93677-89-5

Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-5-(2,4-DICHLORO-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL is used as an intermediate in the synthesis of various medications, particularly those targeting microbial infections. Its potential antibacterial and antifungal properties make it a valuable component in the development of new drugs to combat resistant strains of bacteria and fungi.
Used in Materials Science:
In the field of materials science, 4-AMINO-5-(2,4-DICHLORO-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL serves as a building block for the production of various organic compounds and materials. Its unique chemical structure allows it to be incorporated into a wide range of applications, from polymers to coatings, offering new possibilities for material development and innovation.

InChI:InChI=1/C8H6Cl2N4S/c9-4-1-2-5(6(10)3-4)7-12-13-8(15)14(7)11/h1-3H,11H2,(H,13,15)

Upstream product

• 23288-92-8 2-mercapto-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole 
• 5814-06-2 2,4-dichlorobenzohydrazide 
• 56882-52-1 ethyl 2,4-dichlorobenzoate 
• 75-15-0 carbon disulfide 
• 50-84-0 2,4 dichlorobenzoic acid 
• 2231-57-4 Thiocarbohydrazide 
• 35112-28-8 methyl 2,4-dichlorobenzoate 

Downstream Products

• 135220-22-3 6-(2,4-Dichloro-phenyl)-2-methoxy-[1,2,4]triazolo[4,3-d][1,3,4,2]thiadiazaphosphole 2-sulfide 
• 135220-19-8 6-(2,4-Dichloro-phenyl)-2-isopropoxy-[1,2,4]triazolo[4,3-d][1,3,4,2]thiadiazaphosphole 2-oxide 
• 135220-18-7 6-(2,4-Dichloro-phenyl)-2-propoxy-[1,2,4]triazolo[4,3-d][1,3,4,2]thiadiazaphosphole 2-oxide 
• 135220-24-5 6-(2,4-Dichloro-phenyl)-2-isopropoxy-[1,2,4]triazolo[4,3-d][1,3,4,2]thiadiazaphosphole 2-sulfide 
• 135220-23-4 6-(2,4-Dichloro-phenyl)-2-propoxy-[1,2,4]triazolo[4,3-d][1,3,4,2]thiadiazaphosphole 2-sulfide 
• 135220-20-1 2-Butoxy-6-(2,4-dichloro-phenyl)-[1,2,4]triazolo[4,3-d][1,3,4,2]thiadiazaphosphole 2-oxide 
• 135220-25-6 2-Butoxy-6-(2,4-dichloro-phenyl)-[1,2,4]triazolo[4,3-d][1,3,4,2]thiadiazaphosphole 2-sulfide 
• 135220-26-7 6-(2,4-Dichloro-phenyl)-2-pentyloxy-[1,2,4]triazolo[4,3-d][1,3,4,2]thiadiazaphosphole 2-sulfide 
• 128032-41-7 3,6-Bis-(2,4-dichloro-phenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 128032-44-0 4-[3-(2,4-Dichloro-phenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl]-benzene-1,3-diol 
• 133527-90-9 3-(2,4-dichlorophenyl)-6,7-difuryl-5H-s-triazolo<3,4-b><1,3,4>thiadizine 
• 128032-51-9 6-(4-Chloro-phenyl)-3-(2,4-dichloro-phenyl)-5,6-dihydro-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 139081-29-1 Benzyl-[3-(2,4-dichloro-phenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl]-amine 
• 133527-89-6 3-(2,4-dichlorophenyl)-6,7-diphenyl-5H-s-triazolo<3,4-b><1,3,4>thiadizine 

Relevant academic research and scientific papers

Rational Optimization and Action Mechanism of Novel Imidazole (or Imidazolium)-Labeled 1,3,4-Oxadiazole Thioethers as Promising Antibacterial Agents against Plant Bacterial Diseases

The emergence and widespread occurrence of plant bacterial diseases that cause global production constraints have become major challenges to agriculture worldwide. To promote the discovery and development of new bactericides, imidazole-labeled 1,3,4-oxadiazole thioethers were first fabricated by integrating the crucially bioactive scaffolds of the imidazole motif and 1,3,4-oxadiazole skeleton in a single molecular architecture. Subsequently, a superior antibacterial compound A6 was gradually discovered possessing excellent competence against plant pathogens Xanthomonas oryzae pv oryzae and Xanthomonas axonopodis pv citri with EC50 values of 0.734 and 1.79 μg/mL, respectively. These values were better than those of commercial agents bismerthiazol (92.6 μg/mL) and thiodiazole copper (77.0 μg/mL). Further modifying the imidazole moiety into the imidazolium scaffold led to the discovery of an array of potent antibacterial compounds providing the corresponding minimum EC50 values of 0.295 and 0.607 μg/mL against the two strains. Moreover, a plausible action mechanism for attacking pathogens was proposed based on the concentration dependence of scanning electron microscopy, transmission electron microscopy, and fluorescence microscopy images. Given the simple molecular structures, easy synthetic procedure, and highly efficient bioactivity, imidazole (or imidazolium)-labeled 1,3,4-oxadiazole thioethers can be further explored and developed as promising indicators for the development of commercial drugs.

A process for preparing 3 - substituted - 6 - ferrocenyl methylene - 1, 2, 4 - triazolo [3.4 - b] - 1, 3, 4 - thiadiazole method

The invention relates to a method for preparing 3-substituted-6-ferrocenylmethylene-1,2,4-triazolo[3.4-b]-1,3,4-thiadiazole. The method comprises the following steps: 1) adding A mmol of ferrocenyl acetic acid, B mmol of 3-substituted-4-amino-5-sulfhydryl

Polyethylene glycol mediated, one-pot, three-component synthetic protocol for novel 3-[3-substituted-5-mercapto-1,2,4-triazol-4-yl]-spiro-(indan-1′,2-thiazolidin)-4-ones as new class of potential antimicrobial and antitubercular agents

A series of 3-[3-substituted-5-mercapto-1,2,4-triazol-4-yl]-spiro-(indan-1′,2-thiazolidin)-4-ones 2 were designed for the purpose of searching for novel antimicrobial agents and have been synthesized conveniently in a single step with a three-component protocol in polyethylene (400) as green reaction media. Thus, the condensation reaction between indane-1-one; 4-amino-5-mercapto-1,2,4-triazoles and mercaptoacetic acid in polyethylene glycol (400) gave quantitatively and analytically pure titled compounds 2. The structure of synthesized compound 2 is based on spectral (IR, 1H-NMR, and 13C-NMR) as well elemental analyses. These compounds have been screened for their antibacterial, antifungal, and antitubercular activities. Some of them have showed significant inhibition on fungal and bacterial growth and antitubercular activity against Mycobacterium tuberculosis. The compounds 2a, 2d, and 2e display antifungal activity against Candida albicans [minimum inhibitory concentration (MIC) 3.13, 6.25 μg/mL] and antibacterial activity against Streptococcus pneumoniae (MIC 3.13 μg/mL) of the order of standard drugs tested under similar conditions, and compound 2a showed better antitubercular activity than other compounds against M. tuberculosis (H37Rv strain, MIC 12.5 μg/mL).

Novel lead structures for p38 MAP kinase via FieldScreen virtual screening

p38 MAP kinase has received considerable interest in the pharmaceutical industry and remains a valid and interesting target for the treatment of inflammation. To discover novel p38 inhibitors, we applied the ligand-based virtual screening technique, FieldScreen, to 1.2 million commercially available compounds. Fifty-eight diverse compounds were selected for biological analysis, using molecular field similarity to known inhibitors, while explicitly removing any structure that shared a scaffold with previously reported p38 inhibitors. Of these, 11 (19%) showed ≥20% inhibition of p38 at 10 μM. We chose to prepare analogues of two distinct chemical series resulting in a potential lead compound with pIC50 of 6.4. Modeling of SAR using FieldAlign, a ligand alignment protocol, was used to rationalize the SAR of the series of thiadiazole based inhibitors.

Synthesis and antifungal activity of some 3-aryl-8-nitro-1,2,4-triazolobenzothiadiazepines

A number of 3-aryl-8-nitro-1,2,4-triazolobenzothiadiazepines (3) have been synthesized by cyclisation of 4-(2-chloro-5-nitrobenzylideneamino)-5-aryl-3-mercapto-1,2,4-triazoles (2) in pyridine.Their antifungal activity has been screened against Aspergillus niger and Helminthosporium oryzae and compared with that of commercial fungicide Carbendazim tested under similar conditions.