Synthesis and herbicidal activities of a series of di(aminopyrazoly) ketone derivatives

Li, Junfei; Zhu, You‐Quan; Wang, Xin; Yang, Hai‐Tao

doi:10.1002/jhet.5570440401

Cited by 21 publications

(8 citation statements)

References 20 publications

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“…The synthesis of the target compounds is outlined in Schemes 1 – 3 . Compounds Ia [ 16 ], Ib [ 17 ], IIa–c [ 18 – 20 ], IIIa [ 21 ], and Iva [ 22 ] were prepared as reported in the literature.…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Antitumor Evaluation of Novel Pyrazolo[3,4-d]pyrimidine Derivatives

Kandeel

Mohamed²,

Hamid³

et al. 2012

Sci. Pharm.

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A new series of pyrazolo[3,4-d]pyrimidines has been synthesized. The new compounds were tested for their antitumor activity on 60 different cell lines, and some of the compounds were found to have potent antitumor activity. In particular, 2-hydroxybenzaldehyde [1-(4-chlorophenyl)-3-methyl-1H-pyrazolo-[3,4-d]pyrimidin-4-yl]hydrazone (VIIa) was found to be the most effective among the other derivatives, showing IC50 values of 0.326 to 4.31 μM on 57 different cell lines.

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Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Antitumor Evaluation of Novel Pyrazolo[3,4-d]pyrimidine Derivatives

Kandeel

Mohamed²,

Hamid³

et al. 2012

Sci. Pharm.

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“…The synthetic strategies employed for the synthesis of the target compounds in the current study are illustrated in (Figure 2). Compounds 1-4 were synthesized in accordance with the methods described in the literature [12,13]. Compounds 5-7 were obtained through condensation of the hydrazine compound (4) with the appropriate aromatic aldehyde.…”

Section: Chemistry Of the Compounds Under Investigation In The Current Studymentioning

confidence: 99%

Design, Synthesis, and Anticancer Screening for Repurposed Pyrazolo[3,4-d]pyrimidine Derivatives on Four Mammalian Cancer Cell Lines

et al. 2021

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The present study reports the synthesis of new purine bioisosteres comprising a pyrazolo[3,4-d]pyrimidine scaffold linked to mono-, di-, and trimethoxy benzylidene moieties through hydrazine linkages. First, in silico docking experiments of the synthesized compounds against Bax, Bcl-2, Caspase-3, Ki67, p21, and p53 were performed in a trial to rationalize the observed cytotoxic activity for the tested compounds. The anticancer activity of these compounds was evaluated in vitro against Caco-2, A549, HT1080, and Hela cell lines. Results revealed that two (5 and 7) of the three synthesized compounds (5, 6, and 7) showed high cytotoxic activity against all tested cell lines with IC50 values in the micro molar concentration. Our in vitro results show that there is no significant apoptotic effect for the treatment with the experimental compounds on the viability of cells against A549 cells. Ki67 expression was found to decrease significantly following the treatment of cells with the most promising candidate: drug 7. The overall results indicate that these pyrazolopyrimidine derivatives possess anticancer activity at varying doses. The suggested mechanism of action involves the inhibition of the proliferation of cancer cells.

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“…Its derivatives have attracted great attention due to their usefulness in the field of drug discovery, agricultural research, and energetic materials. 6−8 They are of considerable pharmacological relevance because of their antibacterial, 9 fungicidal, 10 antimicrobial, 11 herbicidal, 12 insecticidal, 13 anti-inflammatory, 14 and anticancer activities. 15 Some NH-pyrazole-containing compounds and their deriva-tives have been proved with diverse medical and biological effects.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The potassium salt, without nitrogen content in the cation, shows the lowest detonation performance. The diaminoguanidium salt (12) with the highest nitrogen content has the highest detonation velocity (8323 m s −1 ) of these salts. These new compounds have relatively low sensitivities to impact and friction, with impact sensitivities >25 J and friction sensitivities >360 N. Compound 5, with good detonation properties (Dv, 8345 m s −1 ; P, 29.7 GPa), high thermostability (T dec , 300 °C), and low sensitivities (IS, 30 J; FS, >360 N), is a promising energetic material.…”

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confidence: 99%

Energetic Tricyclic Polynitropyrazole and Its Salts: Proton-Locking Effect of Guanidium Cations

et al. 2021

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An axisymmetric polynitro-pyrazole molecule, 3,5-di(3,5-dinitropyrazol-4-yl)]-4-nitro-1H-pyrazole (5), and its salts (6–12) were prepared and fully characterized. These compounds not only show promising energetic properties but also show a unique tautomeric switch via combining different cations with the axisymmetric compound (5). Its salts (6–9) remain axisymmetric when the cations are potassium, ammonium, or amino-1,2,4-triazolium. However, when the cations are guanidiums, the salts (10–12) dramatically become asymmetric owing to the fixed proton. The introduction of guanidium cations breaks the tautomeric equilibrium by blocking the prototropic transformations and results in the switch-off effect to tautomerism. The structural constraints of 1H NMR and 13C NMR spectra provide strong evidence for the unusual structural constraint phenomenon. These stabilized asymmetric tautomers are very important from the point of molecular recognition, and this research may promote further developments in synthetic and isolation methodologies for novel bioactive pyrazole-based compounds.

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Synthesis and herbicidal activities of a series of di(aminopyrazoly) ketone derivatives

Cited by 21 publications

References 20 publications

Design, Synthesis, and Antitumor Evaluation of Novel Pyrazolo[3,4-d]pyrimidine Derivatives

Design, Synthesis, and Antitumor Evaluation of Novel Pyrazolo[3,4-d]pyrimidine Derivatives

Design, Synthesis, and Anticancer Screening for Repurposed Pyrazolo[3,4-d]pyrimidine Derivatives on Four Mammalian Cancer Cell Lines

Energetic Tricyclic Polynitropyrazole and Its Salts: Proton-Locking Effect of Guanidium Cations

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