892248-34-9

Basic information

• Product Name: 2-(4-Bromo-phenyl)-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one
• Synonyms: 2-(4-Bromo-phenyl)-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one
• CAS NO: 892248-34-9
• Molecular Weight: 338.181
• Mol File: 892248-34-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(4-Bromo-phenyl)-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Bromo-phenyl)-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one(892248-34-9)
• EPA Substance Registry System: 2-(4-Bromo-phenyl)-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one(892248-34-9)

Safety Data

• Hazardous Substances Data: 892248-34-9(Hazardous Substances Data)

Upstream product

• 81-07-2 saccharin 
• 35812-01-2 N-bromosaccharin 
• 108-86-1 bromobenzene 
• 81-08-3 2-sulfobenzoic acid cyclic anhydride 
• 106-40-1 4-bromo-aniline 
• 26638-43-7 2-methoxycarbonylbenzenesulfonyl chloride 
• 1026896-85-4 2-(4-Bromo-phenylsulfamoyl)-benzoic acid methyl ester 

Downstream Products

• 1028259-71-3 C₁₈H₁₃BrN₂O₆S 
• 1026308-58-6 [2-(4-Bromo-phenyl)-3-cyano-1,1-dioxo-2,3-dihydro-1H-1λ⁶-benzo[d]isothiazol-3-yl]-cyano-acetic acid ethyl ester 

Relevant articles and documents

Novel insights on saccharin- and acesulfame-based carbonic anhydrase inhibitors: design, synthesis, modelling investigations and biological activity evaluation

A large library of saccharin and acesulfame derivatives has been synthesised and evaluated against four isoforms of human carbonic anhydrase, the two off-targets hCA I/II and the tumour related isoforms hCA IX/XII. Different strategies of scaffold modification have been attempted on both saccharin as well as acesulfame core leading to the obtainment of 60 compounds. Some of them exhibited inhibitory activity in the nanomolar range, albeit some of the performed changes led to either micromolar activity or to its absence, against hCA IX/XII. Molecular modelling studies focused the attention on the binding mode of these compounds to the enzyme. The proposed inhibition mechanism is the anchoring to zinc-bound water molecule. Docking studies along with molecular dynamics also underlined the importance of the compounds flexibility (e.g. achieved through the insertion of methylene group) which favoured potent and selective hCA inhibition.

Novel Spirosuccinimides with Incorporated Isoindolone and Benzisothiazole 1,1-Dioxide Moieties as Aldose Reductase Inhibitors and Antihyperglycemic Agents

Compounds from two novel series of spirosuccinimides were prepared.Analogs of series 2 possessed a spiro-fused isoindolone moiety while those of series 3 contained a spiro-fused benzisothiazole S,S-dioxide group.These compounds were evaluated as aldose reductase inhibitors (ARI) in vitro by their ability to inhibit glyceraldehyde reduction using a partially purified bovine lens aldose reductase preparation and in vivo as inhibitors of galactitol accumulation in the lens, sciatic nerve, and diaphragm of galactose-fed rats.Many members from the isoindolone series 2,particularly those containing an isoindolone N-methyl moiety, showed good in vitro and in vivo potency.The most potent member, the 6-chloro analog 32, was resolved, and aldose reductase activity was found to reside almost exclusively in the (+)-enantiomer.Compound 32 was approximately equipotent in the sciatic nerve of the galactose-fed rat to other cyclic imide ARI's of similar in vitro activity, namely sorbinil and ADN-138 and also to tolrestat, an acetic acid-based ARI (ED50's 4-8 mg/kg).Compounds from both series, 2 and 3, were also found to lower plasma glucose levels of genetically obese db/db and ob/ob mice with potency similar to that of ciglitazone.However, members from these series failed to lower insulin levels of the ob/ob mouse at the doses tested.