61019-25-8

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
4-AMINO-5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL is used as a compound with potential biological activities for pharmaceutical research and drug development. Its anticancer, antimicrobial, and antifungal properties make it a promising candidate for the development of new therapeutic agents.
Used as a Building Block in the Synthesis of Bioactive Molecules:
In the field of medicinal chemistry, 4-AMINO-5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL is used as a building block in the synthesis of various bioactive molecules. Its unique structure and functional groups contribute to the creation of new compounds with potential therapeutic applications.
4-AMINO-5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL's potential for further exploration and development in medicinal chemistry highlights its importance in the discovery of novel treatments and pharmaceuticals.

InChI:InChI=1/C8H7FN4S/c9-6-3-1-5(2-4-6)7-11-12-8(14)13(7)10/h1-4H,10H2,(H,12,14)

Upstream product

• 736084-51-8 N'-(4-fluoro-benzoyl)-hydrazinecarbodithioic acid 
• 456-06-4 4-fluorobenzoyl hydrazide 
• 403-33-8 methyl 4-flurobenzoate 
• 456-22-4 4-Fluorobenzoic acid 
• 3926-62-3 sodium monochloroacetic acid 
• 90172-63-7 1-(p-fluorophenylcarbonyl)imidazole 
• 61019-29-2 C₈H₆FN₂OS₂^(1-)*K⁽¹⁺⁾ 
• 41421-13-0 2-mercapto-5-(4-fluorophenyl)-1,3,4-oxadiazole 
• 75-15-0 carbon disulfide 
• 451-46-7 4-fluorobenzoic acid ethyl ester 
• 403-43-0 4-fluorobenzoyl chloride 
• 41421-13-0 5-(4-fluorophenyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione 

Downstream Products

• 76457-84-6 3-(4-Fluorophenyl)-8-Phenyl-1,2,4-triazolo<3,4-b>-1,3,4-thiadiazepine 
• 724432-38-6 3-(4-fluorophenyl)-6-phenethyl[1,2,4]triazolo[3,4-b][1,3,4] thiadiazole 
• 573950-93-3 4-(4-nitrobenzylideneamino)-5-(4-fluorophenyl)-4H-1,2,4-triazole-3-thiol 
• 585555-78-8 2-(3-(4-fluorophenyl)-5-mercapto-4H-1,2,4-triazol-4-ylimino) phenol 
• 791824-26-5 3-(4-fluorophenyl)-6-(phenoxymethyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 825606-03-9 6-((4-chlorophenoxy)methyl)-3-(4-fluorophenyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 825606-04-0 3-(4-fluorophenyl)-6-((4-methoxyphenoxy)methyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 

Relevant academic research and scientific papers

Insights into the nature of weak noncovalent interactions in 3-(4-fluorophenyl)-6-(2-fluorophenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole, a potential bioactive agent: X-ray, QTAIM and molecular docking analysis

A thorough examination of weak interactions present in the crystal structure of the title compound was investigated. Intramolecular C–H?N and F?S interactions make the molecule as fused 6,5,5,5,6,6-membered ring system. Two of the closely related structur

Development of triazolothiadiazine derivatives as highly potent tubulin polymerization inhibitors: Structure-activity relationship, in vitro and in vivo study

Based on our prior work, we reported the design, synthesis, and biological evaluation of fifty-two new triazolothiadiazine-based analogues of CA-4 and their preliminary structure-activity relationship. Among synthesized compounds, Iab was found to be the most potent derivative possessing IC50 values ranging from single-to double-digit nanomolar in vitro, and also exhibited excellent selectivity over the normal human embryonic kidney HEK-293 cells (IC50 > 100 μM). Further mechanistic studies revealed that Iab significantly blocked tubulin polymerization and disrupted the intracellular microtubule network of A549 cells. Moreover, Iab induced G2/M cell cycle arrest by regulation of p-cdc2 and cyclin B1 expressions, and caused cell apoptosis through up-regulating cleaved PARP and cleaved caspase-3 expressions, and down-regulating of Bcl-2. Importantly, in vivo, Iab effectively suppressed tumor growth of A549 lung cancers in a xenograft mouse model without obvious signs of toxicity, confirming its potential as a promising candidate for cancer treatment.

Synthesis and antitumor evaluation of novel fused heterocyclic 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole derivatives

In this study, twenty three 3,6-disubstituted 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole derivatives were synthesized and their antiproliferative activities in vitro were studied against SMMC-7721, HeLa, A549, and L929 by the CCK-8 assay. The bioassay results demonstrated that all tested compounds 8(a–w) exhibited antiproliferation with different degrees, and some compounds showed better effects than reference drug 5-fluorouracil. Among these screened compounds, compounds 8a, 8d, and 8l displayed significant antitumor activities in inhibiting SMMC-7721cell proliferation with IC50 values of 1.64, 1.74, and 1.61 μM, respectively. Compounds 8d and 8l were manifested highly effective biological activity versus HeLa cells with IC50 values of 2.23 and 2.84 μM, respectively. Compound 8l was found to have the highest antitumor potency against A549 cells with IC50 value of 2.67 μM. Furthermore, all compounds exhibited weaker cytotoxic effects than 5-fluorouracil on normal cell lines L929.

Design, Synthesis and Evaluation of Antitubercular Activity of Novel 1,2,4-Triazoles Against MDR Strain of Mycobacterium tuberculosis

Emergence of various forms of resistant strains of Mycobacterium tuberculosis led to the exploration of drugs with novel mechanism of action. Recently econazole, an azole based antitubercular agent, attracted major attention for targeting mycobacterial cytochrome P450. In the present study, we designed novel 1,2,4-triazole derivatives based on econazole moiety and evaluated them for in vitro antitubercular activity against M. tuberculosis H37Rv and multi-drug resistant (MDR) strains of Mycobacterium.

Synthesis and biological activities of cyclanone O-(2-(3-aryl-4- amino-4H-1,2,4-triazol-3-yl)thio)acetyl)oxime derivatives

Twelve cyclanone O-(2-(3-aryl-4-amino-4H-1,2,4-triazol-3-yl)thio)acetyl)oxime derivatives were synthesized and their structures were confirmed by spectroscopy (IR, 1H NMR, 13C NMR, 19F NMR) and elemental analysis. Their antifungal and antibacterial activities were evaluated against six fungi (Gibberella zeae, Fusarium oxysporum, Clematis mandshurica, Phytophthora infestans, Paralepetopsis sasakii, Sclerotinia sclerotiorum) and two bacteria (Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas citri subsp. Citri (Xcc)). The results indicated that most of the title compounds exhibited good antibacterial activities. Among them, compounds 6d, 6g, 6h, and 6j showed better antibacterial activities against Xoo and Xcc than that of the commercial agent thiodiazole-copper.

Synthesis and biological activities of 3,6-disubstituted-1,2,4-triazolo-1,3,4-thiadiazole derivatives

Twelve novel triazolothiadiazole derivatives were synthesized from 4-amino-5-substituted-4H-1,2,4-triazole-3-thiols with various aromatic carboxylic acids by cyclization in the presence of phosphorous oxychloride. All the newly synthesized compounds were characterized by FTIR, 1H NMR, mass spectroscopy and elemental analysis. The antimicrobial activities of the title compounds were examined by disc diffusion method against Escherichia coli, Staphylococcus aureus, Pyricularia oryzae and Rhizoctnia solani. The bioassay indicated all synthesized triazolothiadiazole derivatives possessed moderate to good antibacterial and antifungal activities against the tested organisms. Especially, compounds 2e and 2k exhibited excellent antibacterial and antifungal activities among these triazolothiadiazole derivatives.

1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole compound and application thereof

The invention discloses a group of 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole compounds, and application thereof, namely application of ten 3-substituted phenyl-6-butyl dithio-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole compounds comprising 3-phenyl-6-n-butyl dithio-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole, 3-phenyl-6-isobutyl dithio-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole, 3-p-methoxyphenyl-6-n-butyl dithio-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole and the like. The ten compounds have antitumor activity, are used for preparing drugs for fighting against cervical cancer (Hela), liver cancer (SMMC-7721) and lung cancer (A549), and create a new way for developing a new cancer-fighting drug.

Synthesis and antibacterial activity of oxime ester derivatives containing 1,2,4-triazole or 1,3,4-oxadiazole moiety

A series of oxime ester derivatives containing 1,2,4-triazole or 1,3,4-oxadiazole moiety were designed and synthesized, and their antibacterial activities in vitro against Xanthomonas axonopodis pv. citri (Xac) and Xanthomonas oryzae pv. oryzae (Xoo) were

SAR studies on 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles as inhibitors of Mtb shikimate dehydrogenase for the development of novel antitubercular agents

Shikimate dehydrogenase, an essential protein for the biosynthesis of the chorismate end product, is a highly promising therapeutic target, especially for the discovery and development of new-generation anti-TB agents. Following up the identification of one lead 3,6-disubstituted 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole (1), targeting Mt SD in our previous study, an extensive SAR study for optimization of the lead compound was performed through systematic modification of the 3 and 6 positions. This study has successfully led to the discovery of two highly potent advanced leads 6d-4, 6c-4 and several other compounds with comparable potencies (6d-4, MIC-H37Rv = 0.5 μg mL-1; MIC-MDRTB = 4.0 μg mL-1; MIC-RDRTB = 0.5 μg mL-1; Mt SD-IC50 = 14.20 μg mL-1; and 6c-4, MIC-H37Rv = 0.5 μg mL-1; MIC-MDRTB = 4.0 μg mL-1; MIC-RDRTB = 1.0 μg mL-1; Mt SD-IC50 = 6.82 μg mL-1). These advanced lead compounds possess a para-halogen phenyl at the 3 position. In vitro Mt SD inhibitory assay indicates that Mt SD is the target for their antitubercular activity. Moreover, the BacT/ALERT 3D liquid culture technology and in vitro Mt SD inhibitory assay were initially applied.