160982-16-1

Usage

Uses

Used in Pharmaceutical Applications:
(S)-6-CHLORO-1,1-DIOXO-1,2,3,4-TETRAHYDRO-1LAMBDA6-THIENO[3,2-E][1,2]THIAZIN-4-OL is used as a potential pharmaceutical agent for the development of new drugs. Its unique structure may offer novel therapeutic properties, contributing to the advancement of medicine.
Used in Chemical Reactions:
(S)-6-CHLORO-1,1-DIOXO-1,2,3,4-TETRAHYDRO-1LAMBDA6-THIENO[3,2-E][1,2]THIAZIN-4-OL is used as a reagent in chemical reactions. Its distinct molecular composition allows for versatile applications in various chemical processes, facilitating the synthesis of other compounds.
Further research and analysis are necessary to fully understand the properties and potential uses of this chemical compound, as its unique structure may unlock new possibilities in various industries.

InChI:InChI=1/C6H6ClNO3S2/c7-5-1-3-4(9)2-8-13(10,11)6(3)12-5/h1,4,8-9H,2H2/t4-/m1/s1

Upstream product

• 160982-09-2 3-Acetyl-2-(phenylmethyl)thio-5-chlorothiophene 
• 36157-40-1 3-acetyl-2,5-dichlorothiophene 
• 160982-11-6 3-(2-Bromoacetyl)-5-chloro-thiophene-2-sulfonamide 
• 1634-04-4 tert-butyl methyl ether 
• 124-38-9 carbon dioxide 

Downstream Products

• 138890-62-7 brinzolamide 
• 154127-42-1 (S)-3,4-dihydro-4-hydroxy-2(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide 
• 160982-13-8 (S)-3,4-dihydro-6-chloro-4-hydroxy-2-(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide 
• 171273-35-1 2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamine 1,1-dioxide 

Relevant academic research and scientific papers

Enantioselective synthesis of brinzolamide (AL-4862), a new topical carbonic anhydrase inhibitor. The "DCAT Route" to thiophenesulfonamides

A large scale synthesis of the topical carbonic anhydrase inhibitors AL-4623A (13a-HCl) and AL-4862 (13b) from 3-acetyl-2,5-dichlorothiophene ("DCAT", 1) is described. Reaction of 1 with NaSBn gave thioether 2, which was converted via sulfenyl chloride 3 and sulfenamide 5 to sulfonamide 6. Bromination of 6 gave bromo ketone 7, which upon reduction with (+)-B-chlorodiisopinocampheylborane and cyclization of the resulting bromohydrin produced S thieno[3,2-e]-1,2-thiazine 8a (96% ee) after chromatography. Treatment of 8a in THF with -BuLi at -70 °C resulted in Li-Cl exchange. Reaction of the thienyllithium with SO2 and hydroxylamine O-sulfonic acid afforded bis-sulfonamide 11a. Protection of lia as the acetimidate 12a, followed by tosylation and animation, gave R amine 13a. The synthesis of 13b proceeded via primary sulfonamide 16, which was brominated, reduced, and cyclized to give S thieno[3,2-e]-1,2-thiazine 18 (>98% ee). By virtue of the ionizable NH, 18 was separable from reduction byproducts by base extraction. Alkylation of 18 with 3-bromopropyl methyl ether afforded 8b, which was converted as above, via lib, to AL-4862 (13b). These procedures provided multihundred gram lots of 13a and 13b.

Sulfonamides useful as carbonic anhydrase inhibitors

Sulfonamides and pharmaceutical compositions containing the compounds useful in controlling intraocular pressure are disclosed. Methods for controlling intraocular pressure through administration of the compositions are also disclosed.