Fourfold symmetric MCR's <i>via</i> the tetraisocyanide 1,3-diisocyano-2,2-bis(isocyanomethyl)propane

Butera, Roberto; Shrinidhi, Annadka; Kurpiewska, Katarzyna; Kalinowska‐Tłuścik, Justyna; Dömling, Alexander

doi:10.1039/d0cc04522e

Cited by 4 publications

(4 citation statements)

References 19 publications

(31 reference statements)

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“…This interaction is assisted by the highly polarized nature of the CH group surrounded by the electronegative oxygen and nitrogens. The isocyanide 1,3-diisocyano-2,2-bis(isocyanomethyl)propane 16 is one of the very few known tetraisocyanides and features S 4 symmetry in solution . The well-described electronegativity of the isocyano group renders the α-mehylene CH group acidic, and the polarized CH group undergoes a hydrogen bond with the neighboring isocyano group of 2.6 Å and an angle (NCH) of 147°.…”

Section: Resultsmentioning

confidence: 99%

“…The isocyanide 1,3-diisocyano-2,2-bis(isocyanomethyl)propane 16 is one of the very few known tetraisocyanides and features S 4 symmetry in solution. 58 The well-described electronegativity of the isocyano group renders the α-mehylene CH group acidic, and the polarized CH group undergoes a hydrogen bond with the neighboring isocyano group of 2.6 Å and an angle (NCH) of 147°. Carbenes are isoelectronic to isocyandes, and they are considered to be in oxidation state C II .…”

Section: Resultsmentioning

confidence: 99%

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Crystal Clear: Decoding Isocyanide Intermolecular Interactions through Crystallography

Chatziorfanou,

Romero,

Chouchane

et al. 2024

J. Org. Chem.

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The isocyanide group is the chameleon among the functional groups in organic chemistry. Unlike other multiatom functional groups, where the electrophilic and nucleophilic moieties are typically separated, isocyanides combine both functionalities in the terminal carbon. This unique feature can be rationalized using the frontier orbital concept and has significant implications for its intermolecular interactions and the reactivity of the functional group. In this study, we perform a Cambridge Crystallographic Database-supported analysis of isocyanide intramolecular interactions to investigate the intramolecular interactions of isocyanides in the solid state, excluding isocyanide−metal complexes. We discuss examples of different interaction classes, including the isocyanide as a hydrogen bond acceptor (RNC•••HX), halogen bonding (RNC•••X), and interactions involving the isocyanide and carbon atoms (RNC•••C). The latter interaction serves as an intriguing illustration of a Burgi−Dunitz trajectory and represents a crucial experimental detail in the well-known multicomponent reactions such as the Ugi-and Passerini-type mechanisms. Understanding the spectrum of intramolecular interactions that isocyanides can undergo holds significant implications in fields such as medicinal chemistry, materials science, and asymmetric catalysis.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Crystal Clear: Decoding Isocyanide Intermolecular Interactions through Crystallography

Chatziorfanou,

Romero,

Chouchane

et al. 2024

J. Org. Chem.

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“…This reaction type was the modified Ugi reaction, and it was the first reported use of MCR in lipidoids synthesis. 92–99 Notably, the ethanol used in this reaction as well as the absence of catalysts are of great help in the high-throughput screening of ionizable lipids. The top-performing lipid formulations shared a common structure, which included an unsaturated lipid tail, cyclic amine headgroups, and a dihydroimidazole linker.…”

Section: Combinatorial Chemistry For Ionizable Lipidsmentioning

confidence: 99%

Rational design and combinatorial chemistry of ionizable lipids for RNA delivery

Xu¹,

Golubovic²,

Xu³

et al. 2023

J. Mater. Chem. B

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“…Authors recommend its use for clinical, regulatory, publication, and expert purposes to facilitate the valid establishment of causality in suspected cases of DILI and HILI. This updated version not only simplifies the handling of the criteria but also promotes an internationally harmonized approach to causality assessment, serving as a fundamental tool for practitioners in the field [88][89][90][91][92][93][94][95][96][97].…”

Section: Rucam In Drug and Herb Induced Liver Injurymentioning

confidence: 99%

Advancements in Drug Delivery Systems for Natural Compounds Targeting Metabolic Disorders Associated with Inflammation

Sam,

Neal

2023

Arch Gastroenterol Res

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The global incidence of metabolic disorders is on the rise, posing a significant challenge to public health. With remarkable advancements in diagnostic tools and clinical procedures, our understanding of the etiology and underlying pathophysiology of these disorders has expanded considerably. Furthermore, the utilization of in vitro and in vivo experimental models, preceding clinical investigations, has catalyzed numerous breakthroughs in biomedicine, particularly in the identification and development of potential drug candidates for the management of metabolic disorders. Natural compounds isolated from various sources have garnered extensive attention as prospective drug candidates for the treatment of conditions such as diabetes, obesity, heart-related diseases, and cancer. This interest is partly attributed to their inherent antioxidant and anti-inflammatory properties. Concurrently, intensive research efforts have been directed towards enhancing the bioactivity and bioavailability of these compounds through selected drug delivery strategies. In this article, we provide valuable insights into recent advancements that shed light on the role of inflammatory-mediated responses in the initiation of metabolic disorders, with a specific focus on conditions like diabetes mellitus, obesity, heart-related diseases, cancer, and related drug delivery systems. Additionally, we explore the promising potential of natural products in managing these metabolic disorders. Furthermore, we present lists of potential biological targets suitable for high throughput screening in the drug discovery and development process. Finally, we delve into the findings gleaned from preclinical and clinical studies, setting the stage for the identification of suitable approaches in the realm of phytochemical drug delivery systems that hold promise for the treatment of metabolic disorders.

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Fourfold symmetric MCR's via the tetraisocyanide 1,3-diisocyano-2,2-bis(isocyanomethyl)propane

Abstract: Oligoisocyanides are attractive synthetic targets, however, only a few are known. Here, we describe the smallest stable tetraisocyanide possible, the 1,3-diisocyano-2,2-bis(isocyano-methyl)propane (1) with S4 symmetry. Its synthesis, structure, and reactivity...

Cited by 4 publications

References 19 publications

Crystal Clear: Decoding Isocyanide Intermolecular Interactions through Crystallography

Crystal Clear: Decoding Isocyanide Intermolecular Interactions through Crystallography

Rational design and combinatorial chemistry of ionizable lipids for RNA delivery

Advancements in Drug Delivery Systems for Natural Compounds Targeting Metabolic Disorders Associated with Inflammation

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