821806-22-8

Basic information

• Product Name: Carbamic acid, [2-[(cyanomethyl)sulfonyl]-5-(trifluoromethyl)phenyl]-, ethyl ester
• CAS NO: 821806-22-8
• Molecular Formula: C12H11F3N2O4S
• Molecular Weight: 336.292
• Mol File: 821806-22-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [2-[(cyanomethyl)sulfonyl]-5-(trifluoromethyl)phenyl]-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [2-[(cyanomethyl)sulfonyl]-5-(trifluoromethyl)phenyl]-, ethyl ester(821806-22-8)
• EPA Substance Registry System: Carbamic acid, [2-[(cyanomethyl)sulfonyl]-5-(trifluoromethyl)phenyl]-, ethyl ester(821806-22-8)

Safety Data

• Hazardous Substances Data: 821806-22-8(Hazardous Substances Data)

Upstream product

• 4274-38-8 2-amino-4-(trifluoromethyl)benzenethiol hydrochloride 
• 293316-23-1 (2-amino-4-trifluoromethylphenylsulfanyl)acetonitrile 

Relevant articles and documents

Synthesis and pharmacological evaluation of 4H-1,4-benzothiazine-2- carbonitrile 1,1-dioxide and N-(2-cyanomethylsulfonylphenyl)acylamide derivatives as potential activators of ATP sensitive potassium channels

1,2,4-Thiadiazine derivatives, like 3-methyl-7-chlorobenzo-4H-1,2,4- thiadiazine 1,1-dioxide, diazoxide and 7-chloro-3-isopropylamino-4H-benzo-1,2,4- thiadiazine 1,1-dioxide, BPDZ 73, are potent openers of Kir6.2/SUR1 K ATP channels. To explore the structure-activity relationship of this series of KATP openers, 4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide and N-(2-cyanomethylsulfonylphenyl)acylamide derivatives were synthesized from 2-acetylamino-5-chloro-benzenesulfonic acid pyridinium salt or 2-aminobenzenethiols. The 4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide derivatives (e.g., 7-chloro-3-isopropylamino-4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide, 3f) were found to activate KATP channels as indicated by their ability to hyperpolarize beta cell membrane potential, to inhibit glucose-stimulated insulin release in vitro and to increase ion currents through Kir6.2/SUR1 channel as measured by patch clamp. The potency and efficacy of, for example, 3f is however significantly reduced compared to the corresponding 4H-1,2,4-benzothiadiazine 1,1-dioxide derivatives. Opening of the 4H-1,2,4-thiadiazine ring to get (e.g., 2-cyanomethylsulfonyl-4-fluorophenyl) carbamic acid isopropyl ester (4c) gives rise to compounds, which are able to open KATP channels but with considerable reduced potency compared to, for example, diazoxide. Compound 3a, 7-chloro-3-methyl-4H-1,4-benzothiazine-2- carbonitrile 1,1-dioxide, which inhibits insulin release in vitro from beta cells and rat islets, reduces plasma insulin levels and blood pressure in anaesthetized rats upon intravenous administration.