Design, synthesis and structure–activity relationship study of novel pyrazole-based heterocycles as potential antitumor agents

Farag, Ahmad M.; Ali, Korany A.; Eldebss, Taha M. A.; Mayhoub, Abdelrahman S.; Amr, Abd El‐Galil E.; Abdel‐Hafez, Naglaa A.; Abdulla, Mohamed M.

doi:10.1016/j.ejmech.2010.09.054

Cited by 68 publications

(18 citation statements)

References 41 publications

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“…Thus, treatment of 1-(4-fluorophenyl)-5-phenyl-3-((E)-3-phenylacryloyl)-1H-pyrazole-4-carbonitrile (4) with guanidine under reflux temperature afforded a single product identified as 3-(2-amino-6-phenylpyrimidin-4-yl)-1-(4-fluorophenyl)-5-phenyl-1H-pyrazole-4-carbonitrile (7). The IR spectrum of compound 7 showed amino and nitrile absorption bands at 3430-3320 and 2231 cm -1 , respectively.…”

Section: Resultsmentioning

confidence: 98%

“…Compounds A, B, and C ( Fig. 1) are examples of the synthesized compounds, showing significant cytotoxic activity in the nanomolar range against certain types of breast and ovarian tumor with tolerable toxicity [6,7].…”

Section: Introductionmentioning

confidence: 99%

“…Additionally, some pyrazole derivatives show potential anticancer and antibacterial activities [4,5]. Previously, we synthesized several 4-cyano-1,5-diphenylpyrazoles attached to different heterocyclic ring systems at position 3 and tested their antiestrogenic effects and cytotoxic properties against estrogendependent tumors [6,7]. Compounds A, B, and C ( Fig.…”

Section: Introductionmentioning

confidence: 99%

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Facile synthetic approaches for new series of pyrazole-4-carbonitrile derivatives

et al. 2015

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Aldol condensation of 3-acetyl-1-(4-fluorophenyl)-5-phenyl-1H-pyrazole-4-carbonitrile with benzaldehyde afforded 1-(4-fluorophenyl)-5-phenyl-3-((E)-3-phenylacryloyl)-1H-pyrazole-4-carbonitrile, which in turn reacted with a series of 1,2-and 1,3-binucleophiles to afford new substituted pyrazoles, pyrimidines, and condensed azolopyrimidine derivatives attached to pyrazole scaffold at position 3. Moreover, multicomponent condensation reactions (MCRs) were used as an alternative method, and 1 H-13 C heteronuclear single quantum coherence (HSQC) in addition to heteronuclear multiple-bond correlation (HMBC) spectra were used for full confirmation of a selected example of these compounds. The reactivity of 1-(4-fluorophenyl)-5-phenyl-3-((E)-3-phenylacryloyl)-1H-pyrazole-4-carbonitrile towards active methylene derivatives, including malononitrile and ethyl cyanoacetate, was explored and afforded 2

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Section: Resultsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Facile synthetic approaches for new series of pyrazole-4-carbonitrile derivatives

et al. 2015

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“…Compounds that contain the pyrazole moiety are known to exhibit a wide range of biological properties such as anticancer [1], anticonvulsant [2], antiviral [3], anti-tumor [4], analgesic, sedative [5], antimicrobial [6] and anti-in ammatory activities [7]. In addition, pyrazoles have a wide variety of application in the agrochemical and pharmaceutical industries [8].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of N′-(4-nitrobenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide, C₁₇H₁₃N₅O₃

Karrouchi¹,

Radi

Ansar

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

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“…The azomethine carbon C(4) was assigned to the signal at 146.41 ppm. The signal resonated at lower field due to conjugative effect from N3 = N2-C1 core of the molecule (Farag et al, 2010). In the benzonitrile ring, C7 and C10 integrated to two carbon atoms each due to equivalent chemical environment.…”

Section: Nmrmentioning

confidence: 99%

Transition Metal Complexes of (E)-N’-(4-cyanobenzylidene)nicotinohydrazide): Synthesis, Structural and Anti-Mycobacterial Activity Study

Ogunniran¹,

Adekoya²,

Eromosele³

et al. 2015

J. of Applied Sciences

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A B S T R A C T One step condensation of nicotinic acid hydrazide and 4-cyanobenzaldehyde formed a bidentate acylhydrazone ligand (HL 5 ). The acylhydrazone was characterized by ESI mass spectrometer, CHN analyzer, IR spectrometer, 1 H-NMR, 13 C-NMR and 2D NMR (COSY and HSQC). Thereafter, Mn(II), Mo(V), Fe(II), Cu(II) and Zn(II) complexes of the acylhydrazone ligand were synthesized and characterized based on conductivity measurements, melting point determination, CHN analysis, AAS, magnetic measurement, UV/Visible study, IR spectroscopy, ESR and TGA/DTA studies. The information obtained corroborated results from powder X-ray analysis to arrive at the model structures for the complexes. In vitro antimycobacterial properties of the compounds were evaluated against Mycobacterium tuberculosis H37Rv by using micro-diluted method. The result obtained revealed that HL 5 , Mn(II), Mo(V), Cu(II) and Zn(II) complexes exhibited promising antitubercular activity. Zn(II) complex had the highest MIC value of 0.62 μg MLG 1 , while Fe(II) complex exhibited the lowest MIC value of 1.15 μg MLG 1 . However, the result of cytotoxicity study indicated that acylhydrazone and Zn(II) complex with IC 50 of 2.17 and 1.72 μM, respectively were not toxic compared to isoniazid. Mn(II) complex was however found to be the most toxic.

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Design, synthesis and structure–activity relationship study of novel pyrazole-based heterocycles as potential antitumor agents

Cited by 68 publications

References 41 publications

Facile synthetic approaches for new series of pyrazole-4-carbonitrile derivatives

Facile synthetic approaches for new series of pyrazole-4-carbonitrile derivatives

Crystal structure of N′-(4-nitrobenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide, C₁₇H₁₃N₅O₃

Transition Metal Complexes of (E)-N’-(4-cyanobenzylidene)nicotinohydrazide): Synthesis, Structural and Anti-Mycobacterial Activity Study

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Design, synthesis and structure–activity relationship study of novel pyrazole-based heterocycles as potential antitumor agents

Cited by 68 publications

References 41 publications

Facile synthetic approaches for new series of pyrazole-4-carbonitrile derivatives

Facile synthetic approaches for new series of pyrazole-4-carbonitrile derivatives

Crystal structure of N′-(4-nitrobenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide, C17H13N5O3

Transition Metal Complexes of (E)-N’-(4-cyanobenzylidene)nicotinohydrazide): Synthesis, Structural and Anti-Mycobacterial Activity Study

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Crystal structure of N′-(4-nitrobenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide, C₁₇H₁₃N₅O₃