831-38-9

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-Fluorobenzoyl)hydrazinecarbothioamide is used as an intermediate in the synthesis of various pharmaceuticals for its potential role in creating new drug formulations.
Used in Agrochemical Industry:
2-(4-Fluorobenzoyl)hydrazinecarbothioaMide also serves as an intermediate in the synthesis of agrochemicals, contributing to the development of new pesticides or other agricultural products.
Used in Cancer Treatment Research:
2-(4-Fluorobenzoyl)hydrazinecarbothioamide is used as a potential therapeutic agent in cancer treatment due to its demonstrated cytotoxic and anti-proliferative activities against cancer cells.
Used in Material Science and Polymer Development:
Owing to its unique chemical structure and reactivity, 2-(4-Fluorobenzoyl)hydrazinecarbothioamide may be utilized in the development of new materials and polymers, expanding its applications in various industries.

Upstream product

• 456-06-4 4-fluorobenzoyl hydrazide 
• 333-20-0 potassium thioacyanate 
• 403-33-8 methyl 4-flurobenzoate 
• 79-19-6 thiosemicarbazide 
• 456-22-4 4-Fluorobenzoic acid 
• 403-43-0 4-fluorobenzoyl chloride 
• 2714-90-1 phenyl 4-fluorobenzoate 

Downstream Products

• 114058-91-2 5-(4-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 114058-91-2 3-(4-Fluoro)phenyl-5-mercapto-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 
• 1620200-74-9 diethyl (3-((5-(4-fluorophenyl)-1H-1,2,4-triazol-3-yl)thio)propyl)phosphonate 
• 23233-37-6 KUC₀₆₀₁₁₄ 

Relevant academic research and scientific papers

Synthesis and preliminary anticancer activity assessment of n-glycosides of 2-amino-1,3,4-thiadiazoles

The addition of 2-amino-1,3,4-thiadiazole derivatives with parallel iodination of differ-ently protected glycals has been achieved using a double molar excess of molecular iodine under mild conditions. The corresponding thiadiazole derivatives of N-glycosides were obtained in good yields and anomeric selectivity. The usage of iodine as a catalyst makes this method easy, inexpen-sive, and successfully useable in reactions with sugars. Thiadiazole derivatives were tested in a panel of three tumor cell lines, MCF-7, HCT116, and HeLa. These compounds initiated biological response in investigated tumor models in a different rate. The MCF-7 is resistant to the tested com-pounds, and the cytometry assay indicated low increase in cell numbers in the sub-G1 phase. The most sensitive are HCT-116 and HeLa cells. The thiadiazole derivatives have a pro-apoptotic effect on HCT-116 cells. In the case of the HeLa cells, an increase in the number of cells in the sub-G1-phase and the induction of apoptosis was observed.

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.

Design and development of 1,3,5-triazine-thiadiazole hybrids as potent adenosine A2A receptor (A2AR) antagonist for benefit in Parkinson's disease

Various studies showed adenosine A2A receptors (A2ARs) antagonists have profound therapeutic efficacy in Parkinsons Disease (PD) by improving dopamine transmission, thus being active in reversing motor deficits and extrapyramidal symptoms related to the disease. Therefore, in the presents study, we have showed the development of novel 1,3,5-triazine-thiadiazole derivative as potent A2ARs antagonist. In the radioligand binding assay, these molecules showed excellent binding affinity with A2AR compared to A1R, with significant selectivity. Results suggest, compound 7e as most potent antagonist of A2AR among the tested series. In docking analysis with A2AR protein model, compound 7e found to be deeply buried into the cavity of receptor lined via making numerous interatomic contacts with His264, Tyr271, His278, Glu169, Ala63, Val84, Ile274, Met270, Phe169. Collectively, our study demonstrated 1,3,5-triazine-thiadiazole hybrid as a highly effective scaffold for the design of new A2A antagonists.

Design and synthesis of 2,6-di(substituted phenyl)thiazolo[3,2-b]-1,2,4-triazoles as α-glucosidase and α-amylase inhibitors, co-relative Pharmacokinetics and 3D QSAR and risk analysis

Ten fused heterocyclic derivatives bearing the 2,6-di(subsituted phenyl)thiazolo[3,2-b]-1,2,4-triazoles as central rings were synthesized and structures of the compounds were established by analytical and spectral data using FTIR, EI-MS, 1H NMR and 13C NMR techniques. In vitro inhibitory activities of synthesized compounds on α-amylase, α-glucosidase and α-burylcholinesterase (α-BuChE) were evaluated using a purified enzyme assays. Compound 5c demonstrated strong and selective α-amylase inhibitory activity (IC50?=?1.1?μmol/g). 5?g exhibited excellent inhibition against α-glucosidase (IC50?=?1.2?μmol/g) when compared with acarbose (IC50?=?4.7?μmol/g) as a positive reference. Compound 5i was found to be most potent derivative against α-BuChE with the IC50 of 1.5?μmol/g which was comparable to the value obtained for (4.7?μmol/g) positive control (i.e. galantamine hydrobromide). Molecular dockings of synthesized compounds into the binding sites of human pancreatic α-amylase, intestinal maltase-glucoamylase and neuronal α-butrylcholinesterase allowed to shed light on the affinity and binding mode of these novel inhibitors. Preliminary structure–activity relationship (SAR) studies were carried out to understand the relationship between molecular structural features and inhibition activities of synthesized derivatives. These data suggested that compounds 5c, 5?g and 5i are promising candidates for hitto- lead follow-up in the drug-discovery process for the treatment of Alzheimer's disease and hyperinsulinamia.

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.

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.

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.

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.

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.