Piperidine nucleus in the field of drug discovery

Background Piperidine is an essential heterocyclic system and a pivotal cornerstone in the production of drugs. Piperidine byproducts showed several important pharmacophoric features and are being utilized in different therapeutic applications. Main text Piperidine derivatives are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents. Conclusions This review article sheds a light on the most recent studies proving the importance of piperidine nucleus in the field of drug discovery.

Disazo (Bishydrazone) pigments based on pyrazolones

The most important classical orange organic pigments are disazopyrazolones, also referred to as diarylide oranges. The first pigment in this series, CI Pigment Orange 13, was discovered in 1910 although it was a further 20 years before it was introduced as a commercial product. Currently, two orange disazopyrazolones are extremely important industrial organic pigments, while two red products are of lesser importance. The products are structurally analogous to the disazoacetoacetanilides (diarylide yellows), which are discussed in a separate chapter. For example, they are symmetrical compounds that exist in the bis-ketohydrazone tautomeric form. The pigments also exhibit similar technical and color properties compared with disazoacetoacetanilide pigments, for example providing high color strength and transparency, features that determine their importance as printing ink pigments. They are manufactured in a process that parallels those used for the disazoacetoacetanilide (diarylide) yellows, but with coupling components containing the pyrazolone heterocyclic system, in place of acetoacetanilides.

Heptazine-Based π-Conjugated Materials for Light-Emitting

On the basis of planar and relatively rigid nitrogen-rich heterocyclic system of the heptazine core, heptazine-based π-conjugated materials have aroused widespread attention over the past decade by virtue of the fascinating electronic, optical, thermal, and mechanical properties in the fields of light-emitting, photocatalysis, sensors, environmental remediation, and so forth. However, there are still several obstacles to be solved before practical applications, such as low photoluminescence quantum efficiencies for light-emitting and weak visible absorption for photocatalysis. To further enhance various properties of heptazine-based π-conjugated materials, a series of strategies have been developed, including ingenious molecular design and modification, novel synthetic, and preparation methods. In this review, the significant progress of monomeric and polymeric heptazine-based π-conjugated materials and their applications typically in light-emitting are reviewed, which is beneficial for the acceleration of practical applications of heptazine-based materials and devices.

7-Bromo-[1,2,5]selenadiazolo[3,4-d]pyridazin-4(5H)-one

New heterocyclic systems containing 1,2,5-chalcogenadiazoles are of great interest for the creation of organic photovoltaic materials and biologically active compounds. In this communication, 3,6-dibromopyridazine-4,5-diamine was investigated in reaction with selenium dioxide in order to obtain 4,7-dibromo-[1,2,5]selenadiazolo[3,4-d]pyridazine. We found that 7-bromo-[1,2,5]selenadiazolo[3,4-d]pyridazin-4(5H)-one, the first representative of the new heterocyclic system, was isolated as a hydrolysis product of the corresponding 4,7-dibromoderivative. The structure of the newly synthesized compound was established by means of elemental analysis, high-resolution mass spectrometry, 1H, 13C NMR, IR and UV spectroscopy, and mass spectrometry.

(E)-3-((2-Fluorophenyl)(hydroxy)methylene)imidazo[1,2-a]pyri-din-2(3H)-one

Treatment of a N-2-pyridyl-β-ketoamide precursor with bromine afforded the first example of the 3-aryl(α-hydroxy)methylenelimidazo[1,2-a]pyridin-2(3H)-one framework. This transformation proceeded through a domino process comprising an initial bromination, cyclization via an intramolecular SN reaction, and a final keto-enol tautomerism, and allows generation of the fused heterocyclic system and installation of the acyl substituent in a single operation.

Synergistic Cytotoxicity Between Cold Atmospheric Plasma and Pyrazolopyrimidinones Against Glioblastoma Cells

Pyrazolopyrimidinone is a fused nitrogen-containing heterocyclic system, which acts as a core scaffold in many pharmaceutically relevant compounds. Pyrazolopyrimidinones have been demonstrated to be efficient in treating several diseases, including cystic fibrosis, obesity, viral infection and cancer. We have tested the synergistic anti-cancer effects of 15 pyrazolopyrimidinones, synthesised in a two-step process, combined with cold atmospheric plasma (CAP), a novel innovation generating reactive species with other unique chemical and physical effects. We identify two pyrazolopyrimidinones that act as prodrugs and display enhanced reactive-species dependent cytotoxicity when used in combination with cold atmospheric plasma. Synergistic activation was evident for both direct CAP treatment on prodrug loaded tumour cells and indirect CAP treatment of prodrug in media prior to adding to tumour cells. Our results demonstrate the potential of CAP combined with pyrazolopyrimidinones as a programmable cytotoxic therapy against cancer.

Spirocyclic Nitroxides as Versatile Tools in Modern Natural Sciences: From Synthesis to Applications. Part I. Old and New Synthetic Approaches to Spirocyclic Nitroxyl Radicals

Spirocyclic nitroxyl radicals (SNRs) are stable paramagnetics bearing spiro-junction at α-, β-, or γ-carbon atom of the nitroxide fragment, which is part of the heterocyclic system. Despite the fact that the first representatives of SNRs were obtained about 50 years ago, the methodology of their synthesis and their usage in chemistry and biochemical applications have begun to develop rapidly only in the last two decades. Due to the presence of spiro-function in the SNRs molecules, the latter have increased stability to various reducing agents (including biogenic ones), while the structures of the biradicals (SNBRs) comprises a rigid spiro-fused core that fixes mutual position and orientation of nitroxide moieties that favors their use in dynamic nuclear polarization (DNP) experiments. This first review on SNRs will give a glance at various strategies for the synthesis of spiro-substituted, mono-, and bis-nitroxides on the base of six-membered (piperidine, 1,2,3,4-tetrahydroquinoline, 9,9′(10H,10H′)-spirobiacridine, piperazine, and morpholine) or five-membered (2,5-dihydro-1H-pyrrole, pyrrolidine, 2,5-dihydro-1H-imidazole, 4,5-dihydro-1H-imidazole, imidazolidine, and oxazolidine) heterocyclic cores.

Electrochemically Produced Copolymers of Pyrrole and Its Derivatives: A Plentitude of Material Properties Using “Simple” Heterocyclic Co-Monomers

Polypyrrole is a classical, well-known conjugated polymer that is produced from a simple heterocyclic system. Numerous pyrrole derivatives exhibit biological activity, and the repeat unit is a common building block present in the chemical structure of many polymeric materials, finding wide application, primarily in optoelectronics and sensing. In this work, we focus on the variety of copolymers and their material properties that can be produced electrochemically, even though all these systems are obtained from mixtures of the “simple” pyrrole monomer and its derivatives with different conjugated and non-conjugated species.