Aminopyrimidines: Recent synthetic procedures and anticancer activities

Filho, Eclair Venturini; Pinheiro, Erick M.C.; Pinheiro, Sérgio; Greco, Sandro J.

doi:10.1016/j.tet.2021.132256

Cited by 24 publications

(12 citation statements)

References 207 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To further demonstrate the regioselectivity of this mechanochemical Minisci reaction, diverse 2-substituted pyrimidines containing (hetero)arenes, aromatic amines, and alkylamines 1g – 1r were tested, and the results showed that only C4 alkylation of pyrimidines occurred in all cases. Of note, the mechanochemical conditions allowed the introduction of the sensitive amino group ( 3ra ), which provides synthetic handles for further derivatization and application in drug synthesis . Moreover, the reaction was not restricted to substituted pyrimidines, as pyridines were also suitable substrates.…”

supporting

confidence: 72%

Mechanochemical Magnesium-Mediated Minisci C–H Alkylation of Pyrimidines with Alkyl Bromides and Chlorides

Ying

Yang

et al. 2021

Org. Lett.

View full text Add to dashboard Cite

A novel method to synthesize 4-alkylpyrimidines by the mechanochemical magnesium-mediated Minisci reaction of pyrimidine derivatives and alkyl halides has been reported. The reaction process operates with a broad substrate scope and excellent regioselectivity under mild conditions with no requirement of transition-metal catalysts, solvents, and inert gas protection. The practicality of this protocol has been demonstrated by the up-scale synthesis, mechanochemical product derivatization, and antimalarial drug pyrimethamine preparation.

show abstract

supporting

confidence: 72%

Mechanochemical Magnesium-Mediated Minisci C–H Alkylation of Pyrimidines with Alkyl Bromides and Chlorides

Ying

Yang

et al. 2021

Org. Lett.

View full text Add to dashboard Cite

show abstract

“…Every year, the global prevalence of cancer rises, as does the resistance to current chemotherapeutic agents like cisplatin; nowadays, one of the main goals of the pharmaceutical industry is the development of more effective drugs for the treatment of cancer [55,56].…”

Section: Discussionmentioning

confidence: 99%

“…Within the pyrimidines, the aminopyrimidine scaffold is present in the structure of a wide variety of natural and synthetic products, such as Thiamine (vitamin B1), Meridianins (a class of marine alkaloids), or Imatinib, a drug used against leukemia, which displays biological activities such as neuroprotection, antibiotic, antidiabetic, anti-Alzheimer, and anticancer. Among the large family of aminopyrimidines, the 2-aminopyrimidine isomer is the most studied, mainly because of its versatility as a starting material for synthesizing many other bioactive compounds [55].…”

Section: Discussionmentioning

confidence: 99%

2-Aminopyrimidinium Decavanadate: Experimental and Theoretical Characterization, Molecular Docking, and Potential Antineoplastic Activity

et al. 2021

View full text Add to dashboard Cite

The interest in decavanadate anions has increased in recent decades, since these clusters show interesting applications as varied as sensors, batteries, catalysts, or new drugs in medicine. Due to the capacity of the interaction of decavanadate with a variety of biological molecules because of its high negative charge and oxygen-rich surface, this cluster is being widely studied both in vitro and in vivo as a treatment for several global health problems such as diabetes mellitus, cancer, and Alzheimer’s disease. Here, we report a new decavanadate compound with organic molecules synthesized in an aqueous solution and structurally characterized by elemental analysis, infrared spectroscopy, thermogravimetric analysis, and single-crystal X-ray diffraction. The decavanadate anion was combined with 2-aminopyrimidine to form the compound [2-ampymH]6[V10O28]·5H2O (1). In the crystal lattice, organic molecules are stacked by π–π interactions, with a centroid-to-centroid distance similar to that shown in DNA or RNA molecules. Furthermore, computational DFT calculations of Compound 1 corroborate the hydrogen bond interaction between pyrimidine molecules and decavanadate anions, as well as the π–π stacking interactions between the central pyrimidine molecules. Finally, docking studies with test RNA molecules indicate that they could serve as other potential targets for the anticancer activity of decavanadate anion.

show abstract

“…2) such as Imatinib (Glivec®) 6 , Pazopanib (Votrient®) 7 , Encorafenib (Braftovi®) 8 , as well as many drug candidates undergoing clinical phase trials. 16…”

Section: Introductionmentioning

confidence: 99%

Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells

et al. 2023

View full text Add to dashboard Cite

show abstract

Aminopyrimidines: Recent synthetic procedures and anticancer activities

Cited by 24 publications

References 207 publications

Mechanochemical Magnesium-Mediated Minisci C–H Alkylation of Pyrimidines with Alkyl Bromides and Chlorides

Mechanochemical Magnesium-Mediated Minisci C–H Alkylation of Pyrimidines with Alkyl Bromides and Chlorides

2-Aminopyrimidinium Decavanadate: Experimental and Theoretical Characterization, Molecular Docking, and Potential Antineoplastic Activity

Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells

Contact Info

Product

Resources

About