Two 5-Methoxyindole Carboxylic Acid-Derived Hydrazones of Neuropharmacological Interest: Synthesis, Crystal Structure, and Chemiluminescent Study of Radical Scavenging Properties

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creativework.keywordshydrazone derivatives of 5-methoxyindole carboxylic acid, hypochlorite ions, iron-induced oxidative damage, radical scavenging, single-crystal X-ray diffraction, superoxide anion radical
creativework.publisherMultidisciplinary Digital Publishing Institute (MDPI)en
dc.contributor.authorAnastassova N.
dc.contributor.authorHristova-Avakumova N.
dc.contributor.authorRusew R.
dc.contributor.authorShivachev B.
dc.contributor.authorYancheva D.
dc.date.accessioned2024-07-10T14:27:06Z
dc.date.accessioned2024-07-10T14:51:33Z
dc.date.available2024-07-10T14:27:06Z
dc.date.available2024-07-10T14:51:33Z
dc.date.issued2024-05-01
dc.description.abstractGiven the importance of molecular structure in pharmacological activity and interaction with biological receptors, we conducted a study on the 3,4-dihydroxybenzaldehyde hydrazone derivative of 5-methoxy-indole carboxylic acid (5MICA) and a newly synthesised analogue bearing a 2-methoxy-4-hydroxyphenyl ring using single-crystal X-ray diffraction. We studied the ability of the two compounds to scavenge hypochlorite ions using luminol-enhanced chemiluminescence and their potential to modulate oxidative damage induced by iron on the biologically significant molecules lecithin and deoxyribose in order to evaluate possible antioxidant and prooxidant effects. The X-ray study revealed highly conserved geometry and limited rotation and deformation freedom of the respective indole and phenyl fragments. Interestingly, a conformational difference between the two independent molecules in the asymmetric unit of 3b was found. The X-ray study revealed a combination of hydrogen bonding interactions, short contacts, and π–π stacking stabilizing the specific three-dimensional packing of the molecules of 3a and 3b in the crystal structures. The three-dimensional packing of the molecules of 3b produced a zigzag layering projected along the c-axis. Both compounds effectively decreased luminol-dependent chemiluminescence in model systems with KO2-produced superoxide. They displayed opposite effects when applied in a xanthine/xanthine oxidase system. The hydrazones of 5MICA do not trigger a prooxidant effect or subsequent toxicity under conditions of iron-induced oxidative stress. The 3,4-dihydroxy-substituted derivative demonstrated excellent radical scavenging properties in all model systems, making it the lead compound for the development of compounds with combined neuroprotective and antioxidant properties.
dc.identifier.doi10.3390/cryst14050396
dc.identifier.issn2073-4352
dc.identifier.scopusSCOPUS_ID:85194264818en
dc.identifier.urihttps://rlib.uctm.edu/handle/123456789/956
dc.language.isoen
dc.source.urihttps://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85194264818&origin=inward
dc.titleTwo 5-Methoxyindole Carboxylic Acid-Derived Hydrazones of Neuropharmacological Interest: Synthesis, Crystal Structure, and Chemiluminescent Study of Radical Scavenging Properties
dc.typeArticle
oaire.citation.issue5
oaire.citation.volume14
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