339-59-3

Usage

Uses

Used in Pharmaceutical Industry:
4-(TRIFLUOROMETHYL)BENZHYDRAZIDE is used as a reagent for the synthesis of benzoyl hydrazone derivatives, which exhibit fungicidal activity. This makes it a valuable component in the development of new antifungal agents to combat fungal infections.
In the synthesis process, 4-(TRIFLUOROMETHYL)BENZHYDRAZIDE reacts with appropriate benzoyl compounds to form the desired benzoyl hydrazone derivatives. These derivatives have potential applications in medicinal chemistry, particularly in the treatment of fungal infections due to their fungicidal properties. The use of this reagent allows for the creation of a diverse range of benzoyl hydrazone derivatives with varying structures and activities, providing a broad scope for research and development in the pharmaceutical industry.

InChI:InChI=1/C18H17ClFNO3/c1-3-24-18(23)12(2)21(14-9-10-16(20)15(19)11-14)17(22)13-7-5-4-6-8-13/h4-12H,3H2,1-2H3

Upstream product

• 583-02-8 ethyl 4-(trifluoromethyl)benzoate 
• 2967-66-0 methyl 4-(trifluoromethyl)benzoate 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 1391436-65-9 sodium 2-[(4-triflouromethyl-benzoyl)-hydrazono]-propionate 
• 106376-16-3 p-trifluoromethylbenzoic acid phenyl ester 

Downstream Products

• 389120-03-0 5-[4-(Trifluoromethyl)phenyl]-1,3,4-oxadiazole-2-thiol 
• 355823-35-7 C₂₁H₂₀ClF₃N₃O₇PS 
• 857028-64-9 C₁₅H₁₂F₃N₃O₂ 
• 497946-53-9 2-methyl-5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazole 
• 17605-88-8 3,5-dimethyl-1-(p-trifluoromethylbenzoyl)pyrazole 
• 816458-31-8 Tecovirimat 
• 202823-22-1 5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-(3H)-one 
• 202822-66-0 3-[(2-methoxyphenyl)-methyl]-5-[4-(trifluoromethyl)phenyl]1,3,4-oxadiazol-2-(3H)-one 

Relevant academic research and scientific papers

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.

Pleuromutilin derivative with 1, 3, 4-oxadiazole side chain and preparation and application thereof

The invention belongs to the field of medicinal chemistry, and particularly relates to a pleuromutilin derivative with a 1, 3, 4-oxadiazole side chain and preparation and application thereof The pleuromutilin derivative with the 1, 3, 4-oxadiazole side chain is a compound shown in a formula 2 or a pharmaceutically acceptable salt thereof, and a solvent compound, an enantiomer, a diastereoisomer and a tautomer of the compound shown in the formula 2 or the pharmaceutically acceptable salt thereof or a mixture of the solvent compound, the enantiomer, the diastereoisomer and the tautomer in any proportion, including a racemic mixture. The pleuromutilin derivative has good antibacterial activity, is especially suitable for being used as a novel antibacterial agent for systemic system infection of animals or human beings, and has good water solubility.

Hydrazones of 4-(Trifluoromethyl)benzohydrazide as new inhibitors of acetyl- and butyrylcholinesterase

Based on the broad spectrum of biological activity of hydrazide-hydrazones, trifluoromethyl compounds, and clinical usage of cholinesterase inhibitors, we investigated hydrazones obtained from 4-(trifluoromethyl)benzohydrazide and various benzaldehydes or aliphatic ketones as potential inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). They were evaluated using Ellman’s spectrophotometric method. The hydrazide-hydrazones produced a dual inhibition of both cholinesterase enzymes with IC50 values of 46.8-137.7 μM and 19.1-881.1 μM for AChE and BuChE, respectively. The majority of the compounds were stronger inhibitors of AChE; four of them (2-bromobenzaldehyde, 3-(trifluoromethyl)benzaldehyde, cyclohexanone, and camphor-based 2o, 2p, 3c, and 3d, respectively) produced a balanced inhibition of the enzymes and only 2-chloro/trifluoromethyl benzylidene derivatives 2d and 2q were found to be more potent inhibitors of BuChE. 4-(Trifluoromethyl)-N’-[4-(trifluoromethyl)benzylidene]benzohydrazide 2l produced the strongest inhibition of AChE via mixed-type inhibition determined experimentally. Structure-activity relationships were identified. The compounds fit physicochemical space for targeting central nervous systems with no apparent cytotoxicity for eukaryotic cell line together. The study provides new insights into this CF3-hydrazide-hydrazone scaffol.

Design, synthesis, and biological evaluation of phenyloxadiazole derivatives as potential antifungal agents against phytopathogenic fungi

Abstract: A novel series of picarbutrazox-inspired oxadiazole hybrids was synthesized and the derivatives’ biological activity against phytopathogenic fungi was investigated. The molecules were designed by retaining the active fragment of tetrazolyl phenyloxime ether of lead compound picarbutrazox, while introducing the potentially active oxadiazole-derived fragment. Bioassay results revealed that some of the title compounds showed potent in vivo antifungal activities to control cucumber downy mildew. Therefore, this novel oxadiazole phenyloxadiazole derivative can be used as a potential antifungal agent to control cucumber downy mildew and other phytopathogenic fungi for crop protection. Graphic abstract: [Figure not available: see fulltext.].

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.

INHIBITOR COMPOUNDS

The disclosure relates to heterocyclic compounds and methods for their preparation. The disclosure provides compounds that may have beneficial therapeutic activity in the treatment of a disease or condition mediated by excessive or otherwise undesirable Des1 and/or fibrotic activity.

Design, synthesis, and evaluation of N-benzylpyrrolidine and 1,3,4-oxadiazole as multitargeted hybrids for the treatment of Alzheimer's disease

Novel N-Benzylpyrrolidine hybrids were designed, synthesized, and tested against multiple in-vitro and in-vivo parameters. Among all the synthesized molecules, 8f and 12f showed extensive inhibition against beta-secretase-1 (hBACE-1), human acetylcholinesterase (hAChE) & human butyrylcholinesterase (hBuChE). These molecules are also endowed with significant AChE-peripheral anionic site (PAS) binding capability, blood-brain barrier permeability, potential disassembly of Aβ aggregates along with neuroprotection ability on SHSY-5Y cell lines. Results of the Y-Maze and Morris water maze test concluded that compounds 8f and 12f ameliorated cognitive dysfunction induced by scopolamine and Aβ. The ex-vivo activity was executed on rat's brain homogenate indicating a reduction in AChE level and oxidative stress. The pharmacokinetic investigation ascertained considerable oral absorption profile of the lead 12f. The results of the in silico docking studies and molecular dynamics simulations demonstrated stable interactions of compounds 8f and 12f with the target residues of hAChE, hBuChE and hBACE-1.

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.

Synthesis of isoquinolones by visible-light-induced deaminative [4+2] annulation reactions

Herein a metal-free approach for the synthesis of isoquinolone derivatives by means of photoinitiated deaminative [4+2] annulation of alkynes and N-amidepyridinium salts is described. This protocol exhibits a broad scope and good functional group tolerance and regioselectivity under benign reaction conditions. Preliminary studies suggest that the critical amide radical is derived from the photocatalytic cleavage of the N-N bond of the N-amidepyridinium salt, which adds to the triple bond of the alkyne and undergoes the annulation process to afford the desired isoquinolones.

Aromatic acyl hydrazone derivative and application thereof as NA inhibitor

The invention relates to an aromatic acyl hydrazone derivative as shown in a structural formula I, pharmaceutically acceptable salt and a pharmaceutical composition thereof, and application of the aromatic acyl hydrazone derivative and the pharmaceutically acceptable salt and the pharmaceutical composition in preparation of an influenza virus neuraminidase inhibitor, wherein R is one of trifluoromethyl, nitryl, 3-methyl-4-nitryl, 3-hydroxyl-4-nitryl, 3-nitryl-4-hydroxyl, hydroxyl, dihydroxyl, dinitryl, 3-methoxy-4-hydroxyl or trihydroxyl; Y is selected from hydroxyl, dihydroxyl, 2-hydroxyl-3-methoxy, 2-hydroxyl-4-methoxy,2-hydroxyl-5-methoxy,2-hydroxyl-6-methoxy,3-hydroxyl-2-methoxy,3-hydroxyl-4-methoxy,3-hydroxyl-5-methoxy,3-hydroxyl-6-methoxy,4-hydroxyl-2-methoxy,4-hydroxyl-3-methoxy,4-hydroxyl-3,5-dimethoxy, trihydroxyl, 4-hydroxyl-3-ethoxy, or 4-hydroxyl-3,5-dimethoxy; w is selected from CH or N; and z is selected from CH or N.