Synthesis of pyrazole-4-carbohydrazide derivatives of pharmaceutical interest

Daidone, Giuseppe; Raffa, Demetrio; Plescia, Fulvio; Maggio, Benedetta; Roccaro, Angela

doi:10.3998/ark.5550190.0003.b20

Cited by 8 publications

(6 citation statements)

References 3 publications

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“…Sigma-Aldrich provided all of the compounds, which were utilized without additional purification. Compounds 2 27 , 4 32 and 6 39 were synthesized according to the previously reported procedures.…”

Section: Methodsmentioning

confidence: 99%

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Design, synthesis and computational study of new benzofuran hybrids as dual PI3K/VEGFR2 inhibitors targeting cancer

El-Khouly

Henen

El‐Sayed

et al. 2022

Sci Rep

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Design and synthesis of a new series of benzofuran derivatives has been performed. 1H-NMR, 13C-NMR, elemental analysis, and IR were used to confirm the structures of the produced compounds. Hepatocellular carcinoma (HePG2), mammary gland breast cancer (MCF-7), epithelioid carcinoma cervical cancer (Hela), and human prostate cancer are used to test anticancer activity (PC3). In compared to DOX (4.17–8.87 µM), Compound 8 demonstrated the highest activity against HePG and PC3 cell lines, with an IC50 range of 11–17 µM. Compound 8 inhibited PI3K and VEGFR-2 with IC50 values of 2.21 and 68 nM, respectively, compared to 6.18 nM for compound LY294002 and 31.2 nM for compound sorafenib as PI3K and VEGFR-2 reference inhibitors, selectively. The molecular docking and binding affinity of the generated compounds were estimated and studied computationally utilizing molecular operating environment software as a PI3K and VEGFR-2 inhibitor (MOE). In conclusion, compound 8 exhibited significant action against hepatocellular and cervical cancer cell lines. Mechanistic study showed that it had a dual inhibitory effect against PI3K and VEGFR-2.

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Section: Methodsmentioning

confidence: 99%

“…)ethylidene]hydrazine (6) 39 . In ethanol, 1-(Benzofuran-2-yl)ethan-1-one (2) (1.6 g, 10 mmol) was refluxed for 2 h with hydrazine hydrate 99% (0.5 g, 0.5 ml, 10 mmol) The white precipitate was filtered before being crystallized from ethanol.…”

Section: Preparation Of (E)-[1-(benzofuran-2-ylmentioning

confidence: 99%

Design, synthesis and computational study of new benzofuran hybrids as dual PI3K/VEGFR2 inhibitors targeting cancer

El-Khouly

Henen

El‐Sayed

et al. 2022

Sci Rep

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“…In 2015, Venkatesan et al [24] reported the reaction of the pyrazole was obtained by reacting 41 with triethyl orthoformate [25] (Scheme 13). Raffa et al [26] reported that condensation of 5-amino-1H-…”

Section: From Amino Pyrazole 4-carboxamide Derivativesmentioning

confidence: 99%

Pyrazolo[3,4‐d]pyrimidine scaffold: A review on synthetic approaches and EGFR and VEGFR inhibitory activities

Kassab

2022

Archiv der Pharmazie

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The pyrazolo[3,4‐d]pyrimidine core has received a lot of interest from the medicinal chemistry community as a promising framework for drug design and discovery. It is an isostere of the adenine ring of adenosine triphosphate, which allows it to mimic kinase active site hinge region binding contacts. This scaffold has a wide pharmacological and biological value, one of which is as an anticancer agent. Many successful anticancer medicines have been designed and synthesized using pyrazolo[3,4‐d]pyrimidine as a key pharmacophore. The main synthetic routes of pyrazolo[3,4‐d]pyrimidines as well as their recent developments as promising anticancer agents acting as endothelial growth factor receptors and vascular endothelial growth factor receptor inhibitors, published in the time frame from 1999 to 2022, are summarized in this review to set the direction for the design and synthesis of novel pyrazolo[3,4‐d]pyrimidine derivatives for clinical deployment in cancer treatment.

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“…There are several approaches reported in the synthesis of pyrazolo [3,4-d]pyrimidines, for instance: reaction of 5-amino-pyrazole-4-carbohydrazides with formamide and hydrazine hydrate under microwave irradiation (Todorovic et al 2011), or with urea anddecaline (Ghorab et al 2010) or with benzoyl chloride derivatives and triethylorthoformate (Daidone et al 2002). There are reports on the reaction of ethyl 5-amino-1H-pyrazole-4-carboxylates with hydrazine hydrate and triethylorthoformate (Ghorab et al 2010) and also with formamide or benzoyl isothiocyanate (Carraro et al 2006) as well as reaction of 4-hydrazinylpyrimidine derivatives with isocyanates (Bhuyan et al 2002).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and in vitro antibacterial evaluation of 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidines

et al. 2017

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Pyrazolo[3,pyrimidines are one of the most important classes of fused heterocyclic compounds which exhibit a broad range of biological and medicinal properties. They are known as anticancer, antifungal, antibacterial, antiviral and anti-inflammatory agents. In this study, some new 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidine derivatives were prepared via reaction of 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile with various nitriles in the presence of sodium ethoxide as catalyst. The inhibitory properties of synthesized compounds were studied according to CLSI guidelines against some pathogenic bacteria including four gram-positive strains (Streptococcus pyogenes, Staphylococcus aureus, Bacillus cereus and Bacillus subtilis subsp. spizizenii) and three gramnegative strains (Pseudomonas aeruginosa, Shigella flexneri and Salmonella enterica subsp. enterica). The antibacterial effects of all derivatives were compared with those of antibiotics belonging to different classes. The values were reported as inhibition zone diameter (IZD), minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC). The effect of substituents on the biological activity of derivatives was discussed as well. The inhibitory effect of compound 6a, was shown to be the most, with MIC values in the range of 32-4096 lg/mL. Since most of the synthesized compounds were effective against Streptococcus pyogenes and Pseudomonas aeruginosa, they can be considered as inhibitors of these two bacteria.

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Synthesis of pyrazole-4-carbohydrazide derivatives of pharmaceutical interest

Cited by 8 publications

References 3 publications

Design, synthesis and computational study of new benzofuran hybrids as dual PI3K/VEGFR2 inhibitors targeting cancer

Design, synthesis and computational study of new benzofuran hybrids as dual PI3K/VEGFR2 inhibitors targeting cancer

Pyrazolo[3,4‐d]pyrimidine scaffold: A review on synthetic approaches and EGFR and VEGFR inhibitory activities

Synthesis and in vitro antibacterial evaluation of 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidines

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