22227-25-4

Usage

Uses

Used in Pharmaceutical Industry:
3-(TRIFLUOROMETHYL)BENZOIC ACID HYDRAZIDE is used as a key intermediate in the synthesis of various pharmaceutical compounds for the treatment of different diseases. Its unique chemical structure allows for the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
3-(TRIFLUOROMETHYL)BENZOIC ACID HYDRAZIDE is used as a potent inhibitor of plant pathogens, playing a crucial role in crop protection. Its ability to target and inhibit specific plant pathogens helps in reducing crop losses and improving agricultural productivity.
Used in Dye and Pigment Industry:
3-(TRIFLUOROMETHYL)BENZOIC ACID HYDRAZIDE is used as a starting material in the production of dyes and pigments. Its unique properties contribute to the development of high-performance dyes and pigments with improved color strength, stability, and resistance to various environmental factors.
Used in Specialty Chemicals Industry:
3-(TRIFLUOROMETHYL)BENZOIC ACID HYDRAZIDE is used in the synthesis of specialty chemicals, such as intermediates for the production of high-performance materials, catalysts, and other chemical compounds. Its versatility and unique properties make it a valuable component in the development of innovative specialty chemicals.

InChI:InChI=1/C8H7F3N2O/c9-8(10,11)6-3-1-2-5(4-6)7(14)13-12/h1-4H,12H2,(H,13,14)

Upstream product

• 58710-61-5 phenyl 3-(trifluoromethyl)benzoate 
• 76783-59-0 ethyl 3-(trifluoromethyl)benzoate 
• 454-92-2 3-(trifluoromethyl)benzoic acid 
• 2251-65-2 3-(Trifluoromethyl)benzoyl chloride 
• 2557-13-3 3-trifluoromethylbenzoic acid methyl ester 

Downstream Products

• 1450828-21-3 2-(3-(trifluoromethyl)phenyl)-1,3,4-oxadiazole 
• 1073613-02-1 3-trifluoromethyl-[[(4-carboxyphenyl)amino]thioxomethyl]benzoic acid hydrazide 
• 1340964-71-7 2-methyl-5-(3-(trifluoromethyl)phenyl)-1,3,4-oxadiazole 
• 286009-79-8 4-phenyl-3-(3-(trifluoromethyl)phenyl)-1H-1,2,4-triazole-5(4H)-thione 
• 1334627-21-2 5-(3-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2(3H)-one 
• 1450828-20-2 N'-(2,2,2-trifluoroacetyl)-3-(trifluoromethyl)benzohydrazide 
• 1450828-19-9 methyl 2-(3-(trifluoromethyl)benzoyl)hydrazinecarboxylate 
• 1477520-15-2 5-(3-(trifluoromethyl)phenyl)-1,3,4-oxadiazole-2-carboxamide 
• 1450828-23-5 2-(trifluoromethyl)-5-(3-(trifluoromethyl)phenyl)-1,3,4-oxadiazole 
• 1450828-22-4 2-methoxy-5-(3-(trifluoromethyl)phenyl)-1,3,4-oxadiazole 
• 1432053-94-5 ethyl 5-(3-(trifluoromethyl)phenyl)-1,3,4-oxadiazole-2-carboxylate 
• 1456613-74-3 5-thioxo-2-(3-(trifluoromethyl)phenyl)-5,6-dihydro-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one 
• 1456614-02-0 C₁₃H₁₂F₃N₅O₂S 
• 502686-01-3 C₉H₇F₃N₄ 

Relevant academic research and scientific papers

Synthesis of benzoyl hydrazones having 4-hydroxy-3,5-dimethoxy phenyl ring, their biological activities, and molecular modeling studies on enzyme inhibition activities

Hydrazone compounds have high capacity in terms of antioxidant activity and enzyme inhibition activities such as anticholinesterase, tyrosinase, and urease. In this study, benzoyl hydrazones compounds (7a-7m) were synthesized starting from 3,5-dimethoxy-4

4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors

In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.

Manipulating peripheral non-conjugated substituents in carbazole/oxadiazole hybrid TADF emitters towards high-efficiency OLEDs

The chemical modification of existing thermally activated delayed fluorescence (TADF) materials is a simple strategy to increase the luminescence efficiency and is also favorable for a deeper understanding of the structure-property relationship. In this work, based on a previous multi-functional carbazole/oxadiazole hybrid light-blue TADF emitter 2-(2,3,4,5,6-penta(9H-carbazol-9-yl)phenyl)-5-phenyl-1,3,4-oxadiazole (5CzOXD), a series of 5CzOXD derivatives have been designed by rationally introducing non-conjugated electron-donatingtert-butyl (t-Bu) units at the 3- and 6-positions of carbazole and/or electron-withdrawing trifluoromethyl (CF3) units at thepara- ormeta-positions of the terminal phenyl ring in the diphenyl-1,3,4-oxadiazole group. The TADF emission colors were slightly affected by non-conjugated peripheral substituents, while a singlet-triplet band gap (ΔEST) value could be easily tuned from 0.24 to ～0 eV. It is interesting that through step-by-step chemical modification, progressively increased photoluminescence (22-88%) and electroluminescence (2.3-13.7%) quantum efficiencies could be achieved for the TADF emitters in doped films of theo-CzOXD host matrix. Similar trends were also obtained for 26DCzPPy-hosted TADF OLEDs. For example, bare 5CzOXD showed a maximum external quantum efficiency (EQE) of 8.7%, the value oft-Bu-modified 5tCzOXD was increased to 14.2%, and even higher EQE values in the range of 20-22% were obtained fort-Bu and single CF3-substitutedmCF35tCzOXD andpCF35tCzOXD. The best EQE value of 23.3% was achieved for dCF35tCzOXD by synergisticalt-Bu and double CF3-substitution due to its ～0 eV of ΔESTfor a significantly increased reverse intersystem crossing rate and a decreased triplet non-radiative decay rate. This work provides an effective strategy for achieving high-efficiency TADF OLEDs through the modification of currently less efficient TADF emitters.

Design, Synthesis, and Study of the Insecticidal Activity of Novel Steroidal 1,3,4-Oxadiazoles

A series of novel steroidal derivatives with a substituted 1,3,4-oxadiazole structure was designed and synthesized, and the target compounds were evaluated for their insecticidal activity against five aphid species. Most of the tested compounds exhibited potent insecticidal activity against Eriosoma lanigerum (Hausmann), Myzus persicae, and Aphis citricola. Compounds 20g and 24g displayed the highest activity against E. lanigerum, showing LC50 values of 27.6 and 30.4 μg/mL, respectively. Ultrastructural changes in the midgut cells of E. lanigerum were detected by transmission electron microscopy, indicating that these steroidal oxazole derivatives might exert their insecticidal activity by destroying the mitochondria and nuclear membranes in insect midgut cells. Furthermore, a field trial showed that compound 20g exhibited effects similar to those of the positive controls chlorpyrifos and thiamethoxam against E. lanigerum, reaching a control rate of 89.5% at a dose of 200 μg/mL after 21 days. We also investigated the hydrolysis and metabolism of the target compounds in E. lanigerum by assaying the activities of three insecticide-detoxifying enzymes. Compound 20g at 50 μg/mL exhibited inhibitory action on carboxylesterase similar to the known inhibitor triphenyl phosphate. The above results demonstrate the potential of these steroidal oxazole derivatives to be developed as novel pesticides.

N-(1-CYANO-PYRROLIDIN-3-YL)-5-(3-(TRIFLUOROMETHYL)PHENYL)OXAZOLE-2-CARBOXAMIDE DERIVATIVES AND THE CORRESPONDING OXADIAZOLE DERIVATIVES AS USP30 INHIBITORS FOR THE TREATMENT OF MITOCHONDRIAL DYSFUNCTION

The present invention relates to a class of N-cyanopyrrolidines with activity as inhibitors of the deubiquitylating enzyme USP30, having utility in a variety of therapeutic areas, including conditions involving mitochondrial dysfunction, cancer and fibros

Synthesis, fungicidal activity, and 3D-QSAR of tetrazole derivatives containing phenyloxadiazole moieties

In an effort to discover new agents with good fungicidal activities against CDM (cucumber downy mildew), a series of tetrazole derivatives containing phenyloxadiazole moieties were designed and synthesized. The EC50 values for fungicidal activities against CDM were determined. Bioassay results indicated that most synthesized compounds exhibited potential in vivo fungicidal activity against CDM. A CoMFA (comparative molecular field analysis) model based on the bioactivity was developed to identify some primary structural quality for the efficiency. The values of q2 and r2 for the established model were 0.791 and 0.982 respectively, which reliability and predict abilities were verified. Three analogues (q3, q4, q5) were designed and synthesized based on the model. All these compounds exhibited significant fungicidal activity on CDM with the EC50 of 1.43, 1.52, 1.77 mg·L?1. This work could provide a useful instruction for the further structure optimization.

Designing heterocyclic chalcones, benzoyl/sulfonyl hydrazones: An insight into their biological activities and molecular docking study

The aim of this study is to investigate the antioxidant, anticholinesterase and the antiproliferative activities of some chalcones, benzoyl and sulfonyl hydrazones. The antioxidant activity was studied by way of four complimentary assays and the anticholinesterase activity was studied using the Ellman method. The antiproliferative activity of the compounds was determined using a BrdU cell proliferation ELISA assay. Compound 32 (IC50: 15.58 ± 0.01 μg/mL) against the brain (C6) and 29 (IC50: 5.02 ± 0.05 μg/mL) against cervical (HeLa) cancer cell lines exhibited higher antiproliferative activity than the other compounds. Two sulfonyl hydrazone derivatives 45 and 47 exhibited very good antioxidant activity. The results of anticholinesterase activity indicated that nine compounds 3, 8, 10, 14, 24, 25, 27, 38, and 45 significantly inhibited acetylcholinesterase enzymes and thirty-three compounds 1–4, 7–14, 22–28, 32–41, 44–47 inhibited butyrylcholinesterase enzymes (BChE) more than galantamine. In addition, virtual screening methods based on ligand 45 having the best activity against BChE was used to define new human BChE inhibitors. The interactions of ligand 8 against acetylcholinesterase (AChE) were also examined. Important key residues were determined and visualized on completion of the methodology. All calculations indicated the suitability of use of the molecular docking approach for understanding interaction mechanisms and crucial fragments of novel hit compounds such as the potential lead AChE and BChE inhibitor candidates.

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.

4-Amino-1,2,4-triazole-3-thione-derived Schiff bases as metallo-β-lactamase inhibitors

Resistance to β-lactam antibiotics in Gram-negatives producing metallo-β-lactamases (MBLs) represents a major medical threat and there is an extremely urgent need to develop clinically useful inhibitors. We previously reported the original binding mode of 5-substituted-4-amino/H-1,2,4-triazole-3-thione compounds in the catalytic site of an MBL. Moreover, we showed that, although moderately potent, they represented a promising basis for the development of broad-spectrum MBL inhibitors. Here, we synthesized and characterized a large number of 4-amino-1,2,4-triazole-3-thione-derived Schiff bases. Compared to the previous series, the presence of an aryl moiety at position 4 afforded an average 10-fold increase in potency. Among 90 synthetic compounds, more than half inhibited at least one of the six tested MBLs (L1, VIM-4, VIM-2, NDM-1, IMP-1, CphA) with Ki values in the μM to sub-μM range. Several were broad-spectrum inhibitors, also inhibiting the most clinically relevant VIM-2 and NDM-1. Active compounds generally contained halogenated, bicyclic aryl or phenolic moieties at position 5, and one substituent among o-benzoic, 2,4-dihydroxyphenyl, p-benzyloxyphenyl or 3-(m-benzoyl)-phenyl at position 4. The crystallographic structure of VIM-2 in complex with an inhibitor showed the expected binding between the triazole-thione moiety and the dinuclear centre and also revealed a network of interactions involving Phe61, Tyr67, Trp87 and the conserved Asn233. Microbiological analysis suggested that the potentiation activity of the compounds was limited by poor outer membrane penetration or efflux. This was supported by the ability of one compound to restore the susceptibility of an NDM-1-producing E. coli clinical strain toward several β-lactams in the presence only of a sub-inhibitory concentration of colistin, a permeabilizing agent. Finally, some compounds were tested against the structurally similar di-zinc human glyoxalase II and found weaker inhibitors of the latter enzyme, thus showing a promising selectivity towards MBLs.

Synthesis and bioactivity of sulfide derivatives containing 1,3,4-oxadiazole and pyridine

A series of novel sulfide derivatives containing 1,3,4-oxadiazole and pyridine were synthesized, characterized, and tested for their antibacterial activity against tobacco bacterial wilt and rice bacterial blight and for insecticidal activity toward diamondback moth. The results showed that some compounds had good insecticidal and bactericidal activity, e.g., the activities of compounds 6e and 6g–6j toward tobacco bacterial wilt were much better than those of commercial thiodiazole-copper, and some of the synthesized compounds possessed good insecticidal activity against Plutella xylostella. Compounds 6d, 6h, 6j, 6l, 6p, 6r, and 6p displayed over 93% activity at 500 mg L? 1.