74467-05-3

Basic information

• Product Name: (Z)-N-hydroxy-4-(trifluoroMethyl)benziMidoyl chloride
• Synonyms: (Z)-N-hydroxy-4-(trifluoroMethyl)benziMidoyl chloride;N-Hydroxy-4-(trifluoromethyl)benzimidoyl chloride
• CAS NO: 74467-05-3
• Molecular Formula: C₈H₅ClF₃NO
• Molecular Weight: 223.5796096
• Mol File: 74467-05-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (Z)-N-hydroxy-4-(trifluoroMethyl)benziMidoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-N-hydroxy-4-(trifluoroMethyl)benziMidoyl chloride(74467-05-3)
• EPA Substance Registry System: (Z)-N-hydroxy-4-(trifluoroMethyl)benziMidoyl chloride(74467-05-3)

Safety Data

• Hazardous Substances Data: 74467-05-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(Z)-N-hydroxy-4-(trifluoroMethyl)benziMidoyl chloride is used as an intermediate in the synthesis of various pharmaceuticals. Its trifluoromethyl group contributes to the enhancement of bioactivity and metabolic stability, making it a crucial component in the development of effective drug compounds.
Used in Agrochemical Industry:
In the agrochemical industry, (Z)-N-hydroxy-4-(trifluoroMethyl)benziMidoyl chloride serves as an intermediate for the synthesis of agrochemicals. Its properties allow for the creation of compounds with improved bioactivity and stability, contributing to the effectiveness of these products.
Used in Organic Synthesis:
(Z)-N-hydroxy-4-(trifluoroMethyl)benziMidoyl chloride is used as a versatile building block in organic synthesis. Its reactivity and ability to undergo various chemical transformations make it a valuable component in the creation of a wide range of chemical compounds.
Used as a Coupling Reagent in Peptide Synthesis:
In the field of peptide synthesis, (Z)-N-hydroxy-4-(trifluoroMethyl)benziMidoyl chloride acts as a coupling reagent. Its properties facilitate the production of therapeutic peptides, making it an essential tool in the development of peptide-based drugs.

Upstream product

• 66046-34-2 4-(trifluoromethyl)benzaldehyde oxime 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 16939-49-4 (E)-4-(trifluoromethyl)benzaldoxime 

Downstream Products

• 74423-19-1 3'-<(4-trifluoromethyl)phenyl>spiro-3-one 
• 128413-22-9 2-phenyl-3'-<4-(trifluoromethyl)phenyl>spiro<1H-isoindole-1,5'(4'H)-isoxazol>-3(2H)-one 
• 128413-27-4 2-Benzyl-3-[2-[(E)-hydroxyimino]-2-(4-trifluoromethyl-phenyl)-eth-(E)-ylidene]-2,3-dihydro-isoindol-1-one 
• 128413-24-1 2-(phenylmethyl)-3'-<4-(trifluoromethyl)phenyl>spiro<1H-isoindole-1,5'(4'H)-isoxazol>-3(2H)-one 
• 1645-65-4 4-(trifluoromethyl)phenyl isothiocyanate 
• 150225-47-1 2-Methoxy-N-(4-trifluoromethyl-phenyl)-benzamide 
• 123476-73-3 4-Phenyl-3-(4-trifluoromethyl-phenyl)-4H-isoxazol-5-one 
• 159693-05-7 ethyl 3-(4-trifluoromethylphenyl)isoxazole-4-carboxylate 
• 159693-08-0 (3-(4-trifluoromethylphenyl)-5-methyl)isoxazole-4-carboxylic acid ethyl ester 
• 159693-10-4 5-Trifluoromethyl-3-(4-trifluoromethyl-phenyl)-isoxazole-4-carboxylic acid ethyl ester 
• 159693-12-6 5-(difluoromethyl)-3-[4-(trifluoromethyl)phenyl]-4-isoxazolecarboxylic acid, ethyl ester 
• 159693-13-7 ethyl 5-(pentafluoroethyl)-3-[4-(trifluoromethyl)phenyl]-4-isoxazolecarboxylate 
• 159693-15-9 methyl 5-(chlorodifluoromethyl)-3-[4-(trifluoromethyl)phenyl]-4-isoxazolecarboxylate 
• 233596-92-4 (4S,5S)-5-[(S)-hydroxy(trimethylsilyl)methyl]-4-methyl-3-[4-(trifluoromethyl)phenyl]-4,5-dihydroisoxazole 

Relevant articles and documents

Design, synthesis, anti-cancer activity and in-silico studies of some novel 4,5-dihydroisoxazole-5-carboxamide derivatives

A novel series of 4,5-dihydroisoxazole-5-carboxamide derivatives were designed, synthesized and evaluated for their anti-cancer activity against two different human cancer cell lines. Most of the synthesized compounds showed anti-cancer activity with ICs

Site selective synthesis and anti-inflammatory evaluation of Spiro-isoxazoline stitched adducts of arteannuin B

A library of new spiroisoxazoline analogues of arteannuin B was synthesized through 1, 3-dipolar cycloaddition in stereoselective fashion and consequently screened for anti-inflammatory activity in RAW 264.7 macrophage cells. Three potent analogues (8i, 8 m, and 8n) were found to attenuate the LPS induced release of cytokines IL-6 and TNF-α more potently than the parent molecule. Also, the inhibition of LPS induced nitric oxide production in these cells show moderate to high efficacy. None of the three potent molecules have altered the viability of RAW 264.7 cells following 48 h incubation suggesting that the inhibition of cytokines and nitric oxide production exhibited in the cells was not due to toxicity. In addition, these compounds exhibit an IC50 range of 0.17 μM-1.57 μM and 0.09 μM-0.35 μM for the inhibition of IL-6 release and nitric oxide production respectively. The results disclose potent inhibition of pro-inflammatory mediators which are encouraging and warrant further investigations to develop new therapeutic agents for inflammatory diseases.

Design and synthesis of sinomenine isoxazole derivatives via 1,3-dipolar cycloaddition reaction

A novel structure of sinomenine isoxazole derivatives is synthesised from sinomenine hydrochloride and aromatic aldehydes and requires six steps. 19 target compounds have been obtained in good yields. The sinomenine hydrochloride transforms to 4-alkynyl sinomenine, which is a key intermediate product to synthesise the target sinomenine isoxazole compounds, after a neutralisation reaction with ammonia and substitution reaction with 3-chloropropyne. Another key intermediate product is 1,3-dipole, which can be obtained from aromatic aldehyde. After treatment with hydroxylamine hydrochloride and then sodium carbonate solution, aromatic aldehyde is converted to aldehyde oxime, which reacts with N-chlorosuccinimide (NCS) to afford aryl hydroximino chloride. 1,3-Dipole is eventually formed in situ while triethylamine (TEA) in DMF is added dropwise. Then 4-alkynyl sinomenine is added to provide the sinomenine isoxazole derivative via 1,3-dipolar cycloaddition reaction as the key step. All the target compounds are characterised by melting point, 1H NMR, 13C NMR, HRMS and FT-IR spectroscopy.

Novel selective ido1 inhibitors with isoxazolo[5,4-d]pyrimidin-4(5h)-one scaffold

Indoleamine 2,3-dioxygenase 1 (IDO1) is a promising target in immunomodulation of several pathological conditions, especially cancers. Here we present the synthesis of a series of IDO1 inhibitors with the novel isoxazolo[5,4-d]pyrimidin-4(5H)-one scaffold. A focused library was prepared using a 6-or 7-step synthetic procedure to allow a systematic investigation of the structure-activity relationships of the described scaffold. Chemistry-driven modifications lead us to the discovery of our best-in-class inhibitors possessing p-trifluoromethyl (23), p-cyclohexyl (32), or p-methoxycarbonyl (20, 39) substituted aniline moieties with IC50 values in the low micromolar range. In addition to hIDO1, compounds were tested for their inhibition of indoleamine 2,3-dioxygenase 2 and tryptophan dioxygenase, and found to be selective for hIDO1. Our results thus demon-strate a successful study on IDO1-selective isoxazolo[5,4-d]pyrimidin-4(5H)-one inhibitors, defining promising chemical probes with a novel scaffold for further development of potent small-molecule immunomodulators.

Triazole alcohol derivative as well as preparation method and application thereof

The invention relates to a triazole alcohol derivative as well as a preparation method and application thereof. The chemical structure of the triazole alcohol derivative is shown as a formula I, R1 represents a benzene ring or a substituted benzene ring, and substituent groups of the substituted benzene ring can be located at all positions of the benzene ring, can be mono-substituted or multi-substituted, and can be selected from a) halogen which is F and Cl; b) an electron withdrawing group which is cyano or trifluoromethyl; c ) a lower alkyl of 1-4 carbon atoms or a halogen substituted loweralkyl; and d) lower alkoxy of 1-4 carbon atoms or halogen substituted lower alkoxy. The compound of the invention has strong antifungal activity, has the advantages of low toxicity, wide antibacterial spectrum and the like, and can be used for preparing antifungal drugs.

Design, synthesis, and in vitro evaluation of novel triazole analogues featuring isoxazole moieties as antifungal agents

In order to develop novel antifungal agents, based on our previous work, a series of (2R,3R)-3-((3-substitutied-isoxazol-5-yl)methoxy)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl) butan-2-ol (a1-a26) were designed and synthesized. All of the compounds exhibited good in vitro antifungal activities against eight human pathogenic fungi. Among them, compound a6 showed excellent inhibitory activity against Candida albicans and Candida parasilosis with MIC80 values of 0.0313 μg/mL. In addition, compounds a6, a9, a12, a13 and a14 exhibited moderate inhibitory activities against fluconazole-resistant isolates with MIC80 values ranging from 8 μg/mL to 16 μg/mL. Furthermore, compounds a6, a12 and a23 exhibited low inhibition profiles for CYP3A4. Clear SARs were analyzed, and the molecular docking experiment was carried out to further investigate the relationship between a6 and the target enzyme CYP51.

Discovery of Natural Product-Based Fungicides (II): Semisynthesis and Biological Activity of Sarisan Attached 3-Phenylisoxazolines as Antifungal Agents

Many phytopathogenic fungi cause severe damage to crop yields. In continuation of our research aimed at the discovery and development of natural products-based fungicides, a series of thirty-one sarisan attached 3-phenylisoxazolines were synthesized and evaluated for their antifungal activities against five phytopathogenic fungi (B. cinerea, C. lagenarium, A. solani, F. solani, and F. graminearum). Among all title sarisan derivatives, compounds IV2, IV14 and IV23 showed potent antifungal activity against some phytopathogenic fungi. In particular, compound IV2 exhibited a broad-spectrum and more potent antifungal activity against A. solani, F. solani, and F. graminearum than the commercial fungicide Hymexazol. In addition, compounds IV2, IV14 and IV23 also displayed relative low toxicity on normal NRK-52E cells. This work will give some insights into the development of sarisan derivatives as new fungicide candidates in plant protection.

Substituent effect study on the experimental 13C NMR chemical shifts of 3-(substituted phenyl)-3a,4,8,8a-tetrahydro-1,3-dioxepino[5,6-d] [1,2] isoxazoles

Novel heterocyclic derivatives containing isoxazole ring were synthesized by the 1,3-dipolar cycloaddition reaction of substituted nitrile oxides with cis-4,7-dihydro-1,3-dioxepin in the present study. These 3-(substituted phenyl)-3a,4,8,8a-tetrahydro-1,3

Palladium-Catalyzed Cyclization Reaction of Oxime Acetates and Aryl Iodides: Syntheses of 2-Imidazolines

A novel and versatile method for the synthesis of 2-imidazolines has been developed via the Pd-catalyzed cyclization reaction of readily available homoallenyl oxime acetates with aryl iodides. This protocol is performed under mild reaction conditions and needs no additives or ligands.

Preparation technology for 3-aryl-4-nitro isoxazole compound

The invention discloses a preparation technology for a 3-aryl-4-nitro isoxazole compound. The preparation technology comprises the following steps: synthesizing a compound shown as formula II through the nucleophilic addition of hydroxylamine hydrochloride and the compound shown as formula I used as the raw material; acquiring the compound shown as formula III through the substitution reaction of the compound shown as formula II and N-chlorosuccinimide; preparing 1-dimethyl amino-2-nitro ethylene through the reaction of N,N-dimethylformamide dimethyl acetal and nitromethane used as the raw material; and acquiring a target product 3-aryl-4-nitro isoxazole compound through the cyclization reaction of the compound shown as formula III and 1-dimethyl amino-2-nitro ethylene. The raw materials in the synthesis route are low in cost and easily acquired, the operation condition is mild and is easily controlled, the product is easily purified and the preparation technology is a new method for synthesizing the 3-aryl-4-nitro isoxazole compound.