Cyclocondensation reaction of heterocyclic carbonyl compounds, Part XIII: Synthesis and cytotoxic activity of some 3,7-diaryl-5-(3,4,5-trimethoxyphenyl)pyrazolo[4,3-e][1,2,4]triazines

Gucký, Tomáš; Fryšová, Iveta; Slouka, Jan; Hajdúch, Marián; Džubák, Petr

doi:10.1016/j.ejmech.2008.05.026

Cited by 43 publications

(26 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…17 Furthermore, 1,2,4-triazine derivatives exhibited comparable antibacterial potencies in vitro as that of ampicillin, 18 and significant broad cytotoxic activity against cancer cell in low micromolar range. 19 Based on these findings, it was of interest to introduce a new series of quinoline and its fused systems incorporated with the above biologically active moieties, especially 1,2,4-triazine, for the evaluation of their antimicrobial and antitumor properties.…”

Section: Introductionmentioning

confidence: 99%

Novel Heterocyclic Derivatives of 2-Quinolinone Associated with Antibacterial and Antitumor Potencies

Hassanin¹,

El-Edfawy²

2012

HETEROCYCLES

View full text Add to dashboard Cite

3-(2,2-Dichloroacetyl)-4-hydroxy-1-methylquinolin-2(1H)-one (2) was utilized to obtain several new quinolinones bearing imidazole, quinoxaline, 1,2,4-triazine, pyridotriazine and triazolotriazine heterocycles as substituents at position 3. Condensation of compound 2 with aminotriazine 11 afforded the iminone 12 which was subjected to annellation reactions leading to some new quinolinones fused at face [c]; viz. pyrazole, pyrimidine and benzodiazepine. Structure of the new compounds was confirmed by spectral and elemental analyses. The synthesized compounds were screened in vitro for their antimicrobial and antitumor activities. Scheme 2 Condensation of compound 2 with 1,4-N,N-binucleophiles such as o-phenylenediamine and 1,6-diaminopyridine derivative 5, 22 under reflux in DMF, afforded the quinoxalinylquinolinone 4 and the

show abstract

Section: Introductionmentioning

confidence: 99%

Novel Heterocyclic Derivatives of 2-Quinolinone Associated with Antibacterial and Antitumor Potencies

Hassanin¹,

El-Edfawy²

2012

HETEROCYCLES

View full text Add to dashboard Cite

show abstract

“…The action of hydrazine hydrate on different oxazolones in different conditions was previously studied , but the stereochemistry of the product obtained was not discussed. Thus, treatment of 1 with hydrazine hydrate in refluxing ethanol afforded the E ‐ configurated isomer hydrazide derivative ( E ) 3a (low yield).…”

Section: Resultsmentioning

confidence: 99%

Action of Some Nitrogen and Carbon Nucleophils on 4‐Arylidene‐1,3‐oxazolones

Youssef

Kandeel

Abou‐Elmagd

et al. 2015

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

1,3‐Oxazolones 1 and 2 were reacted with hydrazine hydrate to afford the corresponding hydrazides 3 and 4. Treatment of the hydrazides withacetylacetone, acetonylacetone, ethyl acetoacetate and diethyl malonateyielded different heterocycles. However, oxazolones 1 and 2 reacted with methyl p‐aminobenzoate to afford the imidazolones 5a,5b which were converted into the hydrazide 3a or the triazinone derivative 6 upon treating with hydrazine hydrate. The structures of the newly synthesized compounds were established using IR, 1H‐NMR, EIMS, and elemental analyses.

show abstract

“…The acid hydrazide derivatives 2 were previously prepared by our research group upon hydrazinolysis of 4‐arylmethylene‐2‐phenyl‐1,3‐oxazole‐5(4 H )‐one 1 . Treatment of the acid hydrazide derivatives 2 with diethyl acetylene‐ dicarboxylate gave the imidazolone derivatives 3 and 4 (cf.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Heterocycles Derived from 4‐Arylmethylene‐2‐phenyl‐1,3‐oxazole‐5(4H)‐ones

Youssef

Kandeel

Abou‐Elmagd

et al. 2015

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

The acid hydrazide derivatives 2 were converted into pyrazolone, triazinone, and schiff bases. However, the reaction of Schiff base 12 with malononitrile or thioglycolic acid gives the pyrazolotriazinone or thiazolidinone derivative, respectively. The structures of the newly synthesized compounds were established on the basis of IR, 1H‐NMR, mass spectral data, and elemental analyses. The antimicrobial activities of the synthesized compounds were examined against two types of bacteria and two types of fungi. Some of the tested compounds showed promising activities.

show abstract

Cyclocondensation reaction of heterocyclic carbonyl compounds, Part XIII: Synthesis and cytotoxic activity of some 3,7-diaryl-5-(3,4,5-trimethoxyphenyl)pyrazolo[4,3-e][1,2,4]triazines

Cited by 43 publications

References 21 publications

Novel Heterocyclic Derivatives of 2-Quinolinone Associated with Antibacterial and Antitumor Potencies

Novel Heterocyclic Derivatives of 2-Quinolinone Associated with Antibacterial and Antitumor Potencies

Action of Some Nitrogen and Carbon Nucleophils on 4‐Arylidene‐1,3‐oxazolones

Synthesis of Novel Heterocycles Derived from 4‐Arylmethylene‐2‐phenyl‐1,3‐oxazole‐5(4H)‐ones

Contact Info

Product

Resources

About