50483-79-9

Basic information

• Product Name: ethyl 3-phenyl-1,2,4-thiadiazole-5-carboxylate
• Synonyms: ethyl 3-phenyl-1,2,4-thiadiazole-5-carboxylate;3-Phenyl-1,2,4-thiadiazole-5-carboxylic acid ethyl ester
• CAS NO: 50483-79-9
• Molecular Formula: C₁₁H₁₀N₂O₂S
• Molecular Weight: 234.2743
• Mol File: 50483-79-9.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ethyl 3-phenyl-1,2,4-thiadiazole-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-phenyl-1,2,4-thiadiazole-5-carboxylate(50483-79-9)
• EPA Substance Registry System: ethyl 3-phenyl-1,2,4-thiadiazole-5-carboxylate(50483-79-9)

Safety Data

• Hazardous Substances Data: 50483-79-9(Hazardous Substances Data)

Upstream product

• 57459-16-2 (3-phenyl-[1,2,4]thiadiazol-5-yl)-ethenetricarbonitrile 
• 5852-49-3 5-phenyl-1,3,4-oxathiazol-2-one 
• 623-49-4 ethyl cyanoformate 
• 73501-00-5 5-phenyl-2-trichloromethyl-1,3,4-oxathiazole 
• 2362-05-2 benzonitrile sulphide 
• 55-21-0 benzamide 
• 74466-89-0 5-Phenyl-1,2,4-thiadiazole 
• 50483-82-4 3-phenyl-1,2,4-thiadiazole 

Downstream Products

• 50483-82-4 3-phenyl-1,2,4-thiadiazole 
• 138128-76-4 5-(hydroxymethyl)-3-phenyl-1,2,4-thiadiazole 
• 138129-05-2 [4-Oxo-3-(3-phenyl-[1,2,4]thiadiazol-5-ylmethyl)-3,4-dihydro-phthalazin-1-yl]-acetic acid ethyl ester 
• 138129-12-1 [4-Oxo-3-(3-phenyl-[1,2,4]thiadiazol-5-ylmethyl)-3,4-dihydro-phthalazin-1-yl]-acetic acid 
• 138128-82-2 5-(bromomethyl)-3-phenyl-1,2,4-thiadiazole 

Relevant articles and documents

THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE

Provided are compounds useful for treating cancer and methods of treating cancer comprising administering to a subject in need thereof a compound described herein.

Microwave-induced generation and reactions of nitrile sulfides: An improved method for the synthesis of isothiazoles and 1,2,4-thiadiazoles

The 1,3-dipolar cycloaddition reactions of nitrile sulfides, generated by microwave-assisted decarboxylation of 1,3,4-oxathiazol-2-ones, have been investigated. By this approach ethyl 1,2,4-thiadiazole-5-carboxylates 3 were prepared in good yield by cycloaddition of the nitrile sulfides to ethyl cyanoformate. Similarly, reaction of benzonitrile sulfide with dimethyl acetylenedicarboxylate (DMAD) afforded dimethyl 3-phenylisothiazole-4,5- dicarboxylate (5). In contrast, o-hydroxybenzonitrile sulfide, generated from the corresponding oxathiazolone 2d, reacted with DMAD to give methyl 4-oxo-4H-[1]benzopyrano[4,3-c]isothiazole-3-carboxylate (8) in high yield. A ca. 1:1 mixture of ethyl 3-phenylisothiazole-4- and 5-carboxylates (6,7) was formed from benzonitrile sulfide and ethyl propiolate. The corresponding reaction with diethyl fumarate gave diethyl trans-4,5-dihydro-3-phenylisothiazole-4,5- dicarboylate (10). 3-Arylisothiazoles, unsubstituted at both the 4- and 5-positions, were prepared from the reaction of 5-aryl-1,3,4-oxathiazolones with norbornadiene by a pathway involving cycloaddition of the nitrile sulfide to the norbornadiene, followed by retro-Diels-Alder extrusion of cyclopentadiene from the resulting isothiazoline cycloadduct 12. In summary, the use of microwave irradiation, rather than conventional heating methods, allows nitrile sulfide generation and reactions to be carried out in shorter times, with easier work-up and, in some cases, in higher yields.

Non-ATP competitive glycogen synthase kinase 3β (GSK-3β) inhibitors: Study of structural requirements for thiadiazolidinone derivatives

The 2,4-disubstituted thiadiazolidinones (TDZD) were described as the first non-ATP competitive GSK-3β inhibitors. New modifications in this heterocyclic ring are here reported to study the influence on the biological activity. The basic skeleton of 1,2,4-thiadiazole and also one of the carbonyl groups are kept, while different modifications are introduced in positions 3 and 5, respectively. The GSK-3β activity of the new thiadiazole derivatives here synthesized showed IC50 values for some of the compounds in the micromolar range. Additionally, ATP competition studies have been carried out, showing that as well as the first generation of TDZD, these new compounds act in a non-competitive manner. With this study, additional requirements for the biological activity of the TDZD family have been delineated.