 H)-diones

An unprecedented formation of 11H-benzo[5,6][1,4]thiazino[3,4-a]isoindol-11-ones through a one-step reaction of differently substituted 2-aminobenzenethiols and 2-bromo-(2/3-substitutedphenyl)-1H-indene-1,3(2H)-diones in freshly dried ethanol under reflux conditions has been investigated. This unique transformation probably occurs through an initial nucleophilic substitution followed by ring opening and subsequent intramolecular cyclization. The structures of all the synthesized benzo[1,4]thiazino isoindolinones were established by FTIR, 1H NMR, 13C NMR, HRMS, and X-ray crystallographic analysis. This approach was found to be simple and convenient and provides several advantages such as substantial atom economy, short reaction time and operational simplicity.

ANTIBIOTIC COMPOUNDS

The present invention relates to antibiotic compounds of formula (I), to compositions containing these compounds and to methods of treating bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Gram-positive and/or Gram-negative bacteria, and in particular in the treatment of infection with, and diseases caused by, Neisseria gonorrhoeae.

Synthesis of Indane-Based 1,5-Benzothiazepines Derived from 3-Phenyl-2,3-dihydro-1H-inden-1-one and Antimicrobial Studies Thereof

In the present study, a series of 20 indane-based 1,5-benzothiazepines (5a–t) has been prepared derived from 3-phenyl-2,3-dihydro-1H-inden-1-one (1). All the synthesized 1,5-benzothiazepines (5a–t) were screened for their in vitro antimicrobial activities against four bacteria [Bacillus subtilis (MTCC 441), Staphylococcus epidermidis (MTCC 6880), Escherichia coli (MTCC 1652), and Pseudomonas aeruginosa (MTCC 424)] and two fungi [Candida albicans (MTCC 227) and Aspergillus niger (MTCC 8189)]. Among all the tested derivatives, 5n and 5o against E.?coli displayed more inhibitory activity than that of the reference drug, ciprofloxacin, while the derivatives 5c, 5m–o, 5s, and 5t against C.?albicans, and 5d, 5e, 5n, 5o, 5s, and 5t against A.?niger were found to be more potent than the standard drug, that is, fluconazole.

Synthesis of bioactive substituted pyrazolylbenzothiazinones

Abstract Pyrazolylbenzothiazinones have been synthesized in good yields by the reaction of 2-hydrazinocarbonymethyl-3,4-dihydro-2H-1,4-benzothiazin-3-ones with β-diketone in the presence of ethanol. The structures of synthesized pyrazolylbenzothiazinones were confirmed on the basis of their analytical and spectral data. The antimicrobial activities of the synthesized compounds have also been included.

Synthesis and antimicrobial activity of 2,4-diaryl-2,3-dihydrobenzo[b][1,4] thiazepines

A new series of structurally diverse 2,3-dihydrobenzo[b][1,4]thiazepines (2,3-dihydro-1,5-benzothiazepines) with substituted phenyl groups at C(2) and C(4) have been synthesized by reaction of 3-(5-bromo-2-methoxyphenyl)-1- arylpropen-1-ones with 2-aminobenzenethiols. The structures of all the synthesized compounds were confirmed by their analytical and spectral data (IR, 1H NMR, 13C NMR). All the synthesized compounds were evaluated for antibacterial and antifungal activity against a variety of bacterial and fungal strains and interesting results were obtained. Some of the compounds had antibacterial and antifungal activity comparable to that of ciprofloxacin and fluconazole.

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.

Synthesis and antimicrobial activity of structurally flexible heterocycles with the 1,4-thiazine heterosystem

In this work, 4H-1,4-benzothiazines were synthesized by an efficient synthetic method in a single step involving heterocyclization of substituted 2-aminobenzenethiols with β-ketoester. The structures of the synthesized compounds were confirmed by their analytical and spectral data. The synthesized compounds were evaluated for their antimicrobial activity against bacterial species; E. coli and Bacillus cereus. The synthesized compounds showed significant activity against microorganisms, which can be correlated with the privileged heterocyclic structural scaffolds.