76162-55-5

Upstream product

• 71309-86-9 4-Methoxybenzonitrilsulfid 
• 623-49-4 ethyl cyanoformate 
• 52533-09-2 5-(4-methoxyphenyl)-[1,3,4]oxathiazol-2-one 
• 104478-87-7 5-(p-chlorophenyl)-3-(p-methoxyphenyl)-4-phenyl-4,5-dihydro-1,2,4-thiadiazole 
• 73501-03-8 5-(p-methoxyphenyl)-2,2-bis(trichloromethyl)-1,3,4-oxathiazole 

Downstream Products

• 1068106-46-6 5-hydroxymethyl-3-(4-methoxyphenyl)-1,2,4-thiadiazole 

Relevant academic research and scientific papers

ANTIBACTERIAL AGENTS

Compounds of formula (IA) or (IB) have antibacterial activity: wherein W is =CH- or =N-; Ri and R2 are independently selected from hydrogen, fluoro and chloro, provided that Ri and R2 are not each hydrogen when W is =CH-; n is 0 or 1; X is -O-, -S-, or -C

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.

Heteroarylnitrones as drugs for neurodegenerative diseases: Synthesis, neuroprotective properties, and free radical scavenger properties

New 1,2,4-thiadiazolylnitrones and furoxanylnitrones were developed and evaluated as neuroprotective agents on a human neuroblastoma (SH-SY5Y) cells model. They inhibited at low micromolar concentrations the oxidative damage and the death induced by exposure to hydrogen peroxide. These heteroarylnitrones showed excellent peroxyl free radical absorbance capacities, analyzed by oxygen radical absorbance capacity (ORAC) assay with fluorescein as the fluorescent probe, ranging from 1.5- to 16.5-fold the value of the reference nitrone, α-phenyl-N-tert-butylnitrone (PBN). The electron spin resonance spectroscopy (ESR) demonstrated the ability of these derivatives to directly trap and stabilize oxygen, carbon, and sulfur-centered free radicals. These results demonstrated the potential use of these heteroarylnitrones as neuroprotective agents in preventing the death of cells exposed to enhanced oxidative stress and damage.

Herbicidal [1,2,4] thiadiazoles

Novel herbicidal compounds of the general formula STR1 wherein A represents an optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, aralkyl or heteroaralkyl group; R1 represents a hydrogen atom or an acyl group; an

Nitrile Sulphides. Part 5. 1,3-Dipolar Cycloaddition of p-Methoxybenzonitrile Sulphide to Imines and Crystal Structure of One of the Resulting 4,5-Dihydro-1,2,4-thiadiazoles

p-Methoxybenzonitrile sulphide, generated by thermal fragmentation of the corresponding 1,3,4-oxathiazol-2-one, undergoes 1,3-dipolar cycloaddition to imines forming 4,5-dihydro-1,2,4-thiadiazoles.X-ray crystal structure analysis shows that the heterocyclic ring is non-planar with a fold of 30 deg about the S(1) - N(4) vector.

Nitrile Sulphides. Part 3. Thermal Fragmentation of 1,3,4-Oxathiazoles: Formation of Nitrile Sulphides in a Retro-1,3-dipolar Cycloaddition Reaction

On thermolysis at ca. 160 gradC 1,3,4-oxathiazoles undergo retro-1,3-dipolar cycloaddition forming nitrile sulphides and carbonyl-containing fragments.The nitrile sulphides either decompose to sulphur and nitriles or are trapped as their 1,3-dipolar cycloadducts in the presence of dipolarophiles (dimethyl acetylenedicarboxylate, ethyl cyanoformate, benzonitrile, ethyl propiolate).Similar ratios (1.32, l.34, 1.33, 1.31) of 4- and 5-ethoxycarbonyl-3-(p-methoxyphenyl)isothiazole obtained from four sources of p-methoxybenzonitrile sulphide with ethyl propriolate provide strong evidence for product formation from a discrete intermediate nitrile sulphide rather than via direct interaction of precursor with dipolarophile. 2-Dichloromethylene-1,3,4-oxathiazoles, prepared by dehydrochlorination of 2-trichloromethyloxathiazoles, prepared by dehydrochlorination of 2-trichlorometyloxathiazoles, likewise fragment to nitrile sulphides, but attempts to trap dichloroketene were unsuccessful.

Nitrile Sulphide Formation from the Thermal Fragmentation of 1,3,4-Oxathiazoles: a Retro-1,3-dipolar Cycloaddition

1,3,4-Oxathiazoles, on thermolysis, undergo retro-1,3-dipolar cycloaddition to afford carbonyl compounds and nitrile sulphides, which may be trapped by cycloaddition with alkynes and nitriles.