452-35-7 Usage
Originator
Cardrase,Upjohn,US,1957
Uses
Different sources of media describe the Uses of 452-35-7 differently. You can refer to the following data:
1. alcohol dehydrogenase inhibitor, antidote
2. Ethoxzolamide is used in the treatment of glaucoma, and is also used as a diuretic, acting as a carbonic anhydrase inhibitor.
Definition
ChEBI: 1,3-Benzothiazole substituted a sulfonamide and an ethoxy group at positions 2 and 6, respectively. A carbonic anhydrase inhibitor, it has been used in the treatment of glaucoma, and as a diuretic.
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.
General Description
6-Ethoxy-2-benzothiazolesulfonamide is a membrane permeable carbonic anhydrase inhibitor and its ocular disposition and pharmacology in normal albino rabbits has been investigated. It causes inhibition of insulin degradation in vitro.
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
-
Page/Page column 28, (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
-
, (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)
-
