Molecular design of pyrazolo[3,4-d]pyridazines

Matiychuk, V. S.; Potopnyk, Mykhaylo A.; Обушак, Н. Д.

doi:10.1134/s1070428008090182

Cited by 36 publications

(29 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Synthesis of pyrimido [3,4-b][1,2,4]triazin-3(4H)-one derivative 27 was achieved by the reaction of 3-amino-4iminopyrimidine derivative [19] 26 with ethyl 2-chloro-2-[2-(4-chlorophenyl)hydrazono]acetate (16b) [30] in refluxing absolute ethanol containing a catalytic drops of triethylamine. [41] The 1 H NMR spectrum of compound 27 displayed four deuterium oxide exchangeable singlet signals at δ 10.69, δ 11.57, and δ 12.98 ppm corresponding to triazine-NH, hydrazone-NH, and tautomeric OH protons, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…The reaction mixture was poured onto ice-cold water, and the separated solid was filtered, washed with water, dried, and crystallized from EtOH/DMF mixture (3:1) to afford chocolate brown crystals. (27) An equimolar mixture of compound 26 [19] (1.54 g, 5 mmol), ethyl 2-chloro-2-[2-(4-chlorophenyl)hydrazono] acetate (16b) [30] (1.31 g, 5 mmol), and triethylamine (0.51 g, 0.70 mL, 5 mmol) was heated under reflux in absolute ethanol (40 mL) for 13 hours. 1 A mixture of compound 18 (0.74 g, 2 mmol) and an equimolar amount of benzohydrazide (20) [37] (0.27 g, 2 mmol) was heated under reflux in pyridine (10 mL) for 24 hours.…”

Section: General Synthetic Procedures For the Preparation Of Compounmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and antitumor evaluation of some new derivatives and fused heterocyclic compounds derived from thieno[2,3‐b]pyridine: Part 2

Hassan

Sarg

El‐Sebaey

2019

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

As a continuation of our research on developing anticancer agents and based on the proven proprieties of thieno[2,3-b]pyridines as anticancer, we have designed to synthesize novel thieno[2,3-b]pyridine derivatives that incorporate different biologically active heterocycles through various chemical reactions.All of the newly obtained compounds, compared with the standard anticancer drug (doxorubicin), were screened in vitro for their antitumor activity against hepatocellular carcinoma (HepG-2) and human breast cancer (MCF-7) cell lines. The results revealed that compounds 3, 7, 12, and 19 were found to be the most potent against both HepG-2 and MCF-7 cell lines exhibiting IC 50 values ranging from 3.67 to 11.50 and 5.13 to 11.80 μg/mL, respectively, among which compound 7 has a more potent activity than the reference drug doxorubicin against HepG-2 cell line, showing IC 50 value of 3.67 μg/mL (doxorubicin 4.65 μg/mL).

show abstract

Section: Resultsmentioning

confidence: 99%

Section: General Synthetic Procedures For the Preparation Of Compounmentioning

confidence: 99%

Synthesis and antitumor evaluation of some new derivatives and fused heterocyclic compounds derived from thieno[2,3‐b]pyridine: Part 2

Hassan

Sarg

El‐Sebaey

2019

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…Ethyl 2‐(arylhydrazono)propanoates 147 reacted with the Vilsmeier–Haack reagent to give ethyl 1‐aryl‐4‐formyl‐1 H ‐pyrazole‐3‐carboxylates 148 . Ethyl 4‐acetyl‐1‐aryl‐5‐methyl‐1 H ‐pyrazole‐3‐carboxylates 149 were obtained by reaction of 147 with acetylacetone (Scheme ) .…”

Section: Synthetic Methodsmentioning

confidence: 99%

Synthetic Routes to Pyrazole‐3(5)‐carboxylates

Khidre

Abdel‐Wahab

Farahat

et al. 2015

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…The mass spectra (chemical ionization) were obtained on an Agilent 1100 LC/MSD instrument. Hydrazones VIIIa-VIIIe were synthesized as described in [11]. …”

Section: Methodsmentioning

confidence: 99%

“…sodium methoxide, and the subsequent hydrolysis gave pyrazolecarboxylic acids IXa-IXe in 54-83% yield (Scheme 3). Taking into account considerable interest in pyrazole derivatives [10], compound І was brought into reaction analogous to the reaction of chlorohydrazones with β-keto esters [11]. Such reactions were performed previously using ethyl acetoacetate [12].…”

mentioning

confidence: 99%

Methyl 3-cyclopropyl-3-oxopropanoate in the synthesis of heterocycles having a cyclopropyl substituent

2010

Self Cite

View full text Add to dashboard Cite

Reactions of methyl 3-cyclopropyl-3-oxopropanoate with chloroacetone and ammonia, benzaldehyde and ammonia, and benzoquinone gave, respectively, methyl 2-cyclopropyl-5-methyl-1H-pyrrole-3-carboxylate, dimethyl 2,6-dicyclopropyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate, and methyl 2-cyclopropyl-5-hydroxy-1-benzofuran-3-carboxylate. Cyclization of methyl 3-cyclopropyl-3-oxopropanoate with ethyl chloro(arylhydrazono)ethanoates and other halohydrazones led to the formation of 3-substituted 1-aryl-5-cyclopropyl-1H-pyrazole-4-carboxylic acids, and 5-cyclopropyl-1-(quinolin-5-yl)-1H-1,2,3-triazole-4-carboxylic acid was obtained by reaction of the title compound with 5-azidoquinolines.Due to unusual structure and steric strain cyclopropane derivatives are unique compounds in the series of carbocycles [1]. Cyclopropane derivatives are widely used as building blocks in organic synthesis and for creation of combinatorial libraries. Many natural and synthetic compounds containing a cyclopropane fragment exhibit versatile biological activity [2,3]. Studies in the field of biosynthesis and metabolism of cyclopropane derivatives provide information necessary for the design of new drugs [4]. Of particular interest are heterocyclic compounds having a cyclopropyl group as substituent [5].In the present work we used methyl 3-cyclopropyl-3-oxopropanoate (I) to obtain various cyclopropylsubstituted heterocyclic compounds. It should be taken into account that some experimental conditions could

show abstract

Molecular design of pyrazolo[3,4-d]pyridazines

Cited by 36 publications

References 25 publications

Synthesis and antitumor evaluation of some new derivatives and fused heterocyclic compounds derived from thieno[2,3‐b]pyridine: Part 2

Synthesis and antitumor evaluation of some new derivatives and fused heterocyclic compounds derived from thieno[2,3‐b]pyridine: Part 2

Synthetic Routes to Pyrazole‐3(5)‐carboxylates

Methyl 3-cyclopropyl-3-oxopropanoate in the synthesis of heterocycles having a cyclopropyl substituent

Contact Info

Product

Resources

About