4664-55-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenoxyacetohydrazide is used as an intermediate in the synthesis of pharmaceuticals for its potential anti-tumor properties. It is being studied for its ability to target and inhibit the growth of cancer cells, offering a potential therapeutic option for various types of cancer.
Used in Agricultural Industry:
2-Phenoxyacetohydrazide is used as a herbicide and plant growth regulator in agriculture. Its application helps control the growth of unwanted plants and promotes the healthy development of crops, contributing to increased agricultural productivity.
Used in Anti-inflammatory Applications:
2-Phenoxyacetohydrazide is used as an anti-inflammatory agent for its potential to reduce inflammation and alleviate pain. Its anti-inflammatory properties make it a candidate for the development of medications to treat various inflammatory conditions.
Safety Precautions:
Although 2-Phenoxyacetohydrazide is considered to have low toxicity, it should be handled with care and used in accordance with proper safety precautions to minimize any potential risks to human health and the environment.

InChI:InChI=1/C8H10N2O2/c9-10-8(11)6-12-7-4-2-1-3-5-7/h1-5H,6,9H2,(H,10,11)

Upstream product

• 2555-49-9 phenoxyacetic acid ethyl ester 
• 2065-23-8 methyl 2-phenoxyacetate 
• 122-59-8 2-phenoxyacetic acid 
• 108-95-2 phenol 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 84816-32-0 5-bromo-3-phenoxy acetyl hydrazono-2-indolinone 
• 157063-62-2 phenoxy-acetic acid cyclohexylidenehydrazide 
• 52093-72-8 1-phenoxyacetyl-2-benzylidenehydrazine 
• 106595-97-5 1-phenoxyacetyl-2-(2-hydroxybenzylidene)hydrazine 
• 52093-73-9 phenoxy-acetic acid-(1-phenyl-ethylidenehydrazide) 
• 36140-85-9 3,5-dimethyl-1-phenoxyacetyl-1H-pyrazole 
• 320423-94-7 phenoxy-acetic acid benzhydrylidenehydrazide 
• 21520-88-7 5-phenoxymethyl-[1,3,4]oxadiazol-2-ylamine 
• 53961-95-8 2-phenoxy-N'-(2-phenoxyacetyl)-acetohydrazide 
• 112535-61-2 phenoxymethyl-carbamic acid isopropyl ester 
• 99359-96-3 phenoxymethyl-carbamic acid-(2-chloro-ethyl ester) 
• 100866-80-6 phenoxymethyl-carbamic acid phenyl ester 

Relevant academic research and scientific papers

Synthesis and Antimicrobial Evaluation of Novel Derivatives of Semicarbazide and 1,2,4-triazole

Reaction of phenoxyacetic acid hydrazide with isocyanate was used to the synthesis of new semicarbazide derivatives. Cyclization of these compounds in a 2% aqueous solution of sodium hydroxide led to formation of 1,2,4-triazole-3-one. The chemical structure of synthesized compounds was confirmed by elemental analysis and spectroscopic methods (1H and 13C NMR). On the basis of the NMR, spectra were found that cyclic compounds 1,2,4-triazole exist in the -one form. Moreover, all derivatives were examined for their in vitro activity against some species of bacteria. New compounds presented mild or moderate antimicrobial activity only against reference Gram-positive bacteria. Two derivatives (one semicarbazide and one triazole) showed bactericidal or bacteriostatic activity.

Anion sensing using colorimetric amidourea based receptors incorporated into a 1,3-disubstituted calix[4]arene

The synthesis of amidourea-based colorimetric anion sensors 1 and 2 and the evaluation of these sensors using anions such as acetate (CH3 CO2-), fluoride (F-), hydrogen phosphate (H2 PO4su

Novel phenolic Mannich base derivatives: synthesis, bioactivity, molecular docking, and ADME-Tox Studies

In this study, it was aimed to synthesize novel molecules containing potential biological active phenolic Mannich base moiety and evaluate the inhibition properties against α-glycosidase (α-Gly) and acetylcholinesterase (AChE). For this purpose, phenolic aldehydes (1–3) were synthesized from 4-hydroxy-3-methoxy benzaldehyde (vanillin) according to the Mannich Reaction. Five different carboxylic acid hydrazides (4a-e) were synthesized from esters obtained from carboxylic acids. Fifteen Schiff base derivatives (5a-e, 6a-e, and 7a-e) were synthesized from the condensation reaction of compounds 1–3 with 4a-e. In this work, a series of novel Schiff bases from Phenolic Mannich bases (5a-e, 6a-e, and 7a-e) were tested toward α-Gly and AChE enzymes. Compounds 5a-e, 6a-e, and 7a-e showed Kis in ranging of 341.36 ± 31.84–904.76 ± 93.56?nM on AChE and 176.27 ± 22.87—621.77 ± 69.98?nM on α-glycosidase. Finally, novel compounds were found using molecular docking method to calculate the biological activity of these bases against many enzymes. The enzymes used in these calculations are acetylcholinesterase and α-glycosidase, respectively. Molecule 6b is more effective and active than other molecules with a docking score parameter value of ? 8.77 against AChE enzyme and 6d is more effective and active than other molecules with a docking score parameter value of ? 4.94 against α-Gly enzyme. After calculating the biological activities of novel compounds, ADME/T analysis parameters were examined to calculate the future drug use properties.

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.

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.

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.

Phenoxyacetohydrazones against Trypanosoma cruzi

Herein, we reported the design, synthesis, antitrypanosomal and cytotoxic evaluation of a new phenoxyacetohydrazones series. All derivatives were assayed against bloodstream trypomastigote forms of T. cruzi (Y strain) and intracellular amastigotes using the model of L-929 cells infected with trypomastigotes of the Tulahuen strain. Compound (E)-N′-(3.4-dihydroxybenzylidene)-2-phenoxyacetohydrazide (11) showed activity against trypomastigotes (IC50/24 h = 10.3 μM) equivalent to that of benznidazole and with selectivity index (SI) = 46. Against infected cultures, (E)-N′-((5-nitrofuran-2-yl) methylene)-2-phenoxyacetohydrazide (19) was active at the nanomolar range (IC50/96 h = 40 nM), being about 38-fold more active than the standard drug and with SI equal to 2500. Thus, derivatives 11 and 19 could be considered a good prototypes for the development of new candidates for Chagas disease therapy. [Figure not available: see fulltext.]

Identification of a Novel Oxadiazole Inhibitor of Mammalian Target of Rapamycin

We performed a biochemical screen against mTOR using in-house small molecule library. Two novel, structurally distinct hits were identified. Among them, a novel oxadiazole scaffold compound (2) suppressed the phosphorylation of both S6K1 and Akt1 in HeLa cells. Docking study suggested that 2 is ATP-competitive and shows a pi-pi interaction with Trp2239 and hydrogen bonds with Trp2239 and Thr2245. Through derivatization, a slightly more potent analogue (2a) was identified with IC50 of 9.6 μM. Our study provides a starting point for discovery of novel potent mTOR inhibitors.

Host-guest complexation between simple pillar[5]arene and a new type of neutral guests

Pillar[5]arenes are a new type of supramolecular hosts constructed from hydroquinone and their derivatives linked by methylene units. Searching new host-guest interaction between pillar[5]arenes and neutral guests are thus great interesting. Here, four neutral guests (AA0, AA2, AA4 and AA6) with both amino and amide groups were prepared from phenol by two steps. The host-guest interactions between perethylated pillar[5]arene (EtP5) and guest molecules were investigated in detail by various technologies, including 1H NMR, 13C NMR, 2D NOESY NMR, MS analysis and DFT calculation. We found that the guests (AA4 and AA6) with longer alkyl chain can form a stable inclusion complex with EtP5 through C–H···O, N–H···O, C–H···N and C–H···π interactions while shorter guests (AA0 and AA2) could not.

Synthesis and anti-coronavirus activity of a series of 1-thia-4-azaspiro[4.5]decan-3-one derivatives

A series of 1-thia-4-azaspiro[4.5]decan-3-ones bearing an amide group at C-4 and various substitutions at C-2 and C-8 were synthesized and evaluated against human coronavirus and influenza virus. Compounds 7m, 7n, 8k, 8l, 8m, 8n, and 8p were found to inhibit human coronavirus 229E replication. The most active compound was N-(2-methyl-8-tert-butyl-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl)-3-phenylpropanamide (8n), with an EC50 value of 5.5 μM, comparable to the known coronavirus inhibitor, (Z)-N-[3-[4-(4-bromophenyl)-4-hydroxypiperidin-1-yl]-3-oxo-1-phenylprop-1-en-2-yl]benzamide (K22). Compound 8n and structural analogs were devoid of anti-influenza virus activity, although their scaffold is shared with a previously discovered class of H3 hemagglutinin-specific influenza virus fusion inhibitors. These findings point to the 1-thia-4-azaspiro[4.5]decan-3-one scaffold as a versatile chemical structure with high relevance for antiviral drug development.