52188-12-2

Usage

Uses

Used in Chemical Synthesis:
(1,1,3-TRIOXO-1,3-DIHYDRO-1LAMBDA6-BENZO[D]ISOTHIAZOL-2-YL)-ACETONITRILE is utilized as a synthetic intermediate for the creation of various complex organic molecules. Its unique structure and reactivity make it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (1,1,3-TRIOXO-1,3-DIHYDRO-1LAMBDA6-BENZO[D]ISOTHIAZOL-2-YL)-ACETONITRILE is employed as a key building block for the development of novel drug candidates. Its presence in molecular structures can contribute to the modulation of biological targets, potentially leading to new treatments for a variety of diseases.
Used in Material Science:
(1,1,3-TRIOXO-1,3-DIHYDRO-1LAMBDA6-BENZO[D]ISOTHIAZOL-2-YL)-ACETONITRILE's chemical properties also make it suitable for use in material science, where it can be incorporated into the design of new materials with specific properties, such as improved stability, conductivity, or responsiveness to environmental stimuli.
Used in Research and Development:
(1,1,3-TRIOXO-1,3-DIHYDRO-1LAMBDA6-BENZO[D]ISOTHIAZOL-2-YL)-ACETONITRILE is used as a research tool in academic and industrial laboratories. It aids scientists in understanding the fundamental chemical and biological interactions of benzo[d]isothiazole derivatives, which can inform the design of new molecules with tailored properties for specific applications.

InChI:InChI=1/C9H6N2O3S/c10-5-6-11-9(12)7-3-1-2-4-8(7)15(11,13)14/h1-4H,6H2

Upstream product

• 128-44-9 saccharin sodium salt 
• 590-17-0 cyanomethyl bromide 
• 107-14-2 chloroacetonitrile 
• 81-07-2 saccharin 
• 77697-00-8 3-oxo-1,2-benzoisothiazoline-2-(N,N-diethyl)acetamide 1,1-dioxide 

Downstream Products

• 99943-09-6 o-carbomethoxy-N-cyanomethylbenzenesulfonamide 

Relevant academic research and scientific papers

Synthesis, antifungal evaluation and molecular docking studies of some tetrazole derivatives

A facile and simple protocol for the [3+2] cycloaddition of alkyl nitriles (RCN) with sodium azide (NaN3) in the presence of copper bis(diacetylcurcumin) 1,2-diamin-obenzene Schiff base complex, SiO2-[Cu-BDACDABSBC] as a heterogeneous catalyst in the presence of ascorbic acid and a solution of water/i-PrOH (50:50, V/V) media at reflux condition is described. The supported catalyst was prepared by immobilization of a copper bis(diacetylcurcumin) 1,2-diaminobenzene Schiff base complex [Cu-BDACDABSBC] on silica gel. The complex has high selectivity, catalytic activity, and recyclability. The significant features of this procedure are high yields, broad substrate scope and simple and efficient work-up procedure. According to this synthetic methodology, excellent yields of 5-substituted 1H-tetrazoles having bioactive N-heterocyclic cores were synthesized. The in vitro antifungal activities of title compounds were screened against various pathogenic fungal strains, such as Candida species involving C. albicans, C. glabrata, C. krusei, C. parapsilosis as well as filamentous fungi like Aspergillus species consisting of A. fumigatus and A. flavus. The molecular docking analysis is discussed for one most potent compound against fungi. The docking study determined a remarkable interaction between the most potent compounds and the active site of Mycobacterium P450DM.

An efficient protocol for facile synthesis of new 5-substituted-1H-tetrazole derivatives using copper-doped silica cuprous sulfate (CDSCS) as heterogeneous nano-catalyst

A facile and highly efficient protocol for synthesis of new 5-substituted-1H-tetrazoles derivatives using copper-doped silica cuprous sulfate (CDSCS) is described. In this method, the cycloaddition reaction of sodium azide with structurally diverse nitriles involving bioactive N-heterocyclic cores exploiting CDSCS in refluxing H2O/i-PrOH (1:1, v/v) furnishes the corresponding 5-substituted-1H-tetrazoles in good to excellent yields (up to 93percent). The influence of parameters effective in progress of reaction including solvent type, temperature and catalyst was studied and discussed. In this protocol, CDSCS was proved to be an efficient heterogeneous nano-catalyst to easily achieve the new tetrazole derivatives. The advantages of CDSCS in current protocol known are its cheapness, thermal and chemical stability, ease of recyclability and reusability for several consecutive runs without significant decline in its reactivity.

Cu/Graphene/Clay Nanohybrid: A Highly Efficient Heterogeneous Nanocatalyst for Synthesis of New 5-Substituted-1H-Tetrazole Derivatives Tethered to Bioactive N-Heterocyclic Cores

A series of new 5-substituted 1H-tetrazoles bearing bioactive N-heterocyclic cores were synthesized through [3 + 2] cycloaddition reactions between alkyl nitriles (RCN) and NaN3in the presence of Cu/aminoclay/reduced graphene oxide nanohybrid (Cu/AC/r-GO nanohybrid) as a heterogeneous nanocatalyst in water/i-PrOH (50:50, V/V) media at reflux condition. The influence of factors on a sample reaction including solvent type, temperature, and catalyst amount was discussed. This current protocol has many advantages including inexpensiveness, environmentally benign, broad substrate scope, excellent yields, and easy work-up procedure. The Cu/AC/r-GO used in this protocol is a low-cost catalyst that proved to have considerable chemical and thermal stabilities. This non-hygroscopic catalyst can be easily recycled, reused, and stored for many consecutive reaction runs without significant loss in its reactivity.

Design, synthesis and evaluation of N-substituted saccharin derivatives as selective inhibitors of tumor-associated carbonic anhydrase XII

A series of N-alkylated saccharin derivatives were synthesized and tested for the inhibition of four different isoforms of human carbonic anhydrase (CA, EC 4. 2.1.1): the transmembrane tumor-associated CA IX and XII, and the cytosolic CA I and II. Most of the reported derivatives inhibited CA XII in the nanomolar/low micromolar range, hCA IX with KIs ranging between 11 and 390 nM, whereas they were inactive against both CA I (KIs >50 μM) and II (KIs ranging between 39.1 nM and 50 μM). Since CA I and II are off-targets of antitumor carbonic anhydrase inhibitors (CAIs), the obtained results represent an encouraging achievement for the development of new anticancer candidates without the common side effects of non-selective CAIs. Moreover, the lack of an explicit zinc binding function on these inhibitors opens the way towards the exploration of novel mechanisms of inhibition that could explain the high selectivity of these compounds for the inhibition of the transmembrane, tumor-associated isoforms over the cytosolic ones.

Pseudosaccharin amine derivatives: Synthesis and elastase inhibitory activity

Pseudosaccharin amines were synthesized from saccharin either by the reaction of pseudosaccharin chloride with amines, or via thiosaccharin which was treated with amines yielding thiosaccharinates, and their reaction with glacial acetic acid. This route gave lower yields than the first way. The synthesis of alkyl [(1,1-dioxo-benzo[d]isothiazol-3-yl)amino]alkanoates as possible Human Leukocyte Elastase (HLE) inhibitors was realized by the reaction between amino acid esters and pseudosaccharin chloride. Hydrolysis of the esters was possible under aqueous basic conditions. Selected compounds were screened for elastase inhibitory activity. Compounds 4k and 4m were found to be reversible inhibitors of HLE with Ki values of 45 μM and 60 μM.

Mechanism of Hydrolysis of O-Imidomethyl Derivatives of Phenols

Three series of O-imidomethyl derivatives of para-substituted phenolic compounds were synthesized and their rates of hydrolysis were studied.Saccharin, phthalimide, and succinimide served as the imide portions of the derivatives.Their rates of hydrolysis were found to be first order with respect to hydroxide from pH 7.0 to 10 or 11 and dependent on the acidity (leaving group potential) of both the imide and the phenol portions.The more acidic the imide or the phenol, the faster the rate of hydrolysis.However, the rates of hydrolysis were more sensitive to the acidity of the phenol.Trapping experiments with cyanide also suggested that the phenol anion was functioning as the leaving group in what is apparently an SN2 reaction.An amide derivative was found to hydrolyze more slowly than predicted from the analogous series and the pKa of the amide.This result is apparently due partially stereoelectronic constraints in the imide series that cause the CH2-O bond to be oriented more nearly perpendicular to the plane of the C(=O)N group and hence more accessible to nucleophilic attack.

13C NMR Analysis of some 4-Hydroxy-2H-1,2-benzothiazine 1,1-Dioxides

The 13C nmr spectra of some 4-hydroxy-2H-1,2-benzothiazine 1,1-dioxides I have been recorded and analyzed.Spectroscopic assignments were made on the basis of chemical shift theory, APT and fully coupled 13C nmr spectra.Spectral data support the enolic structure of these compounds.