59834-06-9

Usage

Structure

Heterocyclic aromatic compound with a thiadiazole ring and a phenol group

Common uses

Building block in the synthesis of pharmaceuticals and agrochemicals

Potential applications

Materials science and organic chemistry

Ongoing research

Exploration of its potential uses and effects

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 59834-04-7 N'-[1-(2-hydroxy-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl ester 
• 59834-04-7 [1-(2-hydroxy-phenyl)-ethylidene]-carbazic acid ethyl ester 

Downstream Products

• 36724-16-0 2-(methylsulfanyl)benzofuran 
• 854372-33-1 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzylsulfanyl]benzofuran 
• 1165761-33-0 dodecylcarbamic acid 2-(1,2,3-thiadiazol-4-yl)phenyl ester 
• 1165761-28-3 n-butylcarbamic acid 2-(1,2,3-thiadiazol-4-yl)phenyl ester 
• 66355-56-4 2-Benzofuranthiol 
• 89406-33-7 2-(1,2,3-Thiadiazol-4-yl)phenyl isocyanatosulfonate 

Relevant academic research and scientific papers

Synthesis method of 1, 2, 3-thiadiazole derivative

The invention belongs to the technical field of compound preparation, and discloses a synthesis method of a 1, 2, 3-thiadiazole derivative. The synthesis method of the 1, 2, 3-thiadiazole derivative comprises the following steps: taking an N-tosylhydrazon

Diiiodine/Potassium Persulfate Mediated Synthesis of 1,2,3-Thiadiazoles from N -Tosylhydrazones and a Thiocyanate Salt as a Sulfur Source under Transition-Metal-Free Conditions

A highly efficient method for the synthesis of 1,2,3-thiadiazoles has been developed by utilizing readily available tosylhydrazones and ammonium thiocyanate with ecofriendly EtOH as the solvent at room temperature. The reaction shows a wide scope of subst

I2/CuCl2-promoted one-pot three-component synthesis of aliphatic or aromatic substituted 1,2,3-thiadiazoles

An efficient I2/CuCl2-promoted one-pot three-component strategy for the construction of 1,2,3-thiadiazoles from aliphatic- or aromatic-substituted methyl ketones, p-toluenesulfonyl hydrazide, and potassium thiocyanate has been develo

Synthesis of benzo[b]furan-2-thioles from 4-(2-Hydroxyaryl)-1,2,3- thiadiazoles

4-(2-Hydroxyaryl)-1,2,3-thiadiazoles treated with bases decompose with nitrogen liberation and the formation of benzo[b]furan-2-thiolates. On acidifying the thiolates benzo[b]furan-2-thiols were obtained. 4-(4-and -5-Benzyloxy-2-hydroxyphenyl)-1,2,3-thiadiazoles formed analogously the corresponding benzo[b]furan-2-thiolates whose acidifying afforded polymeric compounds.

The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors

A series of para-substituted phenolic N-alkyl carbamates were evaluated for their FAAH and MGL inhibitory activities. The compounds were generally selective for FAAH, with IC50 values in the nM range, whereas inhibition of MGL required concentrations three orders of magnitude higher. The most potent compounds, dodecylcarbamic acid 4-(4,5-dihydrothiazol-2-yl)phenyl (12) and 4-(1,2,3-thiadiazol-4-yl)phenyl (26) esters, inhibited FAAH and MGL with IC50 values at the low-nanomolar (IC50s; 0.0063 and 0.012 μM) and the low-micromolar ranges (IC50s; 2.1 and 1.0 μM), respectively. Compound 26 also inhibited both FAAH-dependent AEA uptake and AEA hydrolysis (IC50; 0.082 μM) by intact RBL2H3 cells, and could also reduce 2-AG hydrolysis by these cells at concentrations ≥0.030 μM.

4-(2-Hydroxyaryl)-1,2,3-thiadiazoles as a source of 2-benzofuranthiolates

Following the Hurd-Mori procedure, 4-(2-hydroxyaryl)-1,2,3-thiadiazoles were synthesized from o-hydroxyacetophenones. Treatment of the products with bases gives 2-benzofuranthiolates which can be involved in alkylation and arylation reactions.

Nucleophilic intramolecular cyclization reactions of alkynechalcogenolates

2-(ortho-Hydroxyphenyl)-alkynethiolates and -selenolates, obtained through base catalyzed ring cleavage of 4-(ortho-hydroxyphenyl)-1,2,3- thiadiazoles and -1,2,3-selenadiazoles, smoothly transform into 2- benzofuranthiolates and -selenolates. These reactive intermediates can be alkylated in high yield. This reaction sequence could be applied to the synthesis of electron rich thiacrown ethers. The 2-(ortho-aminophenyl)- alkynethiolate analogously forms 2-methylsulfanylindole. (C) 2000 Elsevier Science Ltd.

A general synthesis of benzofuran-2-thiolates via intramolecular addition of phenolates to alkynethiolates

4-(ortho-Hydroxyaryl)-1,2,3-thiadiazoles can be transformed into benzofuran-2-thiolates via an intramolecular cyclization.

BETA-ADRENERGIC BLOCKING AGENTS IN THE 1,2,3-THIADIAZOLE SERIES

Novel 4-2,3 or 4(3-amino-2-hydroxypropoxy) phenyl!-and 5-2, 3 or 4(3-amino-2-hydroxypropoxy) phenyl!-1,2,3-thiadiazole derivatives which may be further substituted at the C-5 or C-4 position of the thiadiazole ring, respectively, by a lower alkyl, phenyl, trifluoromethyl, carboxy, alkoxycarbonyl, cyano or an aminocarbonyl group, and the pharmaceutically acceptable acid addition salts thereof and processes for the production of such compounds; 4-4(3-t-butylamino-2-hydroxypropoxy) phenyl!-1,2,3-thiadiazole and 5-4(3-t-butylamino-2-hydroxypropoxy) phenyl!-1,2,3-thiadiazole are representative of the class. These compounds possess cardiovascular activity and are useful for the treatment of abnormal heart conditions in mammals.