Synthesis and anticonvulsant activity of some quinazolin-4-(3H)-one derivatives

A number of 3-substituted-2-(substituted-phenoxymethyl) quinazolin-4(3H)-one derivatives 4a,b, 5a-c, 6, 7a-f, 8a-e and 9a,b have been synthesized. Their structures have been elucidated on the basis of elemental analyses and spectroscopic studies (IR, 1H-NMR, MS). A preliminary evaluation of the anticonvulsant activity of the prepared compounds has indicated that compounds 4b, 7b-f, 8a and 9b exhibit significant anticonvulsant activity, while compounds 6, 8b and 8d show mild to moderate activity.     

Synthesis and antiproliferative evaluation of some novel quinazolin-4(3H)-one derivatives

A series of novel quinazolinone derivatives was designed and synthesized. The antiproliferative activities were evaluated in vitro using MTT assay against hepatocellular carcinoma (HepG-2) and mammary gland breast cancer (MCF-7). The preliminary bioassay results demonstrated that tested compounds exhibited antiproliferation with various degrees. Triazole moiety enhanced the activity against the two cell lines when incorporating with quinazolinone moiety in a single molecular framework. Acetohydrazide-quinazolinone derivative showed strong activity against the two cancer cells comparable to that of doxorubicin. Biological evaluation indicated that all the tested compounds possessed antiproliferative activity with certain degrees.     

Synthesis of 3-methylquinazolin-4(3H)-one derivatives

Oxidation of 3-methyl-2-sulfanylquinazolin-4(3H)-one with chlorine dioxide under different conditions gave 2,2??-disulfanediylbis[3-methylquinazolin-4(3H)-one], 3-methyl-4-oxo-3,4-dihydroquinazoline-2-sulfonic acid, 3-methylquinazoline-2,4(1H,3H)-dione, 6-chloro-3-methylquinazoline-2,4(1H,3H)-dione, and N,N-diethyl-3-methyl-4-oxo-3,4-dihydroquinazoline-2-sulfonamide.     

Synthesis,anticorrosion, antibacterial,and antifungal activity of new amphiphilic compounds possessing quinazolin-4(3H)-one scaffold

Russian Chemical Bulletin - For the first time, quinazolin-4(3H)-one-based cationic surfactants were prepared and fully characterized by IR and NMR spectroscopic techniques and elemental analysis....     

Synthesis and antimicrobial activity of Schiff bases and 2-azetidinones derived from quinazolin-4(3H)-one

A series of 2-oxo-azetidinyl-quinazolin-4(3H)-ones 5a–k have been synthesized from Schiff bases 4a–k. Schiff bases were synthesized by the condensation reaction of compound 3 with substituted aromatic aldehydes. The benzoxazinone 2 was prepared by the cyclization reaction of acid chloride 1 with 5-bromo anthranilic acid. Further reaction of benzoxazinone 2 with hydrazine hydrate yielded compound 3. The structures of the synthesized compounds were elucidated on the basis of elemental analyses as well as IR and NMR spectral data. Schiff bases 4a–k and 2-azetidinones 5a–k were screened for antibacterial and antifungal activities in vitro. Compounds having chloro and methoxy groups exhibited good antimicrobial activity.     

Synthesis and anticonvulsant activity of 3-amino-4(3H)-quinazolinones

Several 3-amino-4(3H)-quinazolinones were prepared from o-aminobenzoylhydrazines and triethyl orthoformate or from isatoic anhydrides, hydrazines and triethyl orthoformate. o-Aminobenzoylhydrazine intermediates were obtained by reaction of isatoic anhydrides with hydrazines. Some of the aminoquinazolinones displayed anticonvulsant activity in mice.     

Synthesis of N-methylpiperidin-4-one derivatives and evaluation of their anti-endometrial cancer activity

Russian Journal of General Chemistry - Four novel N-methylpiperidin-4-one derivatives were synthesized and characterized by IR, 1H NMR, HRMS, and single crystal X-ray crystallography. The...     

One-pot synthesis of 3-(2-cyanophenyl)quinazolin-4(3H)-one

Anthranilonitrile reacting with formic acid at room temperature for three days gave 64% of 3-(2-cyanophenyl)quinazolin-4(3H)-one. Under similar conditions anthranilic acid. 4-nitroaniline, and 2,5-dichloroaniline were N-formylated in good yields.Institute of Organic Chemistry and Technology, Silesian Technical University, Krzywoustego, 4, 44–100 Gliwice, Poland; e-mail: wojtex@zeus.polsl.gliwice.pl. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 922–924, July, 2000.     

Synthesis and antioxidant activity of some thiazolidin-4-one derivatives

Abstract  4-Fluorobenzaldehyde was used for the preparation of 2-(4-fluorophenyl)thiazolidin-4-one derivatives which were allowed to react with chloroacetonitrile and acrylonitrile to produce 3-(2-(4-fluorophenyl)-4-oxothiazolidine3-yl)acetonitrile and 3-(2-(4-fluorophenyl)-4-oxothiazoledine-3-yl)propanenitrile. Biological evaluation of some of the compounds showed that many had promising antioxidant activity. Graphical Abstract        

Synthesis of new 4-(pyrimidin-4-yl)pyrazol-3-one derivatives

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Synthesis of some 5-arylidene-2-(4-acetamidophenylimino)-thiazolidin-4-one derivatives and exploring their breast anticancer activity

Ten 2-(4-acetamidophenylimino)-5-arylidenethiazolidin-4-one derivatives 6a-k were synthesized and evaluated for their anticancer activity against MCF-7 cell line (breast adenocarcinoma). The synthetic approach involves cyclocondensation of N,N′-bis(4-acetamidophenyl)-thiourea (3) with ethyl bromoacetate in ethanol and sodium acetate to furnish the 2-(4-acetamidophenylimino)-4-thiazolidinone derivative 4 , which underwent Knoevenagel condensation reaction with some substituted aldehydes to afford the targeted 2-(4-acetamidophenylimino)-5-arylidenethiazolidin-4-ones 6a - k . The 4-chlorobenzylidene-thiazolidin-4-one compound 6h exhibited strong inhibitory effect on the growth of breast cancer cell with IC₅₀ (58.33 ± 1.74μM), very close to that of the reference drug doxorubicin (IC₅₀ 48.06 ± 0.36μM).     

Synthesis,characterization, and biological evaluation of new quinazolin-4-one derivatives hybridized with pyridine or pyran moiety

Research on Chemical Intermediates - A new series of 2-(furan-2-yl)-4-oxoquinazolin-3-phenyl derivatives hybridized with pyridine 3a–d, 4a–d or pyran moiety 5a–d were synthesized;...     

Synthesis,characterization and biological activity of new 3(4H)-quinazolinone derivatives

Russian Journal of General Chemistry - Quinazolinylbenzoic acid 1 was used as a precursor for synthesis of many heterocyclic systems. Ethyl 4-[4-oxo-2-phenylquinazolin-3(4H)-yl]benzoate 2 upon...     

Synthesis and anticonvulsant activity of some new arylidenehydrazides and 4-thiazolidinones

Summary A number of N,N-bis(arylidene)mono(1-methylpropyl)malonic acid dihydrazides (3a–c), 1,1-bis[[(2-aryl-4-thiazolidinone-3-yl)amino]carbonyl]-2-methylbutanes (4a–e), and 1,1-bis[[(3-alkyl/aryl-4-thiazolidinone-2-yl)hydrazono]carbonyl]-2-methylbutanes (6a–i) have been synthesized, characterized and evaluated for anticonvulsant activity. All tested compounds showed significant activity (10 to 60% protection) against pentylenetetrazole induced seizures.

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Synthese einiger neuer Arylidenhydrazide und 4-Thiazolidinone sowie Untersuchung ihrer krampflösenden Eigenschaften

Zusammenfassung Eine Reihe von N,N-Bis(aryliden)mono(1-methylpropyl)malonsäure dihydraziden, (3a–c), 1,1-Bis[[2-Aryl-4-thiazolidinon-3-yl)amino]carbonyl]-2-methylbutanen (4a–e) und 1,1-Bis[[3-alkyl/aryl-4-thiazolidinon-2-yl)hydrazono]carbonyl]-2-methylbutanen (6a–i) wurden hergestellt, charakterisiert und auf ihre antikonvulsive Wirkung geprüft. Alle getesteten Substanzen zeigen relevante Aktivitäten gegen durch Pentilentetrazol induzierte Krämpfe (10–60% Schutz).

     

Synthesis of some new 3-pyrazolyl-substituted-4(3H)quinazolinones

N-(1-Phenyl-3-methylpyrazol-5-yl)-o-aminobenzamide reacted with orthoesters to yield some new 3-pyrazolyl-substituted-4(3H)quinazolinones (VIIa,b,c,d). An alternative synthesis of Vllb was accomplished by reaction of acetylanthranyl with l-phenyl-3-methyl-5-aminopyrazole.     

Synthesis of new 4(3H)-quinazolinone derivatives using 5(4H)-oxazolones

New derivatives of 5(4H)-quinazolinone containing 2-imidazolin-5-one rings have been prepared from 5(4H)-oxazolone derivatives.