Synthesis, In Vitro Antimicrobial and Cytotoxic Activities of Some New Pyrazolo[1,5-a]pyrimidine Derivatives

Fouda, Ahmed M.; Abbas, Hebat‐Allah S.; Ahmed, Eman H.; Shati, Ali A.; Alfaifi, Mohammad Y.; Elbehairi, Serag Eldin I.

doi:10.3390/molecules24061080

Cited by 45 publications

(35 citation statements)

References 23 publications

(24 reference statements)

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“…Because of the chemical diversity of natural products, the interest and demand to identify the actual effective compound have grown globally [ 27 ]. Plant extracts and chemically synthesized molecules have been investigated in vitro for antibacterial as well as anticancer activity [ 28 , 29 ]. Herbal medicine treatment provides some advantages over the use of single purified chemicals [ 30 ].…”

Section: Discussionmentioning

confidence: 99%

Secondary Metabolites of Saussurea costus Leaf Extract Induce Apoptosis in Breast, Liver, and Colon Cancer Cells by Caspase-3-Dependent Intrinsic Pathway

Shati

Alkahtani

Alfaifi

et al. 2020

BioMed Research International

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Background. Apoptosis, a major form of programmed cell death, plays a vital role in regulating tissue development and maintenance of homeostasis in eukaryotes. Apoptosis can occur via a death receptor-dependent extrinsic or a mitochondrial-dependent intrinsic pathway and can be induced by various chemotherapeutic agents. In this study, the anticancer activity of Saussurea costus and its mode of intervention in human cancer cells of breast, colon, and liver were investigated. Results. In this study, the bioactives of S. costus leaves were extensively extracted in five solvents of different polarity. The cytotoxicity and anticancer effect of the extracted secondary metabolites were investigated against breast (MCF-7), liver (HepG2), and colon (HCT116) cancer cell lines using a Sulphorhodamine B (SRB) assay. Secondary metabolites extracted using hexane, methanol, ethyl acetate, and chloroform had the highest cytotoxicity and thus the greatest anticancer effect on all the cancer cell lines tested (IC50; ranging from 0.25 to 2.5 μg/ml), while butanol was comparatively less active (IC50; ranging from 23.2 to 25.5 μg/ml). Further investigation using DNA flow cytometry and fluorescent microscopy revealed that the extract arrested the cells in the G1 phase of cell cycle and induced apoptosis. Furthermore, the elevated expression level of proapoptotic proteins and decreased expression level of antiapoptotic proteins confirmed that the intrinsic (mitochondrial) pathway was involved in mediating the apoptosis of cancer cells upon treatment with S. costus extract. These results altogether suggest that S. costus could be a potential anticancer agent. Conclusion. These results suggest that the S. costus extract is the potential source of the secondary metabolites that could be used as anticancer agent to treat diverse cancers of breast, colon, and liver.

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Section: Discussionmentioning

confidence: 99%

Secondary Metabolites of Saussurea costus Leaf Extract Induce Apoptosis in Breast, Liver, and Colon Cancer Cells by Caspase-3-Dependent Intrinsic Pathway

Shati

Alkahtani

Alfaifi

et al. 2020

BioMed Research International

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“…By employing arylidenemalononitriles 41a–c , it is possible to introduce an amine and a nitrile group in products 42a–c , desirable groups for subsequent reactions such as carboxamides synthesis ( Scheme 13 ). Similarly, Fouda and co-workers employ 2-(aryldiazenyl)malononitriles to obtain amines substituents at positions 7 and 5 [ 52 ].…”

Section: Synthesis and Functionalizationmentioning

confidence: 99%

Functional Pyrazolo[1,5-a]pyrimidines: Current Approaches in Synthetic Transformations and Uses As an Antitumor Scaffold

2021

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Pyrazolo[1,5-a]pyrimidine (PP) derivatives are an enormous family of N-heterocyclic compounds that possess a high impact in medicinal chemistry and have attracted a great deal of attention in material science recently due to their significant photophysical properties. Consequently, various researchers have developed different synthesis pathways for the preparation and post-functionalization of this functional scaffold. These transformations improve the structural diversity and allow a synergic effect between new synthetic routes and the possible applications of these compounds. This contribution focuses on an overview of the current advances (2015–2021) in the synthesis and functionalization of diverse pyrazolo[1,5-a]pyrimidines. Moreover, the discussion highlights their anticancer potential and enzymatic inhibitory activity, which hopefully could lead to new rational and efficient designs of drugs bearing the pyrazolo[1,5-a]pyrimidine core.

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“…[29] reported the antimicrobial activity of indole diketopiperazine alkaloids. Pyrazolo[1,5-a]pyrimidine derivatives are widely known to be used as antibacterial, antifungal and antiviral agents in biological systems [30,31].…”

Section: Biological Activitiesmentioning

confidence: 99%

Efficient synthesis of diversely substituted pyrazolo[1,5-a]pyrimidine derivatives promoted by ultrasound irradiation in water and their antibacterial activities

et al. 2020

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A green synthetic route leading to the discovery of a series of diversely substituted pyrazolo[1,5-a]pyrimidines, having CO2Et group embedded at position-2 has been unraveled in this article. A series of formylated active proton compounds that were chosen to react with a carboxylate substituted-3-aminopyrazole under ultrasonic irradiation in the presence of a mild acid as a catalyst and aqueous ethanol medium afforded the desired products. The molecular structures of all these synthesized compounds were established by their spectral and analytical data. A model molecule 3d, subjected to single-crystal X-ray crystallography analysis further confirms their molecular structure. The crystal crystallized to a monoclinic cell with P21/c space group, a = 7.468 (5) Å, b = 27.908 (17) Å, c = 7.232 (4) Å, β = 104.291 (7)o, V =1460.7(15) Å3, Z = 4, μ(MoKα) = 0.096 mm-1, Dcalc = 1.352 Mg/m3 16667 measured reflection (5.63 ≤ 2Θ ≤ 57.57°), 3720 unique (Rint = 0.0965, Rsigma = 0.0945) which were used in all calculations. The final R1 was 0.0750 (I > 2σ(I)) and wR2 was 0.2226 (all data). These compounds were further explored for their antibacterial potential, and a few of them have exhibited encouraging results.

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Synthesis, In Vitro Antimicrobial and Cytotoxic Activities of Some New Pyrazolo[1,5-a]pyrimidine Derivatives

Cited by 45 publications

References 23 publications

Secondary Metabolites of Saussurea costus Leaf Extract Induce Apoptosis in Breast, Liver, and Colon Cancer Cells by Caspase-3-Dependent Intrinsic Pathway

Secondary Metabolites of Saussurea costus Leaf Extract Induce Apoptosis in Breast, Liver, and Colon Cancer Cells by Caspase-3-Dependent Intrinsic Pathway

Functional Pyrazolo[1,5-a]pyrimidines: Current Approaches in Synthetic Transformations and Uses As an Antitumor Scaffold

Efficient synthesis of diversely substituted pyrazolo[1,5-a]pyrimidine derivatives promoted by ultrasound irradiation in water and their antibacterial activities

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