82152-06-5

Basic information

• Product Name: 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetic acid
• Synonyms: 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetic acid;2-(3-keto-1,2-benzothiazol-2-yl)acetic acid;2-(3-oxo-1,2-benzothiazol-2-yl)acetic acid;2-(3-oxo-1,2-benzothiazol-2-yl)ethanoic acid;2-(3-Oxo-3h-benzo[d]isothiazol-2-yl)-acetic acid
• CAS NO: 82152-06-5
• Molecular Formula: C₉H₇NO₃S
• Molecular Weight: 209.22178
• EINECS: -0
• Mol File: 82152-06-5.mol

Chemical Properties

• Melting Point: 240-242 °C(Solv: water (7732-18-5))
• Boiling Point: 444.9±47.0 °C(Predicted)
• Appearance: /
• Density: 1.518±0.06 g/cm3(Predicted)
• PKA: 3.61±0.10(Predicted)
• CAS DataBase Reference: 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetic acid(82152-06-5)
• EPA Substance Registry System: 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetic acid(82152-06-5)

Safety Data

• Hazardous Substances Data: 82152-06-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetic acid is used as a key intermediate in the synthesis of pharmaceuticals. Its potential biological activity and role in various biological processes make it a promising candidate for the development of new drugs and compounds.
Used in Agrochemical Synthesis:
In the agrochemical industry, 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetic acid is utilized as a building block in the synthesis of agrochemicals. Its unique structure and properties contribute to the development of effective and innovative products for agricultural applications.
Used in Organic Synthesis and Chemical Research:
2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetic acid is also employed as a building block in organic synthesis and chemical research. Its versatile structure allows for the creation of a wide range of compounds with various applications in different industries.

Upstream product

• 4299-16-5 (1,2-Benzisothiazolin-3-on-2-yl)essigsaeureethylester 
• 58249-25-5 sale sodico del 1,2-benzisotiazolin-3-one 
• 19602-82-5 2,2'-dithiodibenzoic acid dichloride 
• 22219-02-9 2,2'-thiodibenzoic acid 
• 2634-33-5 1,2-benzisothiazolin-3-one 
• 79-11-8 chloroacetic acid 
• 1344678-67-6 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetic acid tert-butyl ester 
• 119-80-2 2,2'-dithiobenzoic acid 
• 3950-02-5 2-chlorosulfenylbenzoyl chloride 
• 56-40-6 glycine 

Downstream Products

• 1207983-14-9 N-(4-(3-bromoanilino)quinazolin-6-yl)-2-(3-oxobenzo[d]isothiazolin-2-yl)acetamide 
• 1344678-65-4 (S)-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)-N-(1-phenylethyl)acetamide 
• 1344678-66-5 (R)-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)-N-(1-phenylethyl)acetamide 
• 1344678-63-2 N-benzyl-N-ethyl-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide 
• 902839-50-3 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)-N-phenethylacetamide 
• 876941-05-8 N-(4-methoxybenzyl)-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide 
• 1344678-60-9 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)-N-phenylacetamide 
• 1220637-44-4 N-benzyl-N-methyl-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide 
• 878082-31-6 methyl 2-(2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamido)benzoate 
• 902839-54-7 N-(4-fluorobenzyl)-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide 
• 1344678-62-1 N-methyl-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)-N-phenylacetamide 
• 876910-77-9 N-benzyl-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide 
• 1360180-33-1 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)-N-(3-(prop-2-ynyloxy)phenyl)acetamide 
• 1360180-35-3 N-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-2-(3-oxobenzo-[d]isothiazol-2(3H)-yl)acetamide 

Relevant articles and documents

Synthesis and antimicrobial activity of novel benzisothiazolin-3-one acetamide derivatives

A series of novel 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)-N-substituted phenylacetamide (4a-4e) have been synthesized from benzo [d]isothiazol-3(2H)-one (BIT) and substituted aniline. These benzisothiazolin-3-one acetamide derivatives (4a-4e) were identified by IR, 1H NMR and elemental analyses. Their antimicrobial activities were also evaluated.

Discovery of highly potent SARS-CoV-2 Mpro inhibitors based on benzoisothiazolone scaffold

The COVID-19 pandemic has drastically impacted global economies and public health. Although vaccine development has been successful, it was not sufficient against more infectious mutant strains including the Delta variant indicating a need for alternative treatment strategies such as small molecular compound development. In this work, a series of SARS-CoV-2 main protease (Mpro) inhibitors were designed and tested based on the active compound from high-throughput diverse compound library screens. The most efficacious compound (16b-3) displayed potent SARS-CoV-2 Mpro inhibition with an IC50 value of 116 nM and selectivity against SARS-CoV-2 Mpro when compared to PLpro and RdRp. This new class of compounds could be used as potential leads for further optimization in anti COVID-19 drug discovery.

Benzo[d]isothiazole-3-(2H)-one derivative, preparation method and application thereof

The invention relates to a benzo[d]isothiazole-3-(2H)-one derivative, a preparation method and application of the benzo[d]isothiazole-3-(2H)-one derivative. The compound is a free alkali or salt of acompound with a structure shown in a general formula (I). The salt is one of hydrochloride, hydrobromide, sulfate, trifluoroacetate, tartrate, lactate or mesylate; R1 independently represents "-CH2-CO-" or "-CH2-CH2-"; R2 independently represents "-CH2-CH2-O-" or "-CO-CH=CH-"; R3 independently represents hydrogen, halogens, a hydrocarbon group, a halogen-substituted hydrocarbon group, a nitro group, an amino group, a nitrile group, a hydroxyl group, an alkoxy group, an aryloxy group, a heterocycloalkoxy group, an aryl group, a substituted heterocyclic ring or a substituted aryl group. The invention also provides an application of the benzo[d]isothiazole-3-(2H)-one derivative in preparation of ischemic stroke treatment medicines.

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.

Evaluation of substituted ebselen derivatives as potential trypanocidal agents

Human African trypanosomiasis is a disease of sub-Saharan Africa, where millions are at risk for the illness. The disease, commonly referred to as African sleeping sickness, is caused by an infection by the eukaryotic pathogen, Trypanosoma brucei. Previously, a target-based high throughput screen revealed ebselen (EbSe), and its sulfur analog, EbS, to be potent in vitro inhibitors of the T. brucei hexokinase 1 (TbHK1). These molecules also exhibited potent trypanocidal activity in vivo. In this manuscript, we synthesized a series of sixteen EbSe and EbS derivatives bearing electron-withdrawing carboxylic acid and methyl ester functional groups, and evaluated the influence of these substituents on the biological efficacy of the parent scaffold. With the exception of one methyl ester derivative, these modifications ablated or blunted the potent TbHK1 inhibition of the parent scaffold. Nonetheless, a few of the methyl ester derivatives still exhibited trypanocidal effects with single-digit micromolar or high nanomolar EC50values.

N-(3-hydroxy-5,7-dimethyladamantan-1-yl)-2-(3-oxobenzo[d]isothiazol-2(3h)-yl)acetamide as a novel inhibitor for staphylococcus aureus sortase a

The present invention relates to a novel sortase A (SrtA) inhibitory compound N-(3-hydroxy-5,7-dimethyladamantan-1-yl)-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide which can be used in medicine as anti-infective agent for treating gram-positive bacterial infection.

N'-(2-(3-oxobenzo[d]isothiazol-2(3h)-yl)acetyl)adamantane-1-carbohydrazide as a novel inhibitor for staphylococcus aureus sortase a

The present invention relates to a novel sortase A (SrtA) inhibitory compound N'-(2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetyl)adamantane-1-carbohydrazide which can be used in medicine as anti-infective agent for treating Gram-positive bacterial infection.

Synthesis of N-(5-aryl-1,3,4-thiadiazol-2-yl)-2-(3-oxo-1,2-benzothiazol- 2(3H)-yl)acetamide derivatives promoted by carbodiimide condensation

Novel N-(5-aryl-1,3,4-thiadiazol-2-yl)-2-(3-oxo-1,2-benzothiazol-2(3H)-yl) acetamide derivatives were prepared by 1-(3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride and N-hydroxybenzotrizole condensation catalysis in a convenient and fast method

1,2-Benzisothiazol-3-one derivatives as a novel class of small-molecule caspase-3 inhibitors

A novel series of 1,2-benzisothiazol-3-one derivatives was synthesized and their biological activities were evaluated for inhibiting caspase-3 and -7 activities, in which some of them showed low nanomolar potency against caspase-3 in vitro and significant protection against apoptosis in a camptothecin-induced Jurkat T cells system. Among the tested compounds, compound 5i exhibited the most potent caspase-3 inhibitory activity (IC50 = 1.15 nM). The molecular docking predicted the interactions and binding modes of the synthesized inhibitor in the caspase-3 active site.

Design, synthesis and characterization of novel 1,2-benzisothiazol-3(2H)- one and 1,3,4-oxadiazole hybrid derivatives: Potent inhibitors of Dengue and West Nile virus NS2B/NS3 proteases

1,2-Benzisothiazol-3(2H)-ones and 1,3,4-oxadiazoles individually have recently attracted considerable interest in drug discovery, including as antibacterial and antifungal agents. In this study, a series of functionalized 1,2-benzisothiazol-3(2H)-one - 1,3,4-oxadiazole hybrid derivatives were synthesized and subsequently screened against Dengue and West Nile virus proteases. Ten out of twenty-four compounds showed greater than 50% inhibition against DENV2 and WNV proteases ([I] = 10 μM). The IC50 values of compound 7n against DENV2 and WNV NS2B/NS3 were found to be 3.75 ± 0.06 and 4.22 ± 0.07 μM, respectively. The kinetics data support a competitive mode of inhibition by compound 7n. Molecular modeling studies were performed to delineate the putative binding mode of this series of compounds. This study reveals that the hybrid series arising from the linking of the two scaffolds provides a suitable platform for conducting a hit-to-lead optimization campaign via iterative structure-activity relationship studies, in vitro screening and X-ray crystallography.