8-Substituted 1,3-dimethyltetrahydropyrazino[2,1-f]purinediones: Water-soluble adenosine receptor antagonists and monoamine oxidase B inhibitors

Brunschweiger, Andreas; Koch, Pierre; Schlenk, Miriam; Rafehi, Muhammad; Radjainia, H.; Küppers, Petra; Hinz, Sonja; Pineda, Felipe; Wiese, Michael; Hockemeyer, Jörg; Heer, Jag; Denonne, Frédéric; Müller, Christian

doi:10.1016/j.bmc.2016.09.003

Cited by 23 publications

(21 citation statements)

References 44 publications

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“…Aminothiazoles derivatives as SUMOylation activators [124] AMN082 [115] Amodiaquine [125,126] Antagonist of the A(2A) adenosine receptor-derivative 49 [127] Apigenin [128][129][130][131] Apomorphine [132,133] l-Arginine [134] Aromadendrin [128] Ascorbic acid [135,136] ASI-1 [12] ASI-5 [12] Astilbin [137] Azilsartan [138] Baicalein [139][140][141] Benserazide [142,143] 7H-Benzo, perimidin-7-one derivatives (R6 = OH) [144] 4H-1-Benzopyran-4-one [145] 8-Benzyl-tetrahydropyrazino, purinedione derivatives (derivative n.57) [146] Bikaverin [147]…”

Section: Compound Name(s) Referencesmentioning

confidence: 99%

Metal Chelation Therapy and Parkinson’s Disease: A Critical Review on the Thermodynamics of Complex Formation between Relevant Metal Ions and Promising or Established Drugs

Tosato

Marco

2019

Biomolecules

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The present review reports a list of approximately 800 compounds which have been used, tested or proposed for Parkinson’s disease (PD) therapy in the year range 2014–2019 (April): name(s), chemical structure and references are given. Among these compounds, approximately 250 have possible or established metal-chelating properties towards Cu(II), Cu(I), Fe(III), Fe(II), Mn(II), and Zn(II), which are considered to be involved in metal dyshomeostasis during PD. Speciation information regarding the complexes formed by these ions and the 250 compounds has been collected or, if not experimentally available, has been estimated from similar molecules. Stoichiometries and stability constants of the complexes have been reported; values of the cologarithm of the concentration of free metal ion at equilibrium (pM), and of the dissociation constant Kd (both computed at pH = 7.4 and at total metal and ligand concentrations of 10–6 and 10–5 mol/L, respectively), charge and stoichiometry of the most abundant metal–ligand complexes existing at physiological conditions, have been obtained. A rigorous definition of the reported amounts is given, the possible usefulness of this data is described, and the need to characterize the metal–ligand speciation of PD drugs is underlined.

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Section: Compound Name(s) Referencesmentioning

confidence: 99%

Metal Chelation Therapy and Parkinson’s Disease: A Critical Review on the Thermodynamics of Complex Formation between Relevant Metal Ions and Promising or Established Drugs

Tosato

Marco

2019

Biomolecules

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“…The SAR revealed that tetrahydronaphthalene substitution has enabled the balanced potency better than other substitutions ( p‐ bromophenyl, m ‐bromophenyl, 4‐chloro‐2,2,2‐trifluoromethyl etc.) [168,169] …”

Section: Synthetic Approaches and Design Aspects Of Various Classes Omentioning

confidence: 99%

An Update of Synthetic Approaches and Structure‐Activity Relationships of Various Classes of Human MAO‐B Inhibitors

2021

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The selective MAO‐B inhibition is greatly influenced by the degradation pathways of various biogenic amines. So the design and development of diverse class of MAO‐B inhibitors are considered as an effective adjuvant therapy of various neurodegenerative disorders. Recent studies documented that introduction of an electron rich linker between two aryl or heteroaryl rings explored as a promising structural framework of the inhibition of MAO‐B. The electrophilicity and flexibility character of the linker can anchor different orientation of binding mode in both entrance and substrate cavity of MAO‐B. The current review focus on the design aspect, synthetic route and structure activity relationships (SARs) various class of selective MAO‐B inhibitors like chalcones, coumarins, chromones, pyrazolines, xanthines, isatins, FDA approved analogs etc.

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“…The known methods for the synthesis of 4‐(het)arylisoxazoles include palladium‐catalyzed C–C couplings,, , various heterocyclizations and recyclizations, diazotative deamination of the corresponding 5‐aminoisoxazoles, and formal [3+2] cycloaddition of alkynes, electron‐deficient enamines or their synthetic equivalents with halogenoximes , . The latter approach can be considered as the most convenient since generally, the target products are obtained in good yields with high regioselectivity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 4‐Hetarylisoxazoles from Amino Acid‐Derived Halogenoximes and Push‐Pull Enamines

et al. 2018

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An approach to 4‐hetarylisoxazole‐derived amines and other related 3,4‐disubstituted isoxazoles which relies on [3+2] cycloaddition of amino acid‐derived halogenoximes and push‐pull enamines is described. The target products are obtained at gram scale in up to 81 % overall yield. The efficiency of the method is affected by the electronic properties of the enamine component at the key step.

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8-Substituted 1,3-dimethyltetrahydropyrazino[2,1-f]purinediones: Water-soluble adenosine receptor antagonists and monoamine oxidase B inhibitors

Cited by 23 publications

References 44 publications

Metal Chelation Therapy and Parkinson’s Disease: A Critical Review on the Thermodynamics of Complex Formation between Relevant Metal Ions and Promising or Established Drugs

Metal Chelation Therapy and Parkinson’s Disease: A Critical Review on the Thermodynamics of Complex Formation between Relevant Metal Ions and Promising or Established Drugs

An Update of Synthetic Approaches and Structure‐Activity Relationships of Various Classes of Human MAO‐B Inhibitors

Synthesis of 4‐Hetarylisoxazoles from Amino Acid‐Derived Halogenoximes and Push‐Pull Enamines

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