Intramolecular Hydrogen Bonds in Conformers of Quinine and Quinidine: An HF, MP2 and DFT Study

Bilonda, Mireille K.; Mammino, Liliana

doi:10.3390/molecules22020245

Cited by 13 publications

(5 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…77 Isolated quinoline alkaloids have been investigated as possible antimalarial agents since quinine was found to inhibit the endocytosis of P. falciparum 78 and quinidine, an erythro diastereoisomer of quinine, was also found to exhibit significant antimalarial activity. 79…”

Section: Biological Activities Of Quinoline and Quinazoline Alkaloidsmentioning

confidence: 99%

Biologically active quinoline and quinazoline alkaloids part II

Shang

Morris‐Natschke

Yang

et al. 2018

Medicinal Research Reviews

160

View full text Add to dashboard Cite

To follow-up on our prior Part I review, this Part II review summarizes and provides updated literature on novel quinoline and quinazoline alkaloids isolated during the period of 2009-2016, together with the biological activity and the mechanisms of action of these classes of natural products. Over 200 molecules with a broad range of biological activities, including antitumor, antiparasitic and insecticidal, antibacterial and antifungal, cardioprotective, antiviral, anti-inflammatory, hepatoprotective, antioxidant, anti-asthma, antitussive, and other activities, are discussed. This survey should provide new clues or possibilities for the discovery of new and better drugs from the original naturally occurring quinoline and quinazoline alkaloids.

show abstract

Section: Biological Activities Of Quinoline and Quinazoline Alkaloidsmentioning

confidence: 99%

Biologically active quinoline and quinazoline alkaloids part II

Shang

Morris‐Natschke

Yang

et al. 2018

Medicinal Research Reviews

160

View full text Add to dashboard Cite

show abstract

“…In Fig. 3 we can observe the HOMO (left) and LUMO (right) pro les for chloroquine (above) and quinine (below), which demonstrate distinct nucleophilic and electrophilic characteristics [37]. The HOMO contributions for both molecules are mainly located on the heterocycle rings, exhibiting symmetry in all groups for chloroquine, particularly on nitrogen atoms, with no contribution from the chloro moiety.…”

Section: Electron Donation Capacity Of Chloroquine Related To Quininementioning

confidence: 93%

Structural requirements for nucleophilicity and antioxidant capacity on quinoline derivatives: a theoretical study

Borges

Santos

et al. 2023

Preprint

View full text Add to dashboard Cite

Context Quinoline derivatives play a crucial role in antimalarial therapy, and their biological properties are highly dependent on the basicity, particularly on the amine groups. The Amine moieties significantly contribute to the antioxidant capacity of quinoline derivatives through electron transfer mechanisms. Notably, each amine group has a distinct contribution to the antioxidant capacity, with the aliphatic amine displaying a potent electron donating capacity, the exo-aromatic amine showing an intermediate capacity, and the endo-aromatic amine demonstrating the least potent capacity. Our findings reveal a synergistic effect between the 4-amino-quinoline and tertiary amine in quinoline derivatives, enhancing their overall antioxidant capacity. However, the presence of the chlorine atom decreases its contribution as an electron withdrawing group. In comparison, chloroquine exhibits a higher antioxidant capacity than quinine, and their respective electron donation abilities are correlated with their pKa values. The synergistic effect between the 4-amino-quinoline and tertiary amine is particularly evident in chloroquine, surpassing the antioxidant capacity of 6-methoxy-4-methyl-quinoline moiety in quinine. Additionally, we have successfully proposed two new strategies for the development of chloroquine derivatives. Methods A theoretical study was conducted to investigate the structure-nucleophilicity and antioxidant capacity of quinoline derivatives, specifically chloroquine and quinine, through electron transfer using DFT/B3LYP/6–31 + G(d,p) methods. The HOMO values were utilized to assess nucleophilicity, while the ionization potential was indicative of electron donating capacity. To explore different aspects of the molecules, four approaches of molecular modifications were proposed: molecular fragmentation, molecular modification on amine moieties, and molecular association. These approaches aimed to provide insights into the relationships between molecular structure and nucleophilicity or antioxidant capacity. The study also involved the development of new strategies in drug design, leveraging theoretical methods to explore potential modifications and optimizations for quinoline derivatives.

show abstract

“…33,35 This means that the cation based on cinchona alkaloid inuenced the physical state and the viscosity of the obtained products. These phenomena may be partly attributed to the presence of the hydroxyl moiety in the alkaloid-based cation, which is a donor of particularly strong hydrogen bonds 46 that are only partially disrupted by the introduction of an organic anion. 33 The analysis of 1 H NMR, 13 C NMR and FT-IR spectra conrmed that the chemical structures of the obtained ILs were correct.…”

Section: Synthesis and Identicationmentioning

confidence: 99%