4299-09-6

Usage

Uses

Used in Polymer Industry:
2-(2-hydroxyethyl)-1,2-benzothiazol-3(2H)-one is used as a photoinitiator for initiating polymerization reactions when exposed to ultraviolet light, leading to the crosslinking of polymer chains. This application is particularly relevant in UV-curable coatings, inks, and adhesives.
Used in UV-curable Coatings:
2-(2-hydroxyethyl)-1,2-benzothiazol-3(2H)-one is used as a catalyst to initiate the curing process of UV-curable coatings, providing a fast and efficient method for coating application and solidification.
Used in UV-curable Inks:
2-(2-hydroxyethyl)-1,2-benzothiazol-3(2H)-one is used as a photoinitiator in the formulation of UV-curable inks, enabling rapid curing upon exposure to ultraviolet light and ensuring quick drying and high-quality print results.
Used in UV-curable Adhesives:
2-(2-hydroxyethyl)-1,2-benzothiazol-3(2H)-one is used as a photoinitiator in the production of UV-curable adhesives, allowing for quick bonding and strong adhesion in various applications.

Upstream product

• 19602-82-5 2,2'-dithiodibenzoic acid dichloride 
• 141-43-5 ethanolamine 
• 3950-02-5 2-chlorosulfenylbenzoyl chloride 
• 54856-20-1 N-[2-(methoxycarbonyl)benzenesulfenyl]-1,2-benzisothiazolin-3-one 
• 7765-80-2 2,2'-dithiobis 
• 119-80-2 2,2'-dithiobenzoic acid 
• 1236311-86-6 2-ethylbenzo[d]-1,3-oxathiin-4-one 1-oxide 
• 38057-98-6 2-ethylbenzo[d]-1,3-oxathiin-4-one 
• 121995-13-9 N-(2-hydroxyethyl)-2-iodobenzamide 
• 147-93-3 Thiosalicylic acid 
• 55255-09-9 methyl 2-{[(2-hydroxyethyl)amino]thio}benzoate 
• 4892-02-8 Methyl thiosalicylate 
• 609-67-6 2-Iodobenzoyl chloride 
• 82891-94-9 N-(β-hydroxyethyl)-o-bromobenzamide 

Downstream Products

• 67388-03-8 2-[2-(N-methyl-anilino)-ethyl]-benzo[d]isothiazol-3-one 
• 49549-96-4 2-[2-(toluene-4-sulfonyloxy)-ethyl]-benzo[d]isothiazol-3-one 

Relevant academic research and scientific papers

Antimicrobial activity of N-hydroxyalkyl 1,2-benzisothiazol-3(2H)-ones and their thiono analogues

N-Hydroxyalkyl derivatives of 1,2-benzisothiazol-3(2H)-one and 1,2-benzisothiazol-3(2H)-thione have been prepared and their antifungal and antibacterial activity evaluated. Several compounds were active against selected fungi and Gram-positive microorganisms. Interesting activity was observed against the anaerobic strain Clostridium perfringens. Generally the more active compounds belong to the class of 1,2-benzisothiazol-3(2H)-ones. The retardation matches R(M) of the compounds was also evaluated but the results obtained show that lipophilicity has only a minor effect on the antimicrobial activity.

Facile synthesis and in vitro activity of n-substituted 1,2-benzisothiazol-3(2H)-ones against dengue virus NS2BNS3 protease

Several new N-substituted 1,2-benzisothiazol-3(2H)-ones (BITs) were synthesised through a facile synthetic route for testing their anti-dengue protease inhibition. Contrary to the conventional multistep synthesis, we achieved structurally diverse BITs with excellent yields using a two-step, one-pot reaction strategy. All the synthesised compounds were prescreened for drug-like properties using the online Swiss Absorption, Distribution, Metabolism and Elimination (SwissADME) model, indicating their favourable pharmaceutical properties. Thus, the synthesised BITs were tested for inhibitory activity against the recombinant dengue virus serotype-2 (DENV-2) NS2BNS3 protease. Dose–response experiments and computational docking analyses revealed that several BITs bind to the protease in the vicinity of the catalytic triad with IC50 values in the micromolar range. The DENV2 infection assay showed that two BITs, 2-(2-chlorophenyl)benzo[d]isothiazol-3(2H)-one and 2-(2,6-dichlorophenyl)benzo[d]isothiazol-3(2H)-one, could suppress DENV replication and virus infectivity. These results indicate the potential of BITs for developing new anti-dengue therapeutics.

Bioisosteric investigation of ebselen: Synthesis and in vitro characterization of 1,2-benzisothiazol-3(2H)-one derivatives as potent New Delhi metallo-β-lactamase inhibitors

Carbapenem-resistant Enterobacteriaceae (CRE) producing New Delhi metallo-β-lactamase (NDM-1) cause untreatable bacterial infections, posing a significant threat to human health. In the present study, by employing the concept of bioisosteric replacement of the selenium moiety of ebselen, we have designed, synthesized and characterized a small compound library of 2-substituted 1,2-benzisothiazol-3(2H)-one derivatives and related compounds for evaluating their cytotoxicity and synergistic activity in combination with meropenem against the E. coli Tg1 (NDM-1) strain. The most promising compound 3a demonstrated potent synergistic activity against a panel of clinically isolated NDM-1 positive CRE strains with FICI as low as 0.09. Moreover, its IC50 value and inhibition mechanism were also confirmed by using the enzyme inhibition assay and the ESI-MS analysis respectively. Importantly, compound 3a has acceptable toxicity and is not a PAINS. Because of its structural simplicity and potent synergistic activity in combination with meropenem, we propose that compound 3a may be a promising meropenem adjuvant and a new series of such compounds may worth further investigations.

1,2-BENZISOSELENAZOL-3(2H)-ONE AND 1,2-BENZISOTHIAZOL-3(2H)-ONE DERIVATIVES AS BETA-LACTAM ANTIBIOTIC ADJUVANTS

Provided herein are compositions and methods useful in the treatment of beta-lactam antibiotic resistant bacteria.

Ebsulfur as a potent scaffold for inhibition and labelling of New Delhi metallo-β-lactamase-1 in vitro and in vivo

The superbug infection caused by New Delhi metallo-β-lactamase (NDM-1) has grown into an emerging threat, labelling and inhibition of NDM-1 has proven challenging due to its shuttling between pathogenic bacteria. Here, we report a potent covalent scaffold, ebsulfur, for targeting the protein in vitro and in vivo. Enzymatic kinetic study indicated that eighteen ebsulfurs gained except 1a–b and 1f inhibited NDM-1, exhibiting an IC50 value ranging of 0.16–9 μM, and 1g was found to be the best, dose- and time-dependent inhibitor with an IC50 of 0.16 μM. Also, these ebsulfurs effectively restored the antibacterial activity of cefazolin against E. coli expressing NDM-1, and the best effect was observed to be from 1g, 1i and 1n, resulting in an 256-fold reduction in MIC of the antibiotic at a dose of 16 μg/mL. The equilibrium dialysis study implied that the ebsulfur disrupted the coordination of one Zn(II) ion at active site of NDM-1. Labelling of NDM-1 using a constructed fluorescent ebsulfur Ebs-R suggested that the inhibitor covalently bound to the target through SDS-PAGE analysis in vitro. Also, labelling NDM-1 in living E. coli cells with Ebs-R by confocal microscopic imaging showed the real-time distribution change process of intracellular recombinant protein NDM-1. Moreover, the cytotoxicity of these ebsulfurs against L929 mouse fibroblastic cells was tested, and their capability to restore antibacterial activity of antibiotic against clinical strains E. coli EC08 producing NDM-1 was determined. The ebsulfur scaffold proposed here is valuable for development of the covalent irreversible inhibitors of NDM-1, and also for labelling the target in vitro and in vivo.

Synthesis and anti-bacterial activity of a library of 1,2-benzisothiazol-3(2H)-one (BIT) derivatives amenable of crosslinking to polysaccharides

1,2-Benzisothiazol-3(2H)-one (BIT) is one of the most common chemical biocides in industrial products, with a heterocyclic structure and a wide range of antimicrobial activity. A library of BIT derivatives was synthesized and characterized, from which 18 compounds were selected, tested for anti-bacterial activity relative to the parent molecule and amenable of coupling to plant polysaccharides in general and to galactomannans (GM) in particular, widely used as rheology modifiers, but with limited “biostability”. Four sites on the BIT core were targeted: the nitrogen and the oxygen atoms on the heterocyclic ring, the C5 and the C6 positions on the aromatic ring, where functional groups were introduced. The ultimate aim of this work is to establish whether by covalently linking a biocide to GM polymers, their “biostability” can be improved.

Synthesis of 1,2-benzisothiazolin-3-ones by ring transformation of 1,3-benzoxathiin-4-one 1-oxides

1,2-Benzisothiazolin-3-ones were synthesized from 1,3-benzoxathiin-4-one 1-oxides by means of a nonhazardous and inexpensive method. The 1,3-benzoxathiin-4-one 1-oxides were prepared by oxidation of 1,3-benzoxathiin-4-ones with hydrogen peroxide in the presence of a catalyst. Attack of amines on the carbonyl groups of the 1,3-benzoxathiin-4-one 1-oxides and subsequent elimination of carbonyl compounds likely produced sulfenic acids, which then underwent ring closure to afford the 1,2-benzisothiazolin-3-ones.

An efficient copper mediated synthetic methodology for benzo[d]isothiazol- 3(2H)-ones and related sulfur-nitrogen heterocycles

A copper mediated sulfur-nitrogen coupling reaction for the synthesis of benzo[d]isothiazol-3(2H)-ones and related sulfur-nitrogen heterocycles has been presented, which requires 2-halo-arylamides, sulfur powder, 25-50 mol % of copper iodide/1,10-phenanthroline, and potassium carbonate as base.

An effective synthesis of N-substituted 2-sulfenamoylbenzoates and 1,2-benzisothiazolin-3-ones that uses 1,2-benzisothiazolin-3-one as a leaving group

N-Substituted 2-sulfenamoylbenzoates and 1,2-benzisothiazolin-3-ones were effectively synthesized by the substitution reaction between S-[2-(3-oxo-1,2-benzisothiazolinyl)]-2-mercaptobenzoates (2) and primary amines. The substitution reaction occurred on the sulfur atom of the 2-sulfenamoyl group of 2, and 1,2-benzisothiazolin-3-one behaved as a leaving group. The eliminated 1,2-benzisothiazolin-3-one could be reused as a starting material for the synthesis of 2. N,N-Disubstituted 2-sulfenamoylbenzoates were prepared by the reaction of 2 with secondary amines.