The Antimalarial Ferroquine: Role of the Metal and Intramolecular Hydrogen Bond in Activity and Resistance

2011 ◽  
Vol 6 (3) ◽  
pp. 275-287 ◽  
Author(s):  
Faustine Dubar ◽  
Timothy J. Egan ◽  
Bruno Pradines ◽  
David Kuter ◽  
Kanyile K. Ncokazi ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Intramolecular Hydrogen Bond ◽  
Intramolecular Hydrogen

Role of the bifurcated intramolecular hydrogen bond on the physico-chemical profile of the novel azo pyridone dyes

2019 ◽  
Vol 162 ◽  
pp. 562-572 ◽  
Author(s):  
Jelena Lađarević ◽  
Bojan Božić ◽  
Luka Matović ◽  
Biljana Božić Nedeljković ◽  
Dušan Mijin
Keyword(s):  
Hydrogen Bond ◽  
Intramolecular Hydrogen Bond ◽  
The Novel ◽  
Chemical Profile ◽  
Physico Chemical ◽  
Intramolecular Hydrogen

Correlating experimental electrochemistry and theoretical calculations in 2′-hydroxy chalcones: the role of the intramolecular hydrogen bond

RSC Advances ◽  
2015 ◽  
Vol 5 (63) ◽  
pp. 50929-50937 ◽  
Author(s):  
Maximiliano Martínez-Cifuentes ◽  
Ricardo Salazar ◽  
Carlos A. Escobar ◽  
Boris E. Weiss-López ◽  
Leonardo S. Santos ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Hydrogen Bond ◽  
Intramolecular Hydrogen Bond ◽  
Theoretical Calculations ◽  
Electrochemical Behaviour ◽  
Redox Properties ◽  
Methoxy Substituent ◽  
Intramolecular Hydrogen

The molecular structure and electrochemical behaviour of a series of 2′-hydroxychalcones were studied. Results show the importance of the intramolecular hydrogen bond and the methoxy substituent pattern on the redox properties of these compounds.

scholarly journals En route to phosphonato iridium(i) complexes: the decisive effect of an intramolecular hydrogen bond

2016 ◽  
Vol 45 (3) ◽  
pp. 951-962
Author(s):  
Vincenzo Passarelli ◽  
Jesús J. Pérez-Torrente ◽  
Luis A. Oro
Keyword(s):  
Hydrogen Bond ◽  
Intramolecular Hydrogen Bond ◽  
Decisive Role ◽  
Decisive Effect ◽  
Intramolecular Hydrogen

The decisive role of an intramolecular NH⋯OP hydrogen bond in the formation of a dimethyl phosphonato iridium(i) complex is shown.

Effect of the intramolecular hydrogen bond in the active metabolite analogs of leflunomide for blocking the Plasmodium falciparum dihydroorotate dehydrogenase enzyme: QTAIM, NBO, and docking study

2020 ◽  
Vol 16 ◽  
Author(s):  
Reihaneh Heidarian ◽  
Mansoureh Zahedi-Tabrizi
Keyword(s):  
Hydrogen Bond ◽  
Plasmodium Falciparum ◽  
Molecular Orbital ◽  
Intramolecular Hydrogen Bond ◽  
Active Metabolite ◽  
Chemical Hardness ◽  
Dihydroorotate Dehydrogenase ◽  
Molecular Orbital Analysis ◽  
Intramolecular Hydrogen ◽  
Orbital Analysis

: Leflunomide (LFM) and its active metabolite, teriflunomide (TFM), have drawn a lot of attention for their anticancer activities, treatment of rheumatoid arthritis and malaria due to their capability to inhibit dihydroorotate dehydrogenase (DHODH) and Plasmodium falciparum dihydroorotate dehydrogenase (PfDHODH) enzyme. In this investigation, the strength of intramolecular hydrogen bond (IHB) in five analogs of TFM (ATFM) has been analyzed employing density functional theory (DFT) using B3LYP/6-311++G (d, p) level and molecular orbital analysis in the gas phase and water solution. A detailed electronic structure study has been performed using the quantum theory of atoms in molecules (QTAIM) and the hydrogen bond energies (EHB) of stable conformer obtained in the range of 76-97 kJ/mol, as a medium hydrogen bond. The effect of substitution on the IHB nature has been studied by natural bond orbital analysis (NBO). 1H NMR calculations show an upward trend in the proton chemical shift of the enolic proton in the chelated ring (14.5 to 15.7ppm) by increasing the IHB strength. All the calculations confirmed the strongest IHB in 5-F-ATFM and the weakest IHB in 2-F-ATFM. Molecular orbital analysis, including the HOMO-LUMO gap and chemical hardness, was performed to compare the reactivity of inhibitors. Finally, molecular docking analysis was carried out to identify the potency of inhibition of these compounds against PfDHODH enzyme.

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