217972-52-6

Basic information

• Product Name: N-[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]-beta-alanine trifluoroacetate
• CAS NO: 217972-52-6
• Molecular Formula: C₅H₉N₅O₃S₂
• Molecular Weight: 365.31145
• Mol File: 217972-52-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]-beta-alanine trifluoroacetate(CAS DataBase Reference)
• NIST Chemistry Reference: N-[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]-beta-alanine trifluoroacetate(217972-52-6)
• EPA Substance Registry System: N-[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]-beta-alanine trifluoroacetate(217972-52-6)

Safety Data

• Hazardous Substances Data: 217972-52-6(Hazardous Substances Data)

Upstream product

• 1355987-21-1 C₂₀H₁₉N₅O₅S₂ 
• 227196-53-4 [2-(5-sulfamoyl-[1,3,4]thiadiazol-2-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 

Downstream Products

• 729-46-4 4,4'-(dithiodicarbonothioyl)dimorpholine 
• 137-26-8 Thiram 

Relevant articles and documents

Carbonic anhydrase inhibitors - Part 78. Synthesis of water-soluble sulfonamides incorporating β-alanyl moieties, possessing long lasting- intraocular pressure lowering properties via the topical route

Reaction of 26 aromatic/heterocyclic sulfonamides containing amino, imino, hydrazino or hydroxyl groups with N-tert-butyloxycarbonyl-β-alanine (Boc-β-ala; Boc = t-butoxycarbonyl) in the presence of carbodiimide derivatives afforded, after removal of the protecting group, a series of water-soluble compounds (as salts of strong acids, such as hydrochloric, trifluoroacetic or trifluoromethane sulfonic). The new derivatives were assayed as inhibitors of the zinc enzyme carbonic anhydrase (CA), and more precisely of three of its isozymes, CA I, II (cytosolic forms) and IV (membrane-bound form), involved in important physiological processes. Good inhibition was observed against all three isozymes, but especially against CA II and CA IV (in the nanomolar range), the two isozymes known to play a critical role in aqueous humour secretion within the ciliary processes of the eye. Some of the best inhibitors synthesized were applied as 2% aqueous solutions into the eyes of normotensive or glaucomatous albino rabbits, when strong and long-lasting intraocular pressure (IOP) lowering was observed with many of them. Thus, the amino acyl groups conferring water solubility to these sulfonamide CA inhibitors, coupled with their strong enzyme inhibitory properties and balanced lipid solubility seem to be the key factors for obtaining compounds with effective topical antiglaucoma activity. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

CARBONIC ANHYDRASE TARGETING AGENTS AND METHODS OF USING SAME

The invention provides agents that target carbonic anhydrase, which can be used as imaging agents or therapeutic agents. The agents can be used to image tumor hypoxia as well as other physiological processes in a subject.