Mefloquine derivatives: Crystal structures and anti-tubercular activities of diphenyl[((R*,S*)-2,8-bis(trifluoromethyl)quinolin-4-yl)-piperidin-2-yl-methanolato-O,N]boron and (±)-erythro-mefloquinium tetraphenylborate solvates

Wardell, Jámes L.; Souza, Marcus V. N. de; Wardell, Solange M. S. V.; Lourenço, Maria Cristina S.

doi:10.1016/j.molstruc.2011.01.019

Cited by 11 publications

(2 citation statements)

References 46 publications

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“…The MIC values from in vitro assays against M. tuberculosis for mefloquinium tetraphenylborate and the mefloquine oxazaborolidine derivative MQ-69 ∙EtOH were 12 and 50 µg/mL, respectively. The former was presented to be slightly more active than mefloquine hydrochloride (25 µg/mL), yet worse than ethambutol or rifampicin (2–3 µg/mL) [ 72 ].…”

Section: Mefloquine (Mq)mentioning

confidence: 99%

A Review of Modifications of Quinoline Antimalarials: Mefloquine and (hydroxy)Chloroquine

2022

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Late-stage modification of drug molecules is a fast method to introduce diversity into the already biologically active scaffold. A notable number of analogs of mefloquine, chloroquine, and hydroxychloroquine have been synthesized, starting from the readily available active pharmaceutical ingredient (API). In the current review, all the modifications sites and reactivity types are summarized and provide insight into the chemistry of these molecules. The approaches include the introduction of simple groups and functionalities. Coupling to other drugs, polymers, or carriers afforded hybrid compounds or conjugates with either easily hydrolyzable or more chemically inert bonds. The utility of some of the compounds was tested in antiprotozoal, antibacterial, and antiproliferative assays, as well as in enantiodifferentiation experiments.

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Section: Mefloquine (Mq)mentioning

confidence: 99%

A Review of Modifications of Quinoline Antimalarials: Mefloquine and (hydroxy)Chloroquine

2022

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“…In addition, piperidines have widespread pharmacological applications as antibacterial, antifungal, anticancer, anti-tuberculosis, elastase inhibitors, antiobesity, antianalgesic, acetylcholine serine protease inhibitor, antihypertensive, antidepressant, neuroprotective, and antipsychotics. , Due to the significant relevance of piperidine derivatives belonging to the pharmacologically active scaffold in different therapeutic drugs, their synthesis has been extensively studied in the literature. , …”

Section: Introductionmentioning

confidence: 99%

Exploring Highly Functionalized Tetrahydropyridine as a Dual Inhibitor of Monoamine Oxidase A and B: Synthesis, Structural Analysis, Single Crystal XRD, Supramolecular Assembly Exploration by Hirshfeld Surface Analysis, and Computational Studies

et al. 2022

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Ethyl 4-(4-fluorophenylamino)-2,6-bis(4-(trifluoromethyl)phenyl)-1-(4-fluoro-phenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate ( FTEAA ) has been synthesized efficiently in an iodine-catalyzed five-component reaction of 4-fluoroaniline, 4-trifluoromethyl benzaldehyde, and ethyl acetoacetate in methanol at 55 °C for 12 h. Various spectro-analytical techniques such as 1 H and 13 C NMR and Fourier-transform infrared spectroscopy have validated the structure of FTEAA . Further confirmation of the structure of FTEAA has been established on the basis of single-crystal X-ray diffraction analysis. The supramolecular assembly of FTEAA in terms of strong and comparatively weak noncovalent interactions is fully investigated by Hirshfeld surface analysis, the interaction energy between pairs of molecules, and energy frameworks. The void analysis is conducted to explore the strength and stability of the crystal structure. Furthermore, molecular docking analysis was computationally performed to see the potential intermolecular interactions between the selected proteins and FTEAA . The binding interaction energies are found to be −8.8 and −9.6 kcal/mol for the proteins MAO-B (PDB ID: 2V5Z ) and MAO-A (PDB ID: 2Z5X ), respectively. These reasonably good binding energies (more negative values) indicate the efficient associations between the FTEAA and target proteins. The proteins and FTEAA were also analyzed for intermolecular interactions. FTEAA and proteins interact in a variety of ways, like conventional hydrogen bonds, carbon–hydrogen bonds, alkyl, π-alkyl, and halide interactions.

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Structures of Two Rotamers of the HCl Salt of 4-Methyl-2-[(1E)-[2-(quinolin-4-yl)hydrazin-1-ylidene]methyl]phenol: Different Supramolecular Arrays

et al. 2013

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Mefloquine derivatives: Crystal structures and anti-tubercular activities of diphenyl[((R,S)-2,8-bis(trifluoromethyl)quinolin-4-yl)-piperidin-2-yl-methanolato-O,N]boron and (±)-erythro-mefloquinium tetraphenylborate solvates

Cited by 11 publications

References 46 publications

A Review of Modifications of Quinoline Antimalarials: Mefloquine and (hydroxy)Chloroquine

A Review of Modifications of Quinoline Antimalarials: Mefloquine and (hydroxy)Chloroquine

Exploring Highly Functionalized Tetrahydropyridine as a Dual Inhibitor of Monoamine Oxidase A and B: Synthesis, Structural Analysis, Single Crystal XRD, Supramolecular Assembly Exploration by Hirshfeld Surface Analysis, and Computational Studies

Structures of Two Rotamers of the HCl Salt of 4-Methyl-2-[(1E)-[2-(quinolin-4-yl)hydrazin-1-ylidene]methyl]phenol: Different Supramolecular Arrays

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