114058-91-2

Basic information

• Product Name: 5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL
• Synonyms: CHEMBRDG-BB 4012401;5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL;4H-1,2,4-triazole-3-thiol, 5-(4-fluorophenyl)-;5-(4-fluorophenyl)-4H-1,2,4-triazole-3-thiol(SALTDATA: FREE);2,4-Dihydro-5-(4-fluorophenyl)-3H-1,2,4-triazole-3-thione;3H-1,2,4-Triazole-3-thione, 2,4-dihydro-5-(4-fluorophenyl)-;5-(4-fluorophenyl)-1,2-dihydro-1,2,4-triazole-3-thione;3H-1,2,4-Triazole-3-thione, 5-(4-fluorophenyl)-1,2-dihydro-
• CAS NO: 114058-91-2
• Molecular Formula: C₈H₆FN₃S
• Molecular Weight: 195.22
• Mol File: 114058-91-2.mol

Chemical Properties

• Boiling Point: 263.2°Cat760mmHg
• Flash Point: 113°C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 0.0104mmHg at 25°C
• Refractive Index: 1.707
• CAS DataBase Reference: 5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL(114058-91-2)
• EPA Substance Registry System: 5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL(114058-91-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 114058-91-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL is utilized as a key building block in the development of pharmaceuticals. Its unique structure allows for the creation of new drugs with specific therapeutic properties, making it a valuable component in medicinal chemistry.
Used in Agrochemical Development:
In the agrochemical industry, 5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL is employed as a fundamental component in the synthesis of various agrochemicals. Its incorporation can lead to the development of novel compounds with enhanced pesticidal or herbicidal activities, contributing to more effective crop protection strategies.
Used in Cancer Research:
5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL is studied for its potential anti-cancer activities. Its specific molecular features may contribute to the inhibition of cancer cell growth or the disruption of cancer-related pathways, offering a promising avenue for the discovery of new cancer therapeutics.
Used in Antibacterial Research:
5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL is also being investigated for its anti-bacterial properties. Given the increasing prevalence of antibiotic resistance, 5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL may provide a new approach to combating bacterial infections, potentially leading to the development of new antibiotics.
Used in Chemical Research:
5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL serves as a subject of interest in chemical research, where its unique properties are explored for potential applications in various chemical processes and reactions, broadening its utility beyond the pharmaceutical and agrochemical realms.

InChI:InChI=1/C8H6FN3S/c9-6-3-1-5(2-4-6)7-10-8(13)12-11-7/h1-4H,(H2,10,11,12,13)

Upstream product

• 831-38-9 2-(4-fluorobenzoyl)hydrazinecarbothioamide 
• 456-06-4 4-fluorobenzoyl hydrazide 
• 2714-90-1 phenyl 4-fluorobenzoate 
• 403-43-0 4-fluorobenzoyl chloride 
• 456-22-4 4-Fluorobenzoic acid 
• 403-33-8 methyl 4-flurobenzoate 
• 79-19-6 thiosemicarbazide 

Downstream Products

• 116850-62-5 3-(4-Fluoro-phenyl)-5-methylsulfanyl-4H-[1,2,4]triazole 
• 1363773-47-0 3-(4-benzylpiperazino)propyl [5-(4-fluorophenyl)-4H-1,2,4-triazol-3-yl]sulfide 
• 1456543-23-9 1-[3-(4-benzylpiperazino)propyl]-3-(4-fluorophenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione 

Relevant articles and documents

Novel panaxadiol triazole derivatives induce apoptosis in HepG-2 cells through the mitochondrial pathway

In this study, we introduced 1, 2, 4-triazole groups into panaxadiol (PD) to obtain 18 panaxadiol triazole derivatives. Five cancer cells and one normal cell were evaluated for cytotoxicity by MTT assay. The results showed that most of the derivatives could inhibit cancer cell proliferation, and the anti-proliferative activity of compound A1 was the most significant. For HepG-2 cells, the IC50 value was 4.21 ± 0.54 μM, which was nearly 15 times higher than the activity of PD. Further studies showed that compound A1 could induce apoptosis in HepG-2 cells, and could enhance the expression of Cl-caspase-3, Cl-caspase-9 and Cl-PARP. Moreover, Western blot analysis showed that after treating HepG-2 cells with compound A1, the expression of p53 protein was increased and the ratio of Bax/Bcl-2 was gradually increased. The cytoplasmic Bax is then translocated to the mitochondria, causing the release of Cyt c protein. Therefore, the results indicate that compound A1 induces apoptosis through the mitochondrial pathway and can be used the potential to develop new anti-proliferative agents.

Dammarane sapogenin derivative and preparation method and application thereof

The invention belongs to the technical field of medicines, and relates to a dammarane sapogenin derivative and a preparation method and application thereof. A series of dammarane sapogenin derivativesare obtained by combining dammarane sapogenins from plants with different groups. Anticancer activity evaluation and anticancer activity mechanism research are carried out on the derivative, and results show that the prepared dammarane sapogenin derivative has a remarkable anticancer effect, has no toxic effect on normal cells and can be used for preparing drugs for treating cancers.

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.

5H - [1, 2, 4] triazole [5, 1 - b] [1, 3] thiazine derivative and application thereof

The invention discloses a 5H-[1, 2, 4] triazole [5, 1-b] [1, 3] thiazide derivative with a general formula I, or a pharmaceutically acceptable aquo-complex and salts of the derivative; the derivative comprises a stereisomer or a tautomer, wherein R1 and R2 in the formula I are respectively independent hydrogen, methyl, halogen, hydroxyl, methoxyl, acetyl, propiono, nitro or alkoxy. The 5H-[1, 2, 4] triazole [5, 1-b] [1, 3] thiazide derivative has an obvious inhibiting effect on acetylcholin esterase, and is used for improving the memory of a patient suffering from dementia and Alzheimer's disease. The invention also relates to a preparation method of the compound and an application in preparation of a drug for treating Senile Dementia.

Click 1,4-regioselective synthesis, characterization, and antimicrobial screening of novel 1,2,3-triazoles tethering fluorinated 1,2,4-triazole and lipophilic side chain

Base-catalyzed alkylation of 5-(4-fluorophenyl)-2,4-dihydro-1,2,4-triazole-3-thione (3) with one or two equivalents of propargyl bromide in presence of triethylamine as catalyst selectively produced the thiopropargylated 1,2,4-triazole 7 in 90?% yield. Un

Synthesis and biological evaluation of 1,2,4-triazole-3-thione and 1,3,4-oxadiazole-2-thione as antimycobacterial agents

Resistance among dormant mycobacteria leading to multidrug-resistant and extremely drug-resistant tuberculosis is one of the major threats. Hence, a series of 1,2,4-triazole-3-thione and 1,3,4-oxadiazole-2-thione derivatives (4a–5c) have been synthesized and screened for their antitubercular activity against Mycobacterium tuberculosis H37Ra (H37Ra). The triazolethiones 4b and 4v showed high antitubercular activity (both MIC and IC50) against the dormant H37Ra by in vitro and ex vivo. They were shown to have more specificity toward mycobacteria than other Gram-negative and Gram-positive pathogenic bacteria. The cytotoxicity was almost insignificant up to 100?μg/ml against THP-1, A549, and PANC-1 human cancer cell lines, and solubility was high in aqueous solution, indicating the potential of developing these compounds further as novel therapeutics against tuberculosis infection.

1,2,4-TRIAZOLE, 1,3,4-OXADIAZOLE, AND 1,3,4-THIADIAZOLE DERIVATIVES AND THEIR ANTIMYCOBACTERIAL ACTIVITY

Disclosed herein are novel five membered heterocyclic compounds of Formula (I) wherein, X is S or SO2; n is 0, 1; m is1 or 2; Y is N, O or S; R2 independently represents H or alkyl or halo selected from -CI, -F; or -CF3, or -OH or-NH2 or - NO2; and R1 independently represents H or C1 to C5 straight or branched chain alkyl, alkenyl, alkynyl or a group -(CH2)5Br or pyrrolidine or - NHR' wherein R' is H or isopropyl or (II) or (III) which selectively act against dormant pathogenic tuberculi bacilli and exhibit antiproliferative activities and for treatment of a disease or disorder associated with GroEL1/GroEL2 activity. The invention relates to a process for preparation of novel five membered heterocyclic compounds of Formula I and to pharmaceutical compositions thereof.

Synthesis, characterization, and anticancer studies of S and N alkyl piperazine-substituted positional isomers of 1,2,4-triazole derivatives

A series of 3-[3-[4-(substituted)-1-cyclicamine] propyl]thio-5- substituted[1,2,4]triazoles (8a-m) and 2-[3-[4-(substituted)-1-cyclicamine] propyl]-5-(substituted)-2,4-dihydro-3H[1,2,4]triazole-3-thiones (9a-h) were synthesized with good yields starting from corresponding carboxylic acids using two different methods. The cytotoxicity studies of these derivatives were studied against five different human cancer cell lines. Six compounds had shown good anticancer activity. The triazole derivatives, 9d, 8j, and 8i 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 determinant of their biological activity. Springer Science+Business Media 2013.

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.

THIAZOLTRIAZOLES AND THIAZOLIMIDAZOLES AS ANTAGONISTS OF THE MGLUR5 RECEPTOR

This invention relates to novel thiazolotriazole and thiazoloimidazole derivatives of formula (I). The invention also relates to the use of the derivatives in treating diseases and conditions wherein antagonism of the mGluR5 receptor is beneficial, in particular substance related disorders. In addition, the invention relates to compositions containing the derivatives and processes for their preparation.