821806-26-2

Basic information

• Product Name: Acetonitrile, [(2-amino-5-chlorophenyl)thio]-
• CAS NO: 821806-26-2
• Molecular Formula: C8H7ClN2S
• Molecular Weight: 198.676
• Mol File: 821806-26-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Acetonitrile, [(2-amino-5-chlorophenyl)thio]-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetonitrile, [(2-amino-5-chlorophenyl)thio]-(821806-26-2)
• EPA Substance Registry System: Acetonitrile, [(2-amino-5-chlorophenyl)thio]-(821806-26-2)

Safety Data

• Hazardous Substances Data: 821806-26-2(Hazardous Substances Data)

Upstream product

• 23474-98-8 2-amino-5-chlorobenzenethiol 
• 107-14-2 chloroacetonitrile 
• 95-24-9 6-chloro-2-aminobenzothiazole 

Downstream Products

• 81836-62-6 3-amino-7-chloro-2H-1,4-benzothiazine 
• 108176-75-6 N-(7-chloro-2H-1,4-benzothiazin-3-yl)-N'-(2,6-dimethylphenyl)urea 
• 108176-74-5 N-(7-chloro-2H-1,4-benzothiazin-3-yl)-N'-(3,4-dichlorophenyl)urea 
• 108176-72-3 N-(7-chloro-2H-1,4-benzothiazin-3-yl)-N'-(4-methoxyphenyl)urea 
• 108176-73-4 N-(7-chloro-2H-1,4-benzothiazin-3-yl)-N'-(4-chlorophenyl)urea 
• 108176-71-2 N-(7-chloro-2H-1,4-benzothiazin-3-yl)-N'-phenylurea 
• 821806-21-7 (4-chloro-2-cyanomethanesulfonyl-phenyl)-carbamic acid ethyl ester 
• 821806-23-9 (4-chloro-2-cyanomethylsulfanylphenyl)carbamic acid ethyl ester 

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.