Synthesis and optical properties of the chloroquine enantiomers and their complexes with ferriprotoporphyrin IX in aqueous solution

Blauer, G.; Akkawi, M.; Fleischhacker, W.; Hiessböck, Romana

doi:10.1002/(sici)1520-636x(1998)10:7<556::aid-chir2>3.3.co;2-c

Cited by 5 publications

(6 citation statements)

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“…Overall stoichiometry in the complex was found to be two FPIX monomer molecules per one CQ. This confirms results from previous investigations with NMR and CD [7,24]. Both studies, however, are also in perfect agreement with our proposed 4:2 complex, since none of the previous techniques can distinguish between a 2:1 complex and multiples thereof.…”

Section: Discussionsupporting

confidence: 92%

Spin State of Chloroquine-Heme Complexes: Formation of a Hemin Tetramer Adduct

Schwedhelm¹,

Horstmann²,

Faber³

et al. 2008

TOSPECJ

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Complex formation between the antimalarial drug chloroquine and its presumed target ferriprotoporphyrin IX in three different solutions (pH 6.5, pH 9, and in a water methanol mixture) is characterized by nuclear magnetic resonance, UV spectroscopy, and mass spectrometry. NMR paramagnetic relaxation measurements are used to derive intermolecular distances between the molecules and model structures of the complexes are calculated by molecular dynamics simulations. Observation of an unusual spin state in NMR measurements leads to the postulation of a novel 4:2 stoichiometry of the complex, which is supported by mass spectrometry and UV spectroscopy.

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Section: Discussionsupporting

confidence: 92%

Spin State of Chloroquine-Heme Complexes: Formation of a Hemin Tetramer Adduct

Schwedhelm¹,

Horstmann²,

Faber³

et al. 2008

TOSPECJ

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“…Surprisingly, there are no single crystal X-ray structures reported so far. The persistent interest is not only from the fact that these compounds have attracted special attention due to its strong antibacterial, antifungal, trichomonal and keratoplastic effect [5][6][7][8][9], but also because they are important synthetic intermediates for the preparation of a variety of biologically active compounds [9].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, spectroscopy and computational studies of some biologically important hydroxyhaloquinolines and their novel derivatives

Małecki¹,

Nycz²,

Ryrych³

et al. 2010

Journal of Molecular Structure

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“…In 1998, Blauer et al 42 reported the synthesis of chloroquine enantiomers using (S)-or (R)-pyroglutamic acid as starting materials. The optically active compounds were prepared by using a 10-step sequence (Scheme 12).…”

Section: Synthesis Of (R)-chloroquine (S)-chloroquine (R)-hydroxychmentioning

confidence: 99%

Methods of Synthesis of Remdesivir, Favipiravir, Hydroxychloroquine, and Chloroquine: Four Small Molecules Repurposed for Clinical Trials during the Covid-19 Pandemic

Bujuq

2020

Synthesis

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The novel coronavirus (COVID-19) disease has rapidly evolved into a sweeping pandemic despite public health measures. Screening and development of new vaccines and antivirals are expensive and time consuming. However, the repositioning of available drugs is an essential and universal strategy in the development of new drugs and therefore should receive priority attention as well as international government and agency support. Significant drugs such as chloroquine, hydroxychloroquine, favipiravir and remdesivir, are currently undergoing clinical studies to test their efficacy and safety. Some promising results have been achieved thus far in the treatment of COVID-19. In this article we summarize and discuss the most common synthetic strategies to apply in the preparation of these drug molecules. It is hoped that this compendium will provide an accessible useful guide and reference source for scientists, researchers and academia in their battle against COVD-19.1 Introduction2 Synthesis of Chloroquine (CQ) and Hydroxychloroquine (HCQ)2.1 Synthesis of 4,7-Dichloroquinoline 1 2.2 Synthesis of 2-Amino-5-(diethylamino)pentane (Novoldiamine) 2 2.3 Synthesis of 5-(N-Ethyl-N-2-hydroxyethylamino)-2-pentylamine 4 2.4 Developed Methods for Synthesis of Chloroquine and Hydroxychloroquine2.5 Synthesis of (R)-Chloroquine, (S)-Chloroquine, (R)-Hydroxychloroquine and (S)-Hydroxychloroquine3 Synthesis of Favipiravir (Avigan)4 Synthesis of Remdesivir5 Conclusion

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Synthesis and optical properties of the chloroquine enantiomers and their complexes with ferriprotoporphyrin IX in aqueous solution

Cited by 5 publications

References 0 publications

Spin State of Chloroquine-Heme Complexes: Formation of a Hemin Tetramer Adduct

Spin State of Chloroquine-Heme Complexes: Formation of a Hemin Tetramer Adduct

Synthesis, spectroscopy and computational studies of some biologically important hydroxyhaloquinolines and their novel derivatives

Methods of Synthesis of Remdesivir, Favipiravir, Hydroxychloroquine, and Chloroquine: Four Small Molecules Repurposed for Clinical Trials during the Covid-19 Pandemic

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