Inhibition of peroxidase-catalyzed iodination by thioamides: experimental and theoretical study of the antithyroid activity of thioamides

Corban, Ghada J.; Hadjikakou, Sotiris K.; Tsipis, Athanasios C.; Kubicki, Maciej; Bakas, Thomas; Hadjiliadis, Nick

doi:10.1039/c0nj00626b

Cited by 32 publications

(15 citation statements)

References 44 publications

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“…Perhaps the most prominent crystal engineering piece of information that we can derive from the present study is the possibility to use charged azacyclophanes as templating agents for the synthesis of polyiodides. Despite some of this being reported for linear polyiodides (I3 − , I4 2− , I6 2− ) in the case of aliphatic [11] or aromatic [6] linear ammonium derivatives, in the current case we appear to be in the presence of the first three-dimensional mold reported for the synthesis of the I7 − anion, moreover a species which can be considered of quite rare occurrence (only 10 structures reported so far in the CSD feature I7 − [29][30][31][32][33][34][35][36][37][38], only half of them containing selectively I7 − rather than a mixture of As can be seen, the hydrophilic face of the azacyclophanes presenting the ammonium groups is found interacting either with a triiodide or with the iodine molecule strongly bound to a triiodide within the pentaiodide anion. Neither convergence of ammonium groups towards a specific anionic site, nor the encapsulation induced by the perfect fit observed in Figure 1 are possible here.…”

Section: Discussioncontrasting

confidence: 69%

Stabilization of Supramolecular Networks of Polyiodides with Protonated Small Tetra-azacyclophanes

et al. 2019

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Polyiodide chemistry is among the first historically reported examples of supramolecular forces at work. To date, owing to the increasingly recognized role of halogen bonding and the incorporation of iodine-based components in several devices, it remains an active field of theoretical and applied research. Herein we re-examine azacyclophanes as a class of ligands for the stabilization of iodine-dense three-dimensional networks, showing how we devised novel possible strategies starting from literature material. The new set of azacyclophane ligands affords novel crystal structures possessing intriguing properties, which develop on a double layer. At a macroscopic level, the obtained networks possess a very high iodine packing density (less than 2 times more diluted than crystalline I2): a simple parameter, IN, is also introduced to quickly measure and compare iodine packing density in different crystals. On the microscopic level, the present study provides evidence about the ability of one of the ligands to act as a three-dimensional supramolecular mold for the template synthesis of the rarely observed heptaiodide (I7−) anion. Therefore, we believe our approach and strategy might be relevant for crystal engineering purposes.

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Section: Discussioncontrasting

confidence: 69%

Stabilization of Supramolecular Networks of Polyiodides with Protonated Small Tetra-azacyclophanes

et al. 2019

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“…Thioamides exhibit wide range of biological properties such as antifungal [1], antioxidant [2,3] and anticonvulsant [4] activities. Some of them strongly inhibit phosphoglycerate dehydrogenase [5].…”

Section: Introductionmentioning

confidence: 99%

Progress in intermolecular and intramolecular reactions of thioamides with diazo compounds and azides

Бакулев

Shafran

Dehaen

2019

Tetrahedron Letters

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Reactions of thioamides with nitrogen-rich 1,3-dipoles, diazo compounds and azides, have been known for long time already. However in recent years introduction of catalysts of different types (rhodium-, ruthenium-and copper-containing and Lewis acids) as well as highly electrophilic sulfonyl azides, allowed the development of new methods for the synthesis of heterocycles, enamines and N-sulfonyl amidines. Moreover, a new methodology in organic synthesis, based on generation and subsequent transformations of a-diazocarbonyl compounds was created. Reactions of sulfonyl azides with thioamides undergo readily in mild conditions to produce different sorts of N-sulfonyl amidines and represent a new type of click-type processes. Most of the cited works were published in the current decade. Earlier seminal papers are also reviewed when they constitute the background for new synthetic methods which were developed further.

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“…What does this look like for our case study? Figure 8 provides a Baumkuchen model of the thyroid hormone formation and its action in the human body [5,23,26,27,[30][31][32][33]. As such, Figure 8 is effectively a revamped and more precise version of Figure 6.…”

Section: Constructing Baumkuchen (Spite Cake) Modelsmentioning

confidence: 99%

Disambiguating “Mechanisms” in Pharmacy: Lessons from Mechanist Philosophy of Science

Abdin

Jacob

Kästner

2020

IJERPH

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Talk of mechanisms is ubiquitous in the natural sciences. Interdisciplinary fields such as biochemistry and pharmacy frequently discuss mechanisms with the assistance of diagrams. Such diagrams usually depict entities as structures or boxes and activities or interactions as arrows. While some of these arrows may indicate causal or componential relations, others may represent temporal or operational orders. Importantly, what kind of relation an arrow represents may not only vary with context but also be underdetermined by empirical data. In this manuscript, we investigate how an analysis of pharmacological mechanisms in terms of producing and underlying mechanisms—as discussed in the contemporary philosophy of science—may shed light on these issues. Specifically, we shall argue that while pharmacokinetic mechanisms usually describe causal chains of production, pharmacodynamics tends to focus on mechanisms of action underlying the in vivo effects of a drug. Considering the action of thyroid gland hormones in the human body as a case study, we further demonstrate that pharmacodynamic schemes tend to incorporate entities and interactions on multiple levels. Yet, traditional pharmacodynamic schemes are sketched “flat”, i.e., non-hierarchically. We suggest that transforming flat pharmacodynamic schemes into mechanistic multi-level representations may assist in disentangling the different kinds of mechanisms and relations depicted by arrows in flat schemes. The resulting Baumkuchen model provides a powerful and practical alternative to traditional flat schemes, as it explicates the relevant mechanisms and relations more clearly. On a more general note, our discussion demonstrates how pharmacology and related disciplines may benefit from applying concepts from the new mechanist philosophy to guide the interpretation of scientific diagrams.

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Inhibition of peroxidase-catalyzed iodination by thioamides: experimental and theoretical study of the antithyroid activity of thioamides

Cited by 32 publications

References 44 publications

Stabilization of Supramolecular Networks of Polyiodides with Protonated Small Tetra-azacyclophanes

Stabilization of Supramolecular Networks of Polyiodides with Protonated Small Tetra-azacyclophanes

Progress in intermolecular and intramolecular reactions of thioamides with diazo compounds and azides

Disambiguating “Mechanisms” in Pharmacy: Lessons from Mechanist Philosophy of Science

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