66751-87-9

Usage

Uses

Used in Pharmaceutical Research:
(3Z)-3-[2-(4-chlorophenyl)-2-oxoethylidene]-3,4-dihydroquinoxalin-2(1H)-one is used as a research compound for exploring its potential medicinal uses and therapeutic effects due to its structural and functional properties.
Used in Drug Development:
(3Z)-3-[2-(4-chlorophenyl)-2-oxoethylidene]-3,4-dihydroquinoxalin-2(1H)-one is utilized as a starting point for developing new drugs, particularly in the areas of antimicrobial and anticancer therapies, given its demonstrated biological activities.
Further studies may be required to fully understand the compound's potential applications and optimize its use in the medical field.

Upstream product

• 35998-44-8 4-(4-chlorobenzoyl)-3-hydroxy-2(5H)-furanone 
• 95-54-5 1,2-diamino-benzene 
• 85051-44-1 N-p-nitrophenyl-N-α-styrylbenzoylpyruvamide 
• 58303-62-1 5-(4-chlorophenyl)-2,3-dihydrofuran-2,3-dione 
• 65356-49-2 ethyl 4-(4-chlorophenyl)-2-hydroxy-4-oxobut-2-enoate 
• 133880-36-1 [5-(4-Chloro-phenyl)-2-hydroxy-3-oxo-2,3-dihydro-furan-2-yl]-acetic acid methyl ester 
• 159107-87-6 [5-(4-Chloro-phenyl)-2-hydroxy-3-oxo-2,3-dihydro-furan-2-yl]-acetic acid ethyl ester 
• 5814-38-0 ethyl 4-chlorobenzoylpyruvate 
• 39757-35-2 methyl 4-(4-chlorophenyl)-2,4-dioxobutanoate 
• 38053-20-2 4-(4-chlorophenyl)-2,4-dioxobutanoic acid 
• 99-91-2 para-chloroacetophenone 

Downstream Products

• 1187954-78-4 3-(p-chlorophenyl)-1'(H)-spiro[2-pyrazoline-5,2'-quinoxalin]-3'(4'H)-one 
• 1266618-88-5 3-(p-chlorophenyl)-1-phenyl-1'(H)-spiro[2-pyrazoline-5,2'-quinoxalin]-3'(4'H)-one 
• 1187954-82-0 2-[5-(p-chlorophenyl)-1H-pyrazol-3-yl]-1H-benzimidazole 
• 1289383-46-5 3-(4-chlorobenzoyl)pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-trione 
• 1289383-58-9 3-(4-chlorobenzoyl)furo[3,2-b]quinoxalin-2(4H)-one 

Relevant academic research and scientific papers

Interaction of 5-aryl-2,3-dihydrofuran-2,3-diones with functionally substituted hydrazides and diaminoglyoxal diphenylhydrazone

The reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with cyanoacetylhydrazide, o-(hydrazinocarbonyl)phenylthiourea, and the diphenylhydrazone of diaminoglyoxal leads to the synthesis of the corresponding N-cyanoacetylhydrazides of aroylpyruvic acids, 2-(N-

Microwave-assisted one-pot efficient synthesis of functionalized 2-oxo-2-phenylethylidenes-linked 2-oxobenzo[1, 4]oxazines and 2-oxoquino[1, 4]oxalines: Synthetic applications, antioxidant activity, SAR and cytotoxic studies

A microwave-assisted, environmentally benign green protocol for the synthesis of functionalized (Z)-3-(2-oxo-2-phenylethylidene)-3, 4-dihydro-2H-benzo[b][1, 4]oxazin-2-ones (11a-n) in excellent yields (upto 97%) and (Z)-3-(2-oxo-2-phenylethylidene)-3, 4-dihydroquinoxalin-2(1H)-ones (14a-h) (upto 96% yield) are reported. The practical applicability of developed methodology were also confirmed by the gram scale synthesis of 11a, 14c and 14e; synthesis of anticancer alkaloid Cephalandole A 16 (89% yield). All the synthesized compounds 11a-n, 14a-h and 16 were assessed for their in vitro antioxidant activities in DPPH radical scavenging and FRAP assay. In DPPH assay, compounds 11a, 14c and 14e, the most active compounds of the series, were found to show IC50 value of 10.20 ± 0.08 μg/mL, 9.89 ± 0.15 μg/mL and 8.97 ± 0.13 μg/mL, respectively in comparison with standard reference (ascorbic acid, IC50 = 4.57 μg/mL). Whereas, in FRAP antioxidant assay seven compounds (11c, 11e, 11i, 11k, 11l, 14d and 14h) displayed higher antioxidant activity in comparison to the reference standard BHT (C0.5FRAP = 546.2 μM). Moreover, the cytotoxic studies of the compounds 11a, 14c, 14e and 14h were found to be non-toxic in nature in 3T3 fibroblast cell lines using MTT assay.

The effect of substituents on the response of 3,4-dihydro-3-(2-oxo-2- phenylethylidene)-quinoxalin-2(1H)-one derivatives toward binding of Cu 2+

A new series of fluorogenic chelating reagents based on phenylethylidene-3,4-dihydro-1H-quinoxalin-2-one with different substituents (attached either to the quinoxaline-2-one (3) or phenyl ring (4)) have been investigated to examine the effect of the substituent (nature/position) on the spectral properties and response toward Cu2+ in the presence of other metal cations, in ethanol. It was found that all of the examined ligands exhibit a pronounced response to Cu2+ addition resulting in a red-shift in the UV-vis spectra and a strong quenching in the fluorescence spectra. Among the ligands examined, 3a exhibits the highest selectivity toward various metal cations. In general it appears that the best response selectivity of these ligands toward Cu2+ ion is obtained by either EDG in 3 or EWG in 4. For example, the fluorescence intensity of 3a (with OMe substituent) increases to about three times that of the unsubstituted derivative.

Five-membered 2,3-dioxoheterocycles: LXXIII. Synthesis and thermolysis of 3-acylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones

Reactions of (Z)-3-(phenacylidene-2-oxo)-3,4-dihydroquinoxalin-2(1H)-ones and (Z)-3-(3,3-dimethyl-2-oxobutylidene)-3,4-dihydroquinoxalin-2(1H)-one with oxalyl chloride led to the formation of 3-acyl-1Hpyrrolo[1,2-a]quinoxaline-1,2, 4(5H)-triones that at the thermal decarbonylation generated acyl(3- oxoquinoxalin-2-yl)ketenes which underwent the intramolecular stabilization giving 3-acylfuro[3,2-b]quinoxalin-2(4H)-ones.

Five-membered 2,3-dioxo heterocycles: LXVI. Reactions of (2Z,5Z)-1-aryl-3-hydroxy-5-[3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-ylidene] pent-2-ene-1,4-diones with o-phenylenediamine and hydrazine. Crystalline and molecular structure of 2-{(Z)-8,8-dimethyl

(2Z,5Z)-1-Aryl-3-hydroxy-5-[3,3-dimethyl-3,4-dihydroisoquinolin-1(2H) -ylidene]pent-2-ene-1,4-diones reacted with o-phenylenediamine and hydrazine to give 3-[(Z)-2-aryl-2-oxoethylidene]-1,2,3,4-tetrahydroquinoxalin-2-ones and 1-(3-aryl-1H-pyrazol-5-yl)-2-

Sulfamic acid as an effective catalyst in solvent-free synthesis of β-enaminoketone derivatives and X-ray crystallography of their representatives

Two types of β-enaminoketone derivatives of 3-(2-oxo-2-arylethylidene) -3,4-dihydro-1H-quinoxalin-2-ones and 3-(2-oxo-2-arylethylidene)-3,4-dihydro- benzo[1,4]oxazin-2- ones were effectively and conveniently prepared in good to excellent yields under solv

Five-Membered 2,3-Dioxo Heterocycles. XXXIX. Reaction of 4-Aroyl-1-aryl-5-methoxycarbonyl- and 1-Aryl-4-isopropyloxalo-5-phenyl-2,3-dihydropyrrole-2,3-diones with o-Phenylenediamine

4-Aroyl-1-aryl-5-methoxycarbonyl- and 1-aryl-4-isopropyloxalo-5-phenyl-2,3-dihydropyrrole-2,3-diones react with p-phenylenediamine to give substituted 1,2,3,5,10,10a-hexahydropyrrolobenzodiazepine-2,3-diones.Hydrolysis of the latter yields 3-phenacylidene-1,2,3,4-tetrahydroquinoxalin-2-ones.

FIVE-MEMBERED 2,3-DIOXOHETEROCYCLES. XXXV. REACTION OF 5-ARYL-2,3-DIHYDRO-2,3-FURANDIONES WITH KETENE ACETALS. SYNTHESIS, STRUCTURE, AND HETEROCYCLIZATION REACTIONS OF ALKYL 5-ARYL-2-HYDROXY-3-OXO-2,3-DIHYDRO-2-FURYLACETATES

Depending on the nature of the substituent in the benzene ring, in the crystalline state the products from the reaction of 5-aryl-2,3-dihydro-2,3-furandiones with ketene acetals exist in the form of either alkyl 5-aryl-2-hydroxy-3-oxo-2,3-dihydro-2-furyla

Substituted γ-Lactones. XXX (1). Reactions of α-Keto-β-Substituted-γ-butyrolactones with Diamines

The condensation reaction between α-keto-β-aroyl (or acyl)-γ-butyrolactones, 4a-4e and o-phenylenediamine or 2,3-diaminonaphthalene leads under retrograde aldol condensation involving loss of formaldehyde to formation of 3-substituted-3,4-dihydro-2(1H)quinoxalinones or benzoquinoxalinones, 7a-7g, respectively as a new convenient synthesis of this type of heterocyclic systems.The reaction of type 4 compound with 4,5-diaminopyrimidine, 8, was found to proceed differently. 2--4-oxo-3-(hydroxymethyl)-4-phenyl-2-butenoic acid 9 was the only product formed when the reaction between 4a and 8 was run in ethanol.The same reaction in glacial acetic acid proceeds with loss of formaldehyde, to afford 7-phenacylidene-7,8-dihydro-6(1H)-pteridinone 10.The reaction between type 4 compounds and ethylenediamine or 1,4-phenylenediamine leads to the formation of the bis-condensation products 13-15, respectively.

CHEMISTRY OF OXALYL DERIVATIVES OF METHYL KETONES. XXVI. REACTION OF 5-ARYL-2,3-DIHYDRO-2,3-FURANDIONES WITH SCHIFF BASES

5-Aryl-2,3-dihydro-2,3-furanediones react with Schiff bases formed by aromatic aldehydes to give 3-substituted 2,6-diaryl-2,3-dihydro-4H-1,3-oxazin-4-ones.The Schiff bases obtained from acetophenone open ring of 5-aryl-2,3-dihydro-2,3-furanediones, forming N-aryl-Nα-styrylaroylpyruvamides.