5429-22-1

Basic information

• Product Name: 4-(4-METHOXYBENZYLIDENE)-2-PHENYL-2-OXAZOLIN-5-ONE
• Synonyms: (4E)-4-[(4-methoxyphenyl)methylidene]-2-phenyl-1,3-oxazol-5-one
• CAS NO: 5429-22-1
• Molecular Formula: C₁₇H₁₃NO₃
• Molecular Weight: 279.2981
• Mol File: 5429-22-1.mol

Chemical Properties

• Melting Point: 160 °C
• Boiling Point: 434.8°Cat760mmHg
• Flash Point: 196.2°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 9.2E-08mmHg at 25°C
• Refractive Index: 1.594
• PKA: -0.18±0.20(Predicted)
• CAS DataBase Reference: 4-(4-METHOXYBENZYLIDENE)-2-PHENYL-2-OXAZOLIN-5-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-METHOXYBENZYLIDENE)-2-PHENYL-2-OXAZOLIN-5-ONE(5429-22-1)
• EPA Substance Registry System: 4-(4-METHOXYBENZYLIDENE)-2-PHENYL-2-OXAZOLIN-5-ONE(5429-22-1)

Safety Data

• Hazardous Substances Data: 5429-22-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-(4-Methoxybenzylidene)-2-phenyl-2-oxazolin-5-one is used as a reagent in organic synthesis for the production of complex organic molecules. Its chemical reactivity and structural characteristics make it a valuable building block in the synthesis process.
Used in Pharmaceutical Industry:
4-(4-Methoxybenzylidene)-2-phenyl-2-oxazolin-5-one is used in the pharmaceutical industry for the production of various drugs. Its potential biological and medicinal properties, including antimicrobial, antifungal, and anticancer activities, make it a promising candidate for drug development.
Used in Antimicrobial Applications:
4-(4-Methoxybenzylidene)-2-phenyl-2-oxazolin-5-one is used as an antimicrobial agent, exhibiting activity against various types of bacteria. Its potential to inhibit bacterial growth makes it a useful compound in the development of new antimicrobial drugs.
Used in Antifungal Applications:
4-(4-Methoxybenzylidene)-2-phenyl-2-oxazolin-5-one is used as an antifungal agent, showing activity against various types of fungi. Its potential to inhibit fungal growth makes it a useful compound in the development of new antifungal drugs.
Used in Anticancer Applications:
4-(4-Methoxybenzylidene)-2-pheny

InChI:InChI=1/C17H13NO3/c1-20-14-9-7-12(8-10-14)11-15-17(19)21-16(18-15)13-5-3-2-4-6-13/h2-11H,1H3/b15-11+

Upstream product

• 495-69-2 Hippuric Acid 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 123-11-5 4-methoxy-benzaldehyde 
• 19746-91-9 4-(4-methoxyphenylmethylene)-6-phenyl-3H-1,3,5-oxadiazin-2-one 
• 1199-01-5 2-phenylazlactone 
• 211808-98-9 3-(ethoxycarbonyl)benzotriazol-1-oxide 
• 33402-67-4 sodium hydroxy(4-methoxyphenyl)methanesulfonate 
• 2826-26-8 2-(4-methoxyphenylmethylene)malononitrile 
• 65-85-0 benzoic acid 
• 4231-62-3 1-benzoyl-1H-benzotriazole 
• 532-94-5 sodium hippurate 
• 105-13-5 4-Methoxybenzyl alcohol 
• 98-88-4 benzoyl chloride 

Downstream Products

• 18510-78-6 4-(4-methoxy-benzylidene)-2,6-diphenyl-4H-[1,2,5]oxadiazin-3-one 
• 103271-58-5 4-(4-methoxy-benzylidene)-5,5-bis-(4-methoxy-phenyl)-2-phenyl-4,5-dihydro-oxazole 
• 96505-21-4 4-(4-methoxy-benzhydryl)-2-phenyl-4H-oxazol-5-one 
• 4491-58-1 3'-(4-methoxy-phenyl)-2''-phenyl-dispiro[fluorene-9,1'-cyclopropane-2',4''-oxazol]-5''-one 
• 904-42-7 4-(4-methoxy-3-nitro-benzylidene)-2-phenyl-4H-oxazol-5-one 
• 57427-93-7 2-phenyl-4-<α-E-p-methoxyphenylethylidene>-5(4H)-oxazolone 
• 15427-02-8 1t-(4-methoxy-phenyl)-5-phenyl-(3rN)-6-oxa-4-aza-spiro[2.4]hept-4-en-7-one 
• 15427-02-8 (1S,3S)-1-(4-Methoxy-phenyl)-5-phenyl-6-oxa-4-aza-spiro[2.4]hept-4-en-7-one 
• 109876-83-7 7-(p-methoxyphenyl)-2,5-diphenyloxazolo<5,4-b>pyridine 
• 130087-68-2 N-[7-(4-Methoxy-phenyl)-5-oxo-3-m-tolyl-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3]thiazin-6-yl]-benzamide 
• 130087-71-7 N-[3-(4-Chloro-phenoxymethyl)-7-(4-methoxy-phenyl)-5-oxo-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3]thiazin-6-yl]-benzamide 
• 130087-74-0 N-[3-(2,4-Dichloro-phenoxymethyl)-7-(4-methoxy-phenyl)-5-oxo-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3]thiazin-6-yl]-benzamide 
• 141421-11-6 7-(4-Methoxy-phenyl)-2-phenyl-5-p-tolyl-oxazolo[5,4-b]pyridine 
• 28030-16-2 3-(4-methoxyphenyl)-2-oxopropanoic acid 

Relevant articles and documents

Synthesis, characterization, swelling and antimicrobial efficacies of chemically modified chitosan biopolymer

Three heterocyclic compounds namely: (Z)-4-benzylidene-2-phenyl-1,3-oxazol-5-one (A), (Z)-4-(4-methoxybenzylidene)-2-phenyl-1,3-oxazol-5-one (B), (Z)-4-(2-thienyl methylene)-2-phenyl-1,3-oxazol-5-one (C) were prepared in one step reaction between hippuric

Zeolite (Y-H)-based green synthesis, antimicrobial activity, and molecular docking studies of imidazole bearing oxydibenzene hybrid molecules

In this green synthesis, zeolite (Y-H) appears to be an intriguing choice for obtaining a high yield with a shorter reaction time. In addition, we have synthesized N-aryl-(4-benzylidene-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-3-phenoxybenzamides (4a-i), which will be proved to be potent antimicrobial agents. The title compounds were tested against Gram-positive, Gram-negative, and fungal strains using the Mueller–Hinton Broth technique. N-(4-benzylidene-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-3-phenoxybenzamide (4a) (minimum inhibitory concentration [MIC]?=?25 μg/mL, S. pyogenes) and N-(4-[4-fluorobenzylidene]-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-3-phenoxybenzamide (4f) (MIC?=?100 μg/mL, C. albicans, A. niger, A. clavatus) were the most effective against Gram-positive and Gram-negative bacteria as well as fungal strains. To understand the mechanism of action of synthesized compounds, molecular docking experiments were performed against S. aureus tyrosyl-tRNA synthetase and C. albicans sterol 14-α demethylase.

Novel Approach to the Synthesis of 3-amino-4-arylpyridin-2(1H)-one Derivatives

[Figure not available: see fulltext.] The reaction of 4-arylidene-2-phenyloxazol-5(4H)-ones with enamines of ethyl acetoacetate gave 4-aryl-2-methyl-6-oxo-5-[(phenylcarbonyl)amino]-1,4,5,6-tetrahydropyridine-3-carboxylic acid esters, which, when heated with phosphorus oxychloride, were converted into esters of 7-aryl-5-methyl-2-phenyloxazolo[5,4-b]pyridine-6-carboxylic acids. Alkaline hydrolysis of these compounds gave 4-aryl-2-methyl-6-oxo-5-[(phenylcarbonyl)amino]-1,6-dihydropyridine-3-carboxylic acid esters.

Design, Synthesis, and Antimicrobial Activity of Novel Fluorine-Containing Imidazolones

Abstract: A simple synthetic protocol have been developed for the preparation of novelN-(4-benzylidene-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-N′-phenylthiourea derivatives by the reaction of4-benzylidene-2-phenyl-4,5-dihydro-1,3-oxazol-5-ones with N

Synthesis, assessment and corrosion protection investigations of some novel peptidomimetic cationic surfactants: Empirical and theoretical insights

Three novel peptidomimetic cationic surfactants were synthesized in good yields. The chemical configurations of these surfactants were clarified using 1H, 13C NMR and FT-IR spectroscopy. The inhibition capacity and adsorption performance of these compounds on C-steel were studied by electrochemical techniques (Electrochemical impedance spectroscopy (EIS) and Potentiodynamic polarization (PDP) methods). The prepared compounds demonstrated outstanding protection power for the erosion of C-steel in 0.5 M HCl at 323 K. The PDP studies demonstrated that the novel surfactants behaved as mixed-type additives. The protection capacity rises with an increasing surfactant dose, with values ranging from 93.10 to 98.25percent at 100 ppm. The adsorption of additives on the electrode interface follows the Langmuir model and contains chemisorption modes. The Monte Carlo (MD) simulations and density functional theory (DFT) calculations support the experimental findings and provide insight into the understanding of the adsorption features and protection performance mechanisms of the examined surfactants.

Synthesis and pharmacological effects of novel benzenesulfonamides carrying benzamide moiety as carbonic anhydrase and acetylcholinesterase inhibitors

N-(1-(4-Methoxyphenyl)-3-oxo-3-((4-(N-(substituted)sulfamoyl)phenyl)amino)prop-1-en-1-yl)benzamides 3a - g were designed since sulfonamide and benzamide pharmacophores draw great attention in novel drug design due to their wide range of bioactivities including acetylcholinesterase (AChE) and human carbonic anhydrase I and II (hCA I and hCA II) inhibitory potencies. Structure elucidation of the compounds was carried out by 1H NMR, 13C NMR, and HRMS spectra. In vitro enzyme assays showed that the compounds had significant inhibitory potential against hCA I, hCA II, and AChE enzymes at nanomolar levels. Ki values were in the range of 4.07 ± 0.38 - 29.70 ± 3.18 nM for hCA I and 10.68 ± 0.98 - 37.16 ± 7.55 nM for hCA II while Ki values for AChE were in the range of 8.91 ± 1.65 - 34.02 ± 5.90 nM. The most potent inhibitors 3g (Ki = 4.07 ± 0.38 nM, hCA I), 3c (Ki = 10.68 ± 0.98 nM, hCA II), and 3f (Ki = 8.91 ± 1.65 nM, AChE) can be considered as lead compounds of this study with their promising bioactivity results. Secondary sulfonamides showed promising enzyme inhibitory effects on AChE while primary sulfonamide derivative was generally effective on hCA I and hCA II isoenzymes.

Base Induced Condensation of Malononitrile with Erlenmeyer Azlactones: An Unexpected Synthesis of Multi-Substituted Δ2-Pyrrolines and Their Cytotoxicity

An efficient, metal free approach to synthesize multi-substituted Δ2-pyrroline derivatives by mild base catalyzed cyclocondensation of malononitrile with Erlenmeyer azlactones via 1,2 addition was developed. The modularity of this reaction was used to assemble a range of poly-substituted pyrrolines. Further, synthesized products were screened for cytotoxic properties on different cancer cell lines such as A549 (Human lung adenocarcinoma cells), HeLa (Human cervical adenocarcinoma cells), Jurkat (Human chronic myeloid leukemia cells) and K562 (Human leukemic T cell Lymphoblast cells). Among the synthesized library of compounds, 6f and 6q displayed potent cytotoxic activity.

Novel diamide-based benzenesulfonamides as selective carbonic anhydrase ix inhibitors endowed with antitumor activity: Synthesis, biological evaluation and in silico insights

In this work, we present the synthesis and biological evaluation of novel series of diamide-based benzenesulfonamides 5a-h as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I, II, IX and XII. The target tumor-associated i

Benzothiazol clubbed imidazol-4-ones as anti-fungal, anti-tubercular and anti-HIV-1 agents: Their synthesis and molecular docking study

Background: The present work describes antimicrobial, antimycobacterium and anti HIV-1 evaluation of newly synthesized 5-(4-Substituted-benzylidene)-3-[4-(5-methyl-benzothiazol2-yl)-phenyl]-2-phenyl-3,5-dihydro-imidazol-4-one (4a-o). The docking studies were performed in order to predict the potential binding affinities. Objective: The major aim of this study is to develop the new class of bezylidine candidate clubbed with benzothiazole with less toxicity and improved potency as antimicrobial, antitubercular and anti HIV-1. Methods: The titled compounds were characterized by spectral studies (IR, 1H NMR, 13C NMR and Mass). In vitro antimycobacterium activity was carried out using Lowenstein-Jensen medium method and antimicrobial activity using the broth microdilution method. The anti HIV-1 reverse transcriptase activity was determined by the colorimetric MTT method and inhibition of virusinduced cytopathogenicity in MT-4 cells. Results: Compound 4i (50 μM) showed better antifungal activity against A. clavatus. Compound 4g (50 μM) with 95% inhibition demonstrated good activity against M. tuberculosis H37Rv. Compound 4k showed CC50 (50 μM) against MT-4 (CD4+ Human T-cells containing an integrated HTLV-1 genome) cells by 50%, while 16 μM concentration value EC50 from the HIV-1 induced cytopathogenicity. Molecular docking study suggested that 4k interacted with the target with binding energy by Vina score (-10.3 Kcal/mol) Conclusion: The preliminary in vitro evaluation results revealed that some of the compounds have promising antimicrobial activities as well as antitubercular potency. Among the various substituents on benzylidene, the nitro group was the most beneficial for improving the anti-HIV-1 activity. Docking result suggested that 4k compound could be acting as a non-competitive or weak inhibitor of Reverse Transcriptase (RT).

An ionic liquid gel: A heterogeneous catalyst for Erlenmeyer-Plochl and Henry reactions

An ionic liquid gel has been prepared by entrapping 1-butyl-3-methylimidazolium hydroxide ([Bmim]OH) in an aqueous agar gel. The ionic liquid gel has been characterized by Fourier transform infrared (FT-IR), Fourier transform Raman (FT-Raman) spectroscopy, scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). The ionic liquid gel has been successfully employed as a heterogeneous catalyst in the Erlenmeyer-Plochl reaction involving aldehydes, hippuric acid and acetic anhydride as well as in the Henry reaction between aldehydes and nitromethane in ethanol at room temperature. The heterogeneity of the ionic liquid gel has been confirmed by conducting hot filtration tests and leaching studies. Additionally, the ionic liquid gel could be easily recovered by simple filtration and reused five times without significant loss in catalytic activity.