Synthesis and anti-tumor activities of new [1,2,4]triazolo[1,5-a]pyrimidine derivatives

Ahmed, Sayed A.; Ahmed, Osama M.; Abdelhamid, Abdou O.

doi:10.5155/eurjchem.5.2.334-338.910

Cited by 10 publications

(4 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Similarly, the 2-cyano- N -(1-substituted ethylidene)acetohydrazides 3a–d reacted with the appropriate sodium (2‐oxocyclopentylidene)methanolate ( 11a ) [32] or sodium 2‐oxocyclohexylidene)methanolate ( 11b ) [32] in acetic acid containing piperidine acetate to give 2-oxo-1-((1-aryl(heteryl)ethylidene)amino)-1 H -cycloalkana[b]pyridine-3-carbonitrile derivatives 13a–h , respectively (Scheme 3). The structure of 13a–d has been assigned as a reaction product on the basis of analytical and spectral data.…”

Section: Resultsmentioning

confidence: 99%

Facile synthesis and antiproliferative activity of new 3-cyanopyridines

et al. 2019

View full text Add to dashboard Cite

BackgroundPyridines have been reported to possess various pharmacological activities.ResultsSodium 3-oxo-3-(2-oxo-2H-chromen-3-yl)prop-1-en-1-olate (2) and sodium 3-oxo-3-(3-oxo-3H-benzo[f]chromen-2-yl)prop-1-en-1-olate (7) were prepared and reacted with 2-cyano-N’-(1-aryl(heteryl)ethylidene)acetohydrazides 3a–d to produce 2-oxo-1,2-dihydropyridine-3-carbonitrile derivatives 5a–d and 9a–d, respectively, in good yields. Also, 3a–d reacted with sodium (2-oxocyclopentylidene)methanolate (11a) or sodium (2-oxocyclohexylidene) methanolate (11b) to yield 2-oxo-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitriles 13a–d and 2-oxo-hexahydroquinoline-3-carbonitriles 13e–h, respectively. The mechanisms that account for the formation of the products are discussed. Additionally, the structures of all the newly synthesized products are confirmed, based on elemental analysis and spectral data. Several of the newly synthesized compounds are evaluated for their antitumor activity against HEPG2 and their structure activity relationship (SAR) was studied.ConclusionsThe results revealed that the pyridine derivatives 5c and 5d (IC50 = 1.46, 7.08 µM, respectively) have promising antitumor activity against liver carcinoma cell line (HEPG2), compared to the reference drug, doxorubicin.

show abstract

Section: Resultsmentioning

confidence: 99%

Facile synthesis and antiproliferative activity of new 3-cyanopyridines

et al. 2019

View full text Add to dashboard Cite

show abstract

“…[8][9][10][11][12][13] Encouraged by these reports and in continuation of our interest in the synthesis of a variety of heterocyclic systems as biologically active compounds, [14][15][16][17] we describe here a facile synthesis and structural elucidation of some new [1,2,4]triazolo [3,4-b] pteridine derivatives as a novel heterocyclic system.…”

Section: Cardiovascular Activitiesmentioning

confidence: 96%

“…A number of methods that have been reported for the synthesis of triazolopyrimidinone derivatives involving condensation of 2-hydrazinopyrimidine with ortho esters, oxidative ring closure of the arylmethylene derivatives of 2-hydrazinopyrimidines, condensation of 3-amino-1,2,4-triazoles with 1,3-dicarbonyl compounds, reaction of aminotriazole, carbonyl compounds and alkene-nitrile derivatives in aqueous medium and condensation of 1H-1,2,4-triazol-5-amine with the appropriate sodium 2-oxocycloalkylidene)methanolate. [8][9][10][11][12][13] Encouraged by these reports and in continuation of our interest in the synthesis of a variety of heterocyclic systems as biologically active compounds, [14][15][16][17] we describe here a facile synthesis and structural elucidation of some new [1,2,4]triazolo [3,4-b] pteridine derivatives as a novel heterocyclic system.…”

Section: Cardiovascular Activitiesmentioning

confidence: 96%

Synthesis of [1,2,4]Triazolo[3,4-b]Pteridines as a Novel Class of Heterocyclic Compounds

Mokaber-Esfahani

Shiri

Akbarzadeh

et al. 2015

Journal of Chemical Research

View full text Add to dashboard Cite

ConclusionsIn conclusion, we have elaborated a general approach to an efficient and selective intramolecular coupling of the amines derived amino acid esters with chloro-substituted pyrimidine. VOL. 39 APRIL, 216-219Synthesis of [1,2,4]triazolo [3,4-b]pteridines as a novel class of heterocyclic compounds † A series of pteridine derivatives have been synthesised through intramolecular cyclisation of 2,4-dichloro-6-methyl-5-nitro pyrimidine with various esters of amino acids. The subsequently reaction of pteridines with hydrazine hydrate and then with triethylorthoesters obtained quantitatively the desired [1,2,4]triazolo[3,4-b]pteridine derivatives as a novel heterocyclic system.

show abstract

“…In addition, daphnetin inhibits tyrosine kinase, epidermal growth factor receptor, serine/threonine-specific protein kinase, and protein kinase C in vitro [17]. On the other hand, thiazole [18], 1,3,4-thiadiazole [19], azolo[1,5- a ]pyrimidine [20], coumarin [21] derivatives displayed significant antitumor, cytotoxic, antiinflammatory, anticoagulant, antioxidant, antifungal, antitubercular, anticonvulsant, antimicrobial, antiviral, neuroprotective and diuretic activities. In continuation of our research program on the synthesis of novel heterocyclic compounds exhibiting antitumor activities [22,23,24,25,26], we attempted to design pyrazolo[1,5- a ]pyrimidine, tetrazolo[1,5- a ]-pyrimidine, imidazo[1,2- a ]pyrimidine, pyrazolo[3,4- d ]pyridazine, thiazoles, and thiadiazoles linked to position 3 of coumarin as a novel 3-heteroarylcoumarins, which have not been reported hitherto, to evaluate their in vitro antitumor activity against a liver carcinoma cell line (HEPG2-1).…”

Section: Introductionmentioning

confidence: 99%

Utility of 3-Acetyl-6-bromo-2H-chromen-2-one for the Synthesis of New Heterocycles as Potential Antiproliferative Agents

2015

View full text Add to dashboard Cite

Abstract:Coumarin derivatives containing pyrazolo [1,5-a]pyrimidine, tetrazolo [1,5-a]pyrimidine, imidazo[1,2-a]pyrimidine, pyrazolo [3,4-d]pyrimidine, 1,3,4-thiadiazoles and thiazoles were synthesized from 6-bromo-3-(3-(dimethylamino)acryloyl)-2H-chromen-2-one, methyl 2-(1-(6-bromo-2-oxo-2H-chromen-3-yl)ethylidene)hydrazine carbodithioate, 2-(1-(6-bromo-2-oxo-2H-chromen-3-yl)ethylidene) hydrazine carbothioamide and each of heterocyclic amine, hydrazonoyl chlorides and hydroximoyl chlorides. The structures of the newly synthesized compounds were elucidated on the basis of elemental analysis, spectral data, and alternative synthetic routes whenever possible. Moreover, selected newly synthesized products were evaluated for their antitumor activity against a liver carcinoma cancer cell line (HEPG2-1). The results revealed that pyrazolo[1,5-a]pyrimidine 7c, thiazole 23g and 1,3,4-thiadiazole 18a (IC50 = 2.70 ± 0.28, 3.50 ± 0.23 and 4.90 ± 0.69 µM, respectively) have promising antitumor activity against liver carcinoma (HEPG2-1) while most of the tested compounds showed moderate activity.

show abstract

Synthesis and anti-tumor activities of new [1,2,4]triazolo[1,5-a]pyrimidine derivatives

Cited by 10 publications

References 13 publications

Facile synthesis and antiproliferative activity of new 3-cyanopyridines

Facile synthesis and antiproliferative activity of new 3-cyanopyridines

Synthesis of [1,2,4]Triazolo[3,4-b]Pteridines as a Novel Class of Heterocyclic Compounds

Utility of 3-Acetyl-6-bromo-2H-chromen-2-one for the Synthesis of New Heterocycles as Potential Antiproliferative Agents

Contact Info

Product

Resources

About