Groebke Blackburn Bienaymé-mediated multi-component synthesis of selective HDAC6 inhibitors with anti-inflammatory properties

Kraft, Fabian B.; Enns, Jana; Honin, Irina; Engelhardt, Jonas; Schöler, Andrea; Smith, Shannon T.; Meiler, Jens; Schäker-Hübner, Linda; Weindl, Günther; Hansen, Finn K.

doi:10.1016/j.bioorg.2023.107072

Cited by 4 publications

(1 citation statement)

References 55 publications

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“…However, there are no studies employing 2D BCN as a catalyst for the multicomponent synthesis of fused heterocyclic compounds through a cyclization reaction. Imidazo[1,2-α]pyridines find an upper hand in the field of medicinal chemistry and they possess a wide range of biological activities including antibacterial, 1 anti-inflammatory, 2 antituberculosis, 3 and anticancer activities. 4 In addition, they are the potent inhibitors of gastric acid secretion, 5 GABAA receptor modulators, 6 and TRPM2-specific inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Frustrated Lewis pairs in two-dimensional borocarbonitride for the facile synthesis of 3-aminoimidazo[1,2-α]pyridines using TMSCN as an isonitrile substitute

Leng,

Ali,

Al-Lohedan

et al. 2024

New J. Chem.

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Section: Introductionmentioning

confidence: 99%

Frustrated Lewis pairs in two-dimensional borocarbonitride for the facile synthesis of 3-aminoimidazo[1,2-α]pyridines using TMSCN as an isonitrile substitute

Leng,

Ali,

Al-Lohedan

et al. 2024

New J. Chem.

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Micro-scale screening of genetically modified Fusarium fujikuroi strain extends the apicidin family

Fischle,

Lutsch,

Hübner

et al. 2024

Nat. Prod. Bioprospect.

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Apicidins are a class of naturally occurring cyclic tetrapeptides produced by few strains within the Fusarium genus. These secondary metabolites have gained significant attention due to their antiprotozoal activity through HDAC inhibition, thereby highlighting their potential for the treatment of malaria. Predominantly, apicidins have been isolated from Fusarium semitectum, offering a deep insight into the biosynthetic pathway responsible for their formation. A similar biosynthetic gene cluster has also been identified in the rice pathogenic fungus F. fujikuroi, leading the discovery of three additional apicidins through genetic manipulation. Routine mass spectrometric screening of these compound-producing strains revealed another metabolite structurally related to previously studied apicidins. By optimizing culture conditions and developing an effective isolation method, we obtained a highly pure substance, whose chemical structure was fully elucidated using NMR and HRMS fragmentation. Further studies were conducted to determine cytotoxicity, antimalarial activity, and HDAC inhibitory activity of this new secondary metabolite alongside the previously known apicidins. This work not only expands the apicidin class with a new member but also provides extensive insights and comparative analysis of apicidin-like substances produced by F. fujikuroi. Graphical Abstract

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Preferential HDAC6 inhibitors derived from HPOB exhibit synergistic antileukemia activity in combination with decitabine

Tretbar,

Schliehe-Diecks,

von Bredow

et al. 2024

European Journal of Medicinal Chemistry

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Groebke Blackburn Bienaymé-mediated multi-component synthesis of selective HDAC6 inhibitors with anti-inflammatory properties

Cited by 4 publications

References 55 publications

Frustrated Lewis pairs in two-dimensional borocarbonitride for the facile synthesis of 3-aminoimidazo[1,2-α]pyridines using TMSCN as an isonitrile substitute

Frustrated Lewis pairs in two-dimensional borocarbonitride for the facile synthesis of 3-aminoimidazo[1,2-α]pyridines using TMSCN as an isonitrile substitute

Micro-scale screening of genetically modified Fusarium fujikuroi strain extends the apicidin family

Preferential HDAC6 inhibitors derived from HPOB exhibit synergistic antileukemia activity in combination with decitabine

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