452-35-7 Usage
Description
6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE is a chemical compound with the molecular formula C8H8N2O3S. It belongs to the class of benzothiazolesulfonamide derivatives and is characterized by the presence of an ethoxy group at the 6-position and a sulfonamide group at the 2-position. 6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE exhibits various biological activities and has potential applications in different fields.
Uses
Used in Pharmaceutical Industry:
6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE is used as an alcohol dehydrogenase inhibitor for its ability to inhibit the enzyme alcohol dehydrogenase, which plays a crucial role in the metabolism of alcohol. This inhibition can help in the treatment of alcohol-related disorders and reduce the harmful effects of alcohol consumption.
6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE is also used as an antidote in cases of poisoning or overdose. Its ability to inhibit certain enzymes and interfere with metabolic pathways can help counteract the toxic effects of certain substances and provide relief to the affected individual.
Used in Ophthalmology:
In the treatment of glaucoma, 6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE is used as a carbonic anhydrase inhibitor. Carbonic anhydrase enzymes are involved in the production of aqueous humor in the eye, and their inhibition can help reduce intraocular pressure, a key factor in glaucoma management.
Additionally, 6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE is used as a diuretic, promoting the excretion of excess water and salts from the body. This can help in the management of conditions like edema and high blood pressure, contributing to overall cardiovascular health.
Originator
Cardrase,Upjohn,US,1957
Manufacturing Process
Preparation of 6-Ethoxybenzothiazole-2-Sulfenamide: A solution prepared by
dissolving 21.0 grams (0.1 mol) of 6-ethoxybenzothiazole-2-thiol, Sebrell and
Boord, J. Am. Chem. Soc. 45: 2390 to 2399 (1923), in 75 ml of water
containing 5 grams of sodium hydroxide, and 75 ml of 10% sodium
hypochlorite solution were added simultaneously to 300 ml of concentrated
ammonium hydroxide which was cooled to 0°C, and vigorously stirred. During the addition the temperature was not allowed to rise above 5°C. The resulting
solid was recovered by filtration, washed thoroughly with water, and dried at
room temperature under reduced pressure. There was obtained 21 grams of
6-ethoxybenzothiazole-2-sulfenamide melting at 132° to 155°C
(decomposition). Recrystallization from ethyl acetate gave a product melting
at 140.5° to 143°C (decomposition).Preparation of 6-Ethoxybenzothiazole-2-Sulfonamide: A solution of 3.39 grams
(0.015 mol) of the sulfenamide in 100 ml of acetone was treated dropwise,
with stirring, with a solution of 3.5 grams of potassium permanganate in 100
ml of water. The temperature rose to 42°C. After stirring an additional 10
minutes the reaction mixture was filtered to remove manganese dioxide, the
latter was washed with 100 ml of warm water, and the combined filtrates were
concentrated under reduced pressure to remove acetone. The residual solution
was treated with charcoal, filtered and acidified with concentrated hydrochloric
acid. After standing in the refrigerator for 4 hours the solid sulfonamide was
recovered by filtration, washed with water and dried. There was obtained 2.37
grams of 6-ethoxybenzothiazole-2-sulfonamide melting at 180° to 190°C.
Recrystallization from ethyl acetate-Skellysolve B gave 1.25 grams of material
melting at 188° to 190.5°C.
Clinical Use
Ethoxzolamide is another carbonic anhydrase inhibitor with properties and uses resembling those of acetazolamide.
Check Digit Verification of cas no
The CAS Registry Mumber 452-35-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,5 and 2 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 452-35:
(5*4)+(4*5)+(3*2)+(2*3)+(1*5)=57
57 % 10 = 7
So 452-35-7 is a valid CAS Registry Number.
InChI:InChI=1/C9H10N2O3S2/c1-2-14-6-3-4-7-8(5-6)15-9(11-7)16(10,12)13/h3-5H,2H2,1H3,(H2,10,12,13)
452-35-7Relevant articles and documents
COMPOUNDS AND COMPOSITIONS FOR USE IN AUGMENTATION OF GLUCOSE UPTAKE AND INSULIN SECRETION
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, (2013/03/26)
The present invention is directed to compounds such as: formula wherein linker is independently selected from the group consisting of -S-, -S-S-, -S-(CH2)n-, -NH-, -NH-(CH2)n-, -0-, -S02-, arylene, heteroarylene; Rl is selected from the group consisting of straight or branched C4- C20 alkyl, straight or branched C4-C20 alkenyl, straight or branched C4-C20 alkynyl, each optionally interrupted with at least one NH, C5- C7 saturated cycloalkyl or heteroalkyl ring, C5-C12 aromatic or het- eroaromatic ring, each optionally substituted with at least one group selected from -COOH, -NH2, C1-C8 alkoxy, C1-C5 amidyle, C1-C5 car- boxyl, halogen; and R2 is independently selected from the group consisting of H, OH, SH, NH2, N02, halogen, CN, C1-C8 alkoxy, C1-C5 carboxylic acid, straight or branched C1-C8 alkyl, straight or branched C2-C10 alkenyl, straight or branched C2 - C12 alkynyl each optionally substituted by at least one substituent selected from the group consisting of C1-C5 alkoxy, C1-C5 carboxylic acid, OH, SH, NH2, halogen; and compositions for use in the treatment of diabetes and related dis? orders.
Topically active ocular benzothiazole sulfonamide carbonic anhydrase inhibitors
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, (2008/06/13)
This invention is directed to compounds of the formula STR1 and pharmaceutically acceptable salts thereof wherein R6 is hydrogen or lower alkyl; each R1 is hydrogen, lower alkyl, halogen, nitro, trihaloalkyl, lower alkoxy, formyl, lower alkanoyl, loweralkylamino or diloweralkylamino STR2 X is O, S or NR5 ; R2 is OR7 or NR7 R8 ; each R3 and R4 are independently hydrogen or lower alkyl; R5 R7 and R8 are independently hydrogen or lower alkyl; n is 0-3 and m is 0-6. These compounds are useful for treating glaucoma or assessing corneal function in mammals.
IMPROVED OXIDATION OF THE SULFENAMIDE FUNCTIONALITY: EFFICIENT SYNTHESIS OF 6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE
Larsen, R.D.,Roberts, F.E.
, p. 899 - 904 (2007/10/02)
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