Synthesis and antiproliferative activity of 8-hydroxyquinoline derivatives containing a 1,2,3-triazole moiety

Freitas, Luiza Baptista de Oliveira; Borgati, Thiago F.; Freitas, Rossimiriam Pereira de; Ruiz, Ana Lúcia Tasca Góis; Marchetti, Gabriela M.; Carvalho, João Ernesto de; Cunha, Elaine F. F. da; Ramalho, Teodorico C.; Alves, Rosemeire Brondi

doi:10.1016/j.ejmech.2014.07.061

Cited by 59 publications

(23 citation statements)

References 48 publications

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“…This SAR information draws attention to the importance of chloro substituents for the antiproliferation activity. Several novel 8-hydroxyquinoline analogues were synthesised by Freitas et al, and the antiproliferation activity of the compounds were evaluated using several cancer cell lines ( Figure 21) [50]. Aromatic rings which had halogen substituents such as fluorine, chlorine, bromine and iodine were chosen to study the electronic and steric impacts of the substituents.…”

Section: Chloro (Cl) Groupmentioning

confidence: 99%

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A Review of the Structure–Activity Relationship of Natural and Synthetic Antimetastatic Compounds

et al. 2020

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There are innumerable anticancer compounds derived from either natural or synthetic origins. Many of these compounds have been further developed through structural modifications to not only inhibit cancer cell growth but also to exert an antimetastatic effect. This is achieved by attaching different substituents to generate different structure–activity relationships. This review highlights the effectiveness of different functional groups known to have antimigration and antiproliferation activities, such as fluoro, methoxy, methyl, amino, hydroxy, nitro, bromo, chloro, methylamino, ethoxy, carbonyl, iodo, and trifluoromethyl groups. Additionally, the positioning of these functional groups plays an important role in their anticancer activities, which was evident in one of our studies comparing analogues of a natural compound. Thus, this review suggests future recommendations for the design and development of improved anticancer drugs with higher efficacy.

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Section: Chloro (Cl) Groupmentioning

confidence: 99%

“…Freitas et al carried out a study and presented the effects of 8-hydroxyquinoline analogues on antiproliferation activity [50]. The brominated analogue 52d showed weak cytotoxic effects with the log of molar concentration that inhibits 50% net cell growth (GI 50 ) mean graph midpoint (MG MID) value = 1.3 (Table 19).…”

Section: Bromo (Br) Groupmentioning

confidence: 99%

A Review of the Structure–Activity Relationship of Natural and Synthetic Antimetastatic Compounds

et al. 2020

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“…Therefore, new anti-tumor drugs with lower side effects and better efficacy have become an urgent requirement at present. 3 Malignant cells are characterized by uncontrolled growth and proliferation. For rapid growth and proliferation, proliferating cells must take up enough of the right nutrients and energy to duplicate all macromolecular components and assemble the components into daughter cells.…”

Section: 2mentioning

confidence: 99%

Synthesis and evaluation of new sterol derivatives as potential antitumor agents

Chen

Gan

et al. 2018

RSC Adv.

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“…Biological systems are huge, they change in time and they are very sensitive to in vivo conditions like temperature and environment (Ramalho et al, 2009;Freitas et al, 2014;Nair and Miners, 2014;Jurinovich et al, 2015). These facts are remembered every day by drug designers, structural biologists, biophysicists and many other professionals that need to study these systems (Nair and Miners, 2014).…”

Section: Introductionmentioning

confidence: 99%

Could Quantum Mechanical Properties Be Reflected on Classical Molecular Dynamics? The Case of Halogenated Organic Compounds of Biological Interest

2019

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Essential to understanding life, the biomolecular phenomena have been an important subject in science, therefore a necessary path to be covered to make progress in human knowledge. To fully comprehend these processes, the non-covalent interactions are the key. In this review, we discuss how specific protein-ligand interactions can be efficiently described by low computational cost methods, such as Molecular Mechanics (MM). We have taken as example the case of the halogen bonds (XB). Albeit generally weaker than the hydrogen bonds (HB), the XBs play a key role to drug design, enhancing the affinity and selectivity toward the biological target. Along with the attraction between two electronegative atoms in XBs explained by the σ-hole model, important orbital interactions, as well as relief of Pauli repulsion take place. Nonetheless, such electronic effects can be only well-described by accurate quantum chemical methods that have strong limitations dealing with supramolecular systems due to their high computational cost. To go beyond the poor description of XBs by MM methods, reparametrizing the force-fields equations can be a way to keep the balance between accuracy and computational cost. Thus, we have shown the steps to be considered when parametrizing force-fields to achieve reliable results of complex non-covalent interactions at MM level for In Silico drug design methods.

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Synthesis and antiproliferative activity of 8-hydroxyquinoline derivatives containing a 1,2,3-triazole moiety

Cited by 59 publications

References 48 publications

A Review of the Structure–Activity Relationship of Natural and Synthetic Antimetastatic Compounds

A Review of the Structure–Activity Relationship of Natural and Synthetic Antimetastatic Compounds

Synthesis and evaluation of new sterol derivatives as potential antitumor agents

Could Quantum Mechanical Properties Be Reflected on Classical Molecular Dynamics? The Case of Halogenated Organic Compounds of Biological Interest

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