5393-55-5

Usage

Uses

Used in Pharmaceutical Industry:
CL 19506 7-5526 is used as an impurity reference for [application reason] the quality control and assurance of Acetazolamide (A161500).
This is important because it helps ensure the safety, efficacy, and purity of the drug, which is crucial for patient health and compliance.

InChI:InChI=1/C4H5N3OS/c1-3(8)6-4-7-5-2-9-4/h2H,1H3,(H,6,7,8)

Upstream product

• 41030-51-7 1-ethoxymethylene thiosemicarbazide 
• 108-24-7 acetic anhydride 
• 2302-84-3 1-formylthiosemicarbazide 
• 75-36-5 acetyl chloride 
• 4005-51-0 [1,3,4]Thiadiazol-2-ylamin 

Downstream Products

• 4005-51-0 [1,3,4]Thiadiazol-2-ylamin 
• 55114-97-1 N-(5-bromo-1,3,4-thiadiazol-2-yl)-acetamide 

Relevant academic research and scientific papers

Synthesis and crystal structure of 2-aminoacetyl-1,3,4-thiadiazole

2-Aminoacetyl-1,3,4-thiadiazole was synthesized, and its structure was studied. In crystal, the thiadiazole molecules form hydrogen-bonded endless one-dimensional chains related by the glide reflection plane.

Acetazolamide-based fungal chitinase inhibitors

Chitin is an essential structural component of the fungal cell wall. Chitinases are thought to be important for fungal cell wall remodelling, and inhibition of these enzymes has been proposed as a potential strategy for development of novel anti-fungals. The fungal pathogen Aspergillus fumigatus possesses two distinct multi-gene chitinase families. Here we explore acetazolamide as a chemical scaffold for the inhibition of an A. fumigatus 'plant-type' chitinase. A co-crystal structure of AfChiA1 with acetazolamide was used to guide synthesis and screening of acetazolamide analogues that yielded SAR in agreement with these structural data. Although acetazolamide and its analogues are weak inhibitors of the enzyme, they have a high ligand efficiency and as such are interesting leads for future inhibitor development.

1H, 13C, 15N and19F NMR study of acetylation products of heterocyclic thiosemicarbazones

Novel 2-acetylamino-4-acetyl-5-aryl(heteryl)-1,3,4-thiadiazolines, 2-acetylamino-5-aryl(heteryl)-1,3,4-thiadiazoles, and some of their salts were prepared and studied by multinuclear 1H, 13C, 15N, 19F and 2D NMR

GIAO/DFT 13C NMR Chemical Shifts of 1,3,4-thiadiazoles

1H, 13C and 15N NMR spectra of 2-acetylamino-1,3,4-thiadiazole and its 5-substituted derivatives have been measured and assigned based on reference data, as well as homo- and heteronuclear 2 D NMR experiments. In addition, the GIAO/DFT approach at the B3LYP level of theory using the 6-311G basis set was used to calculate the 13C NMR chemical shifts. Although this method gives reliable results for 2-arylhydrazones of 1,3-diphenylpropanetrione, 2-phenacylpyridines, (Z)-2-(2-hydroxy-2-phenylvinyl)pyridines, 4-fluoroanilines, (1Z,3Z)-1,4-di(pyridin-2-yl)buta-1,3-dienediols and their tautomeric forms, the calculated chemical shifts for the 1,3,4-thiadiazoles studied are less satisfactory. Presence of the sulfur atom(s) seems to be responsible for such behavior.

Synthesis, oxidation and dehydrogenation of cyclic N,O- and N,S-acetals. Part 1. Transformation of N,S-acetals: 3-acyl-1,3,4-thiadiazolines

Aldehyde and ketone thiosemicarbazones are synthesized and cyclized into 3-acyl-1,3,4-thiadiazolines under acylating conditions. Reactions of the 2-monosubstituted heterocycles with oxidizing and dehydrogenating agents (KMnO4 or for the first time with CAN, DDQ, IBDA) lead to the formation of thiadiazoles. CAN oxidation of 2,2-disubstituted 3-acyl-1,3,4-thiadiazolines regenerates the parent ketones efficiently.