Novel aminoalkylated chalcone: Synthesis, biological evaluation, and docking simulation as potent antimalarial agents

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dc.contributor.authorSyahri, Jufrizalen_US
dc.contributor.authorNasution, Hasmalinaen_US
dc.contributor.authorNurohmah, Beta Achromien_US
dc.contributor.authorPurwono, Bambangen_US
dc.contributor.authorYuanita, Emmyen_US
dc.date.accessioned2020-10-16T08:56:57Z
dc.date.available2020-10-16T08:56:57Z
dc.date.issued2020-06
dc.description.abstractThree chalcone derivatives with amine groups (4a–c) were synthesized and evaluated for their antimalarial activity.Three aminoalkylated chalcone derivatives (4a–c) have been prepared through Claisen–Schmidt condensation reactionfrom vanillin and chloroacetophenone, followed by the Mannich reaction to add amine group. The structure of thecompounds was confirmed by the spectrophotometric analysis using mass spectrometers (MS) and proton and carbonnuclear magnetic resonance (1H- and 13C-NMR) spectroscopy. Antimalarial activity of 4a–c was evaluated againstPlasmodium falciparum (3D7) strain, and the molecular docking of 4b was performed to understand the interactionagainst Pf DHFR-TS protein (1J3I.pdb). The prepared aminoalkylated chalcone (4a–c) was obtained in a yield of 80%,75%, and 70%. The addition of morpholine (4a), piperidine (4b), and diethylamine (4c) as amine groups significantlycould improve the antimalarial activity with IC50 of 0.62, 0.54, and 1.12 µM, respectively (strong activity), comparedwith the chalcone without amine group (3) with IC50 of 25.84 µM (moderate activity). The molecular docking ofcompound 4b exhibited strong hydrogen bond interaction with ILE112, ILE64, SER111, SER108, ASP54, TYR170,and PRO113 residues with CDOCKER interaction energy of −48.84 kcal/mol. Thus, aminoalkylated chalcone couldbe proposed for further studies and developed into antimalarial drug candidatesen_US
dc.identifier.affiliationsDepartment of Chemistry, Universitas Muhammadiyah Riau, Pekanbaru, Indonesia.en_US
dc.identifier.affiliationsDepartment of Chemistry, Universitas Muhammadiyah Riau, Pekanbaru, Indonesia.en_US
dc.identifier.affiliationsDepartment of Chemistry, Universitas Gadjah Mada, Yogyakarta, Indonesiaen_US
dc.identifier.affiliationsDepartment of Chemistry, Universitas Gadjah Mada, Yogyakarta, Indonesiaen_US
dc.identifier.affiliationsDepartment of Chemistry, Universitas Mataram, Mataram, Indonesia.en_US
dc.identifier.citationSyahri Jufrizal, Nasution Hasmalina, Nurohmah Beta Achromi, Purwono Bambang, Yuanita Emmy. Novel aminoalkylated chalcone: Synthesis, biological evaluation, and docking simulation as potent antimalarial agents. Journal of Applied Pharmaceutical Science. 2020 Jun; 2020 Jun: 001-005en_US
dc.identifier.issn2231-3354
dc.identifier.placeIndiaen_US
dc.identifier.urihttps://imsear.searo.who.int/handle/123456789/210762
dc.languageenen_US
dc.publisherOpen Science Publishers LLPen_US
dc.relation.issuenumber6en_US
dc.relation.volume10en_US
dc.source.urihttps://dx.doi.org//10.7324/JAPS.2020.10601en_US
dc.subjectAntimalarialen_US
dc.subjectchalconeen_US
dc.subjectdockingen_US
dc.subjectmannich reactionen_US
dc.subject3D7.en_US
dc.titleNovel aminoalkylated chalcone: Synthesis, biological evaluation, and docking simulation as potent antimalarial agentsen_US
dc.typeJournal Articleen_US
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