69480-15-5

Usage

Uses

Used in Industrial Processes:
5-[4-(tert-Butyl)phenyl]-1H-1,2,4-triazole-3-thiol is used as a corrosion inhibitor for protecting metal surfaces from degradation in various industrial applications. Its effectiveness in inhibiting corrosion makes it a valuable additive in the production of metal coatings and treatments, ensuring the longevity and integrity of metal structures.
Used in Agriculture:
In the agricultural sector, 5-[4-(tert-Butyl)phenyl]-1H-1,2,4-triazole-3-thiol is utilized as a fungicide and pesticide. It has demonstrated its ability to inhibit the growth of a broad spectrum of fungi and bacteria, thereby protecting crops from diseases and pests. This contributes to increased crop yields and reduced losses due to infections.
Used in Pharmaceutical Research:
5-[4-(tert-Butyl)phenyl]-1H-1,2,4-triazole-3-thiol also exhibits potential pharmaceutical properties, sparking interest in its possible use as a therapeutic agent for various medical conditions. Ongoing research aims to explore its potential benefits and applications in the medical field, which could lead to the development of new treatments and therapies.

InChI:InChI=1/C12H15N3S/c1-12(2,3)9-6-4-8(5-7-9)10-13-11(16)15-14-10/h4-7H,1-3H3,(H2,13,14,15,16)

Upstream product

• 43100-38-5 4-tert-butylbenzoic acid hydrazide 
• 1147550-11-5 ammonium thiocyanate 
• 26537-19-9 methyl 4-tert-butylbenzoate 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 1001510-99-1 4-benzyl-3-(4-tert-butylphenyl)-5-(phenylsulfanyl)-4H-1,2,4-triazole 

Downstream Products

• 261622-94-0 5-(p-chlorobenzoyl)methylmercapto-3-[p-(t-butylphenyl)]-s-triazole 
• 1121614-93-4 6-(4-tert-butylphenyl)-1,1-dioxo-3-pyrrolidino-1λ⁶-[1,2,4]triazolo[2,3-b][1,4,2,6]dithiadiazine 
• 1121614-96-7 6-(4-tert-butylphenyl)-1,1-dioxo-3-piperidino-1λ⁶-[1,2,4]triazolo[2,3-b][1,4,2,6]dithiadiazine 
• 1121614-87-6 6-(4-tert-butylphenyl)-3-dimethylamino-1,1-dioxo-1λ⁶-[1,2,4]triazolo[2,3-b][1,4,2,6]dithiadiazine 
• 1620200-71-6 diethyl (3-((5-(4-(tert-butyl)phenyl)-1H-1,2,4-triazol-3-yl)thio)propyl)phosphonate 

Relevant academic research and scientific papers

Discovery of [1,2,4]triazole derivatives as new metallo-β-lactamase inhibitors

The emergence and spread of metallo-β-lactamase (MBL)-mediated resistance to β-lactam antibacterials has already threatened the global public health. A clinically useful MBL inhibitor that can reverse β-lactam resistance has not been established yet. We here report a series of [1,2,4]triazole derivatives and analogs, which displayed inhibition to the clinically relevant subclass B1 (Verona integron-encoded MBL-2) VIM-2. 3-(4-Bromophenyl)-6,7-dihydro-5H-[1,2,4]triazolo [3,4-b][1,3]thiazine (5l) manifested the most potent inhibition with an IC50 (half-maximal inhibitory concentration) value of 38.36 μM. Investigations of 5l against other B1 MBLs and the serine β-lactamases (SBLs) revealed the selectivity to VIM-2. Molecular docking analyses suggested that 5l bound to the VIM-2 active site via the triazole involving zinc coordination and made hydrophobic interactions with the residues Phe61 and Tyr67 on the flexible L1 loop. This work provided new triazole-based MBL inhibitors and may aid efforts to develop new types of inhibitors combating MBL-mediated resistance.

An efficient nonconventional glycerol-based solid acid catalyzed synthesis and biological evaluation of phosphonate conjugates of 1,2,4-triazole thiones

A series of diethyl (3-((5-aryl-1H-1,2,4-triazol-3-yl)thio)propyl)phos-phonates (7a-t) has been synthesized in excellent yields by coupling diethyl (3-bromopropyl)phosphonate and 5-aryl-1H- 1,2,4-triazol-3-thiones employing an efficient, green and nonconventional heterogeneous SO3Hcarbon catalyst derived from glycerol. In addition, a facile and green approach for the esterification of carboxylic acids by utilizing glycerol-based solid acid catalyst has been reported. Structures of the synthesized compounds were characterized by IR, NMR and HRMS studies. These triazole derivatives were screened for their in vitro cytotoxicity using the standard MTT (3-(4,5-dimethylthiazol-2- yl)-2,5-diphenyltetra-zolium bromide) assay against a panel of five different human cancer cell lines (HeLa: Cervix, A549: Lung, A375: Skin, MDA-MB-231: Breast and T98G: Brain). The antimicrobial activities of the synthesized compounds were investigated against four bacterial strains: Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and three fungal strains: Aspergillus Niger, Aspergillus terreus, Aspergillus fumigatus. Preliminary results indicate that the compound 7f displayed maximum anticancer activity and the compounds 7d, 7e, 7f, 7m and 7q exhibited moderate antibacterial activity. The compounds 7g, 7h, 7o and 7p showed good antifungal activity with high inhibition zone diameter compared to the standard drug.

Magnetically Recyclable Nano-Fe 2O 3-Catalyzed Chemoselective Synthesis and Antioxidant Activity of Diethyl (3-((5-Aryl-1 H-1,2,4-triazol-3-yl)thio)propyl) phosphonates

An efficient, green, and chemoselective S-alkylation of 5-aryl-1H-1,2,4-triazole-3-thiones with diethyl (3-bromopropyl)phosphonate in water, catalyzed by nano-Fe2O3 under ligand-and base-free conditions, is reported. Clean reaction, less expensive catalyst, excellent yields, and easy workup are the advantages of the present method. The catalyst can be easily collected by a magnet and recycled without significant loss in catalytic activity. The newly synthesized compounds were screened for their antioxidant property by using 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging assay. The majority of the compounds exhibited good antioxidant activity.

Synthesis of 5-substituted 3-mercapto-1,2,4-triazoles via Suzuki-Miyaura reaction

3-Bromo- and 3-iodo-N,S-dibenzyl-5-mercapto-1,2,4-triazoles were prepared and demonstrated as versatile building blocks for Suzuki-Miyaura cross-coupling with aryl, heteroaryl, and vinyl boronic acid derivatives. Deprotection of the resulting coupling products provided 5-substituted-3-mercapto-1,2,4-triazoles in good overall yields. This represents a novel and convenient approach for the introduction of a 3-mercapto-1,2,4-triazole substructure into target compounds.

Synthesis of new S-alkylated-3-mercapto-1,2,4-triazole derivatives bearing cyclic amine moiety as potent anticancer agents

A series of 3-[3-[4-(Substituted)-1-cyclicamine]propyl]thio-5- substituted[1,2,4]triazoles (8a-j) were synthesized with good yields starting from corresponding carboxylic acids. The cytotoxicity studies of these derivatives were studied against five different human cancer cell lines. Three compounds had shown good anticancer activity. The triazole derivatives, 8i and 8j were most potent particularly against U937 and HL-60 cells. The cytotoxic potency of the compounds varied between the cell lines suggesting that a structural property of these compounds as possible determinants of their biological activity.

N,N-dialkyl-N′-chlorosulfonyl chloroformamidines in heterocyclic synthesis. VI the preparation of some fused [1,4,2,6]dithiadiazine dioxides

N,N-Dialkyl-N′-chlorosulfonylchloroformamidines 1 were treated with 2-mercaptobenzimidazoles 2 to give [1,4,2,6]dithiadiazino[2,3-a]benzimidazole 1,1-dioxides 3. 3-Mercapto[1,2,4]triazoles 5 afforded [1,2,4]triazolo[2,3-b][1, 4,2,6]dithiadiazine 1,1-dioxides 6 and [1,2,4]triazolo[4,3-b][1,4,2,6] dithiadiazine 1,1-dioxides 7. These products are derivatives of new or very rare heterocycles. CSIRO 2008.

Heterocyclic systems containing bridgehead nitrogen atom: Synthesis and bioactivity of thiazolo[3, 2-b]-s-triazoles and isomeric thiazolo[2, 3-c]-s-triazoles

The reaction of 3-[p-(t-butyl phenyl)]-5-mereapto-s-triazole 2 with α-haloketones gives, in two steps, 5-substituted-2-[p-(t-butyl phenyl)] thiazolo[3, 2-b]-s-triazoles 4 and not the isomeric 5-substituted-3-[p-(t-butyl phenyl)] thiazolo[2, 3-c]-striazole