21953-91-3

Usage

Uses

Used in Agriculture:
(4-METHOXY-PHENOXY)-ACETIC ACID HYDRAZIDE is used as a herbicide for controlling the growth of weeds and unwanted vegetation in agricultural fields. It inhibits the biosynthesis of branched chain amino acids in plants, thereby restricting their growth.
(4-METHOXY-PHENOXY)-ACETIC ACID HYDRAZIDE is also used as a plant growth regulator to manage the growth of certain crops, ensuring optimal yield and quality.
Used in Control of Parasitic Weeds:
(4-METHOXY-PHENOXY)-ACETIC ACID HYDRAZIDE is used as a pre-emergent herbicide to control parasitic weeds in crops, protecting the plants from damage caused by these invasive species.
Used in Pharmaceutical Research:
(4-METHOXY-PHENOXY)-ACETIC ACID HYDRAZIDE is being researched for its potential use as a treatment for tuberculosis. Its ability to inhibit the growth of mycobacteria, the bacteria responsible for tuberculosis, makes it a promising candidate for further investigation and development as an anti-tuberculosis agent.

InChI:InChI=1/C9H12N2O3/c1-13-7-2-4-8(5-3-7)14-6-9(12)11-10/h2-5H,6,10H2,1H3,(H,11,12)

Upstream product

• 18598-23-7 ethyl (4-methoxyphenoxy)acetate 
• 1877-75-4 2-(4-methoxyphenoxy)acetic acid 
• 150-76-5 4-methoxy-phenol 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 84816-35-3 (4-Methoxy-phenoxy)-acetic acid [5-bromo-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-hydrazide 
• 107951-86-0 C₁₇H₁₉N₃O₃S 
• 107951-85-9 C₁₆H₁₇N₃O₃S 
• 107951-87-1 C₁₆H₁₆ClN₃O₃S 
• 107951-90-6 C₁₇H₁₉N₃O₄S 
• 107951-88-2 C₁₆H₁₆ClN₃O₃S 
• 107951-89-3 4-(p-ethoxyphenyl)-1-(p-methoxyphenoxyacetyl)thiosemicarbazide 
• 107951-91-7 C₂₀H₁₉N₃O₃S 
• 166274-72-2 Furan-2-carboxylic acid {N'-[2-(4-methoxy-phenoxy)-acetyl]-hydrazinocarbothioyl}-amide 
• 300661-55-6 4-chloro-N-{N'-[(4-methoxy-phenoxy)-acetyl]-hydrazinocarbothioyl}-benzamide 
• 337919-45-6 1-(4-methoxyphenyloxyacetyl)-4-(4-tolyloxyacetyl)thiosemicarbazide 
• 364331-66-8 1-(4-methoxyphenyloxyacetyl)-4-(5-(4-chlorophenyl)-2-furoyl)thiosemicarbazide 
• 180798-33-8 4-bromo-N-{N'-[(4-methoxy-phenoxy)-acetyl]-hydrazinocarbothioyl}-benzamide 

Relevant academic research and scientific papers

Identification and synthesis of selective cholesterol esterase inhibitor using dynamic combinatorial chemistry

In this study, the concept of dynamic combinatorial chemistry (DCC) was applied to explore novel cholesterol esterase (CEase) inhibitors. In the presence of enzyme, two substrates (A1H3 and A2H3) were amplified from the dynamic combinatorial library (DCL), which was generated through reversible acylhydrazone formation reaction. In the in vitro biological evaluation, compound A1H3 exhibited not only potent (IC50 in nanomolar range) but also selective inhibition (>120 folds of selectivity for CEase over AChE). Furthermore, the binding pattern and possible binding mechanism were investigated in the kinetic experiment and molecular docking study, respectively.

N-Amino-1,8-Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono-N-Substituted Hydrazines and Hydrazides

A new route to synthesis of various mono-N-substituted hydrazines and hydrazides by involving in a new C?N bond formation by using N-amino-1,8-naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8-naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C?N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N-amino-1,8-naphthalimide is suitable synthon for transformation for selective formation of mono-substituted hydrazine and hydrazide derivatives. Those are selective mono-amidation of hydrazine with acid halides; mono-N-substituted hydrazones from aldehydes; synthesis of N-aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N-dibenzylhydrazines and N-benzylhydrazines from benzyl halides; synthesis of N-amino-amino acids from α-halo esters. Ecofriendly reagent N-amino-1,8-naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.

Design, synthesis and molecular modelling of phenoxyacetohydrazide derivatives as Staphylococcus aureus MurD inhibitors

In the present work we synthesized a new series of phenoxyacetohydrazide functional compounds 4a-k and characterized by spectral data. Synthesized compounds were screened in vitro for their antibacterial activity. Compounds 4a, 4j and 4k exhibited inhibitory activity against S. aureus NCIM 5022 with MIC value of 64?μg/ml These compounds also exhibited activity against methicillin resistant S. aureus ATCC 43300 with MIC of 128?μg/ml. Among all the tested compounds 4c and 4j showed highest activity, respectively against B. subtilis NCIM 2545 and K. pneumoniae NCIM 2706. Only one compound i.e. 4d showed activity against another Gram-negative bacteria P. aeruginosa NCIM 2036 with MIC value of 64?μg/ml. Among three tested compounds, 4k exhibited highest inhibitory activity against S. aureus MurD enzyme with IC50 value of 35.80?μM. Further binding interactions of 4a-k with the modelled S. aureus MurD catalytic pocket residues is investigated with the extra-precision molecular docking and binding free energy calculation by MM-GBSA approach. The van der Waals energy term was observed to be the driving force for binding. Further, 50?ns molecular dynamics simulations were performed to validate the stabilities of 4j- and 4k-modelled S. aureus MurD. Graphic abstract: [Figure not available: see fulltext.]

Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment

Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.

Synthesis and luminescence properties of novel 8-hydroxyquinoline derivatives and their Eu(III) complexes

Six novel 8-hydroxyquinoline derivatives were synthesized using 2-methyl-8-hydroxyquinoline and para-substituted phenol as the main starting materials, and were characterized by 1H nuclear magnetic resonance (NMR), mass spectrometry (MS), ultraviolet (UV) light analysis and infra-red (IR) light analysis. Their complexes with Eu(III) were also prepared and characterized by elemental analysis, molar conductivity, UV light analysis, IR light analysis, and thermogravimetric–differential thermal analysis (TG–DTA). The results showed that the ligand coordinated well with Eu(III) ions and had excellent thermal stability. The structure of the target complex was EuY1–6(NO3)3.2H2O. The luminescence properties of the target complexes were investigated, the results indicated that all target complexes had favorable luminescence properties and that the introduction of an electron-donating group could enhance the luminescence intensity of the corresponding complexes, but the addition of an electron-withdrawing group had the opposite effect. Among all the target complexes, the methoxy-substituted complex (–OCH3) had the highest fluorescence intensity and the nitro-substituted complex (–NO2) had the weakest fluorescence intensity. The results showed that 8-hydroxyquinoline derivatives had good energy transfer efficiency for the Eu(III) ion. All the target complexes had a relatively high fluorescence quantum yield. The fluorescence quantum yield of the complex EuY3(NO3)3.2H2O was highest among all target complexes and was up to 0.628. Because of excellent luminescence properties and thermal stabilities of the Eu(III) complexes, they could be used as promising candidate luminescent materials.

Synthesis and larvicidal activity of 1,3,4-oxadiazole derivatives containing a 3-chloropyridin-2-yl-1H-pyrazole scaffold

Abstract: A new series of 1,3,4-oxadiazole derivatives with a 3-chloropyridin-2-yl-1H-pyrazole moiety was designed, synthesized, and characterized. The results of bioassay against Helicoverpa armigera and Plutella xylostella indicated that some of the synthesized compounds showed remarkable larvicidal activity. In particular, the LC50 values of the most active compounds against P. xylostella were 46.5, 23.9, and 13.9?mg/dm3, and against Helicoverpa armigera were 88.3 and 69.5?mg/dm3, the latter being slightly better than commercial chlorpyrifos (LC50 103.77?mg/dm3). Preliminary SAR was also discussed. Graphical abstract: [Figure not available: see fulltext.].

Synthesis, Nematicidal Activity, and 3D-QSAR of Novel 1,3,4-Oxadiazole/ Thiadiazole Thioether Derivatives

Forty one novel 1,3,4-oxadiazole/thiadiazole thioether derivatives containing phenoxy moiety were designed and synthesized. Bioassay demonstrated that some of them showed remarkable activities against Tylenchulus semipenetrans in vitro and in vivo. Compounds 20, 21, 35 and 39 showed excellent lethal activities after treatment for 48?h in vitro, with LC50 values of 13.4?±?1.8, 11.7?±?2.5, 13.7?±?2.4 and 13.3?±?1.1?mg·L–1, respectively, which were obviously superior to fosthiazate (49.1?±?2.8?mg·L–1) and avermectin (26.6?±?2.3?mg·L–1). Compound 21 can effectively control the citrus nematode disease caused by T. semipenetrans at 200?mg·L–1 in vivo with (68?±?3)% inhibitory effect, which was even better than that of avermectin ((63?±?2)%). The CoMFA and CoMSIA models of three-dimensional quantitative structure-activity relationships (3D-QSARs) were established. The compound 33 was designed based on the 3D-QSAR models with more vigorous nematicidal activities in vitro (LC50?=?9.8?±?1.4?mg·L–1) and in vivo ((70?±?5)%). These results demonstrated that compound 33 can be considered as a potential nematicide.

Synthesis and biological evaluations of some new oxadiazole–piperidine hybrid derivatives as antioxidant agents

A series of some new 1,3,4-oxadiazole-2-thiol derivatives (6a-h) containing cyclic secondary amine such as piperidine ring was expeditiously synthesized by alkylation of 1,3,4-oxadiazol-2-thiol derivatives with chloroethyl piperidine hydrochloride. The 1,3,4-oxadiazole-2-thiols were effectively synthesized by cyclization reaction of acid hydrazide derivatives with carbon disulfide. The target compounds 6a-h were preliminarily screened for in vitro antioxidant activities using various in vitro antioxidant assays including 2,2′-diphenyl-1-picrylhydrazyl, nitric oxide, and hydrogen peroxide methods. The results showed that the compounds exhibited promising antioxidant property in the three methods at 50, 75, and 100 μM. Among the tested compounds, the compounds 6a and 6b having chloro substituent in the benzene ring displayed greater radical scavenging activity.

2,5-substituent-1,3,4-oxadiazole (thiadiazole) thioether derivatives as well as preparation method and application thereof

The invention discloses 2,5-substituent-1,3,4-oxadiazole (thiadiazole) thioether derivatives as well as a preparation method and an application thereof. The 2,5-substituent-1,3,4-oxadiazole (thiadiazole) thioether derivatives have the general formula (I) shown in the following specification, wherein R1 represents as 4-chlorphenyl, 4-fluorophenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-cyano-3,5-difluorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, 4-t-butylphenyl, 2-fluorophenyl and other substituents; R2 represents methyl, ethyl, 4-chlorobenzyl, 2,4-dichlorobenzyl, 4-trifluoromethoxy, benzyl, 4-fluorobenzyl, 4-chlorobenzyl and other substituents; X represents O or S. The compound can be used as a pesticide for killing crop nematode and inhibiting bacterial diseases of crops.

Synthesis of oxadiazole-morpholine derivatives and manifestation of the repressed CD31 Microvessel Density (MVD) as tumoral angiogenic parameters in Dalton's Lymphoma

A series of oxadiazole derivatives possessing morpholine 6a-l were synthesized by nucleophilic substitution reaction of key intermediates [1,3,4]-oxadiazole-2-thiol derivatives 5a-l with 4-(2-chloroethyl) morpholine. Compounds 6a-l were evaluated for their in vitro and in vivo antitumor potential in Dalton's Lymphoma Ascites (DLA) tumor cells. Among 6a-l series, compound 6a with concentration ～8.5 μM have shown extensive cytotoxicity in vitro and 85% reduction in tumor volume in vivo, attributing an excellent anti-proliferative capability towards the cancer cells. Compound 6a has extensively inhibited the Microvessel Density (MVD) or tumoral neovasculature which was evident from the CD31 immuno staining and peritoneal H&E staining. The major reason for the antiproliferative activity of compound 6a was due to the repression of tumor vasculature.