Survey in Pyrrole Compounds and Biological Activity (original) (raw)
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Synthesis of Pyrrole and Substituted Pyrroles (Review)
2018
Pyrrole is widely known as a biologically active scaffold which possesses a diverse nature of activities. The combination of different pharmacophores in a pyrrole ring system has led to the formation of more active compounds. Pyrrole containing analogs are considered as a potential source of biologically active compounds that contains a significant set of advantageous properties and can be found in many natural products. The present review highlights the synthetic methods of representatives of nitrogen heterocycles such as pyrrole, substituted pyrroles and other related compounds. The aim of this review is to indicate and summarise the different methods for the synthesis of nitrogen containing heterocycles from the group of pyrrole and pyrrole related structures.
Recent synthetic and medicinal perspectives of pyrroles: An overview
2017
Pyrrole is a privileged scaffold with assorted nature of biological activities. Many active compounds have been developed by amalgamation of different pharmacophores in a pyrrole ring system. Pyrroles are an active component of complex macrocycles, including the porphyrins of heme, chlorins, bacteriochlorins, chlorophyll, porphyrinogens. Pyrrole and its derivatives are widely used as intermediates in synthesis of pharmaceuticals, agrochemicals, dyes, photographic chemicals, perfumes and other organic compounds. The pyrrole skeleton is an imperative structural framework found in extensive range of biologically active natural products and pharmaceutically active molecules. They are an element of polymers, indigoid dyes and large aromatic rings. Pyrroles are utilized as a catalyst for polymerization process, corrosion inhibitor, preservative, solvent for resins and terpenes. It is functional in various metallurgical process, luminescence chemistry, spectrochemical analysis and transiti...
A Novel Strategy for the Synthesis of 3-(N-Heteryl)pyrrole Derivatives
Organic Letters, 2012
A flexible approach to unknown 1-(1H-pyrrol-3-yl)pyridinium salts with selective control of the substitution patterns, by the reaction of pyridinium ylides with 2H-azirines, is disclosed. 3-(Pyridinium-1-yl)pyrrolides, a new type of stable ylide, were prepared from these salts in high yields by treatment with base. Atmospheric-pressure hydrogenation of the ylides with Adams' catalyst lead to 1-(pyrrol-3-yl)piperidines in good yields. Pyrrole is one of the most important simple heterocycles, whose structural unit is present in a large number of natural compounds, medical and material molecules. 1 By limiting ourselves to a short introduction it is impossible to reflect adequately the variety of chemistry and the value of pyrrole derivatives, so we will mention only recently published works in which the bioactivity of compounds containing 3-(pyridine-1-yl)pyrrole fragments were investigated, since compounds of this type are a subject of our research. The mentioned structural units are present in compounds which are antibacterial agents targeting DNA gyrase, 2 inhibitors of human DPP-4 for the treatment of type 2 diabetes, 3 NMDA receptor antagonists, 4 selective NK 1 antagonists, 5 and potent antagonists of VLA-4. 6 Although excellent preparative methods for the synthesis of substituted pyrroles have been developed, 1 it is still a great challenge to synthesize functionalized pyrroles from readily available and easily varied starting materials using a simple procedure. One such approach to the synthesis of pyrrole derivatives is based on the reactions of nucleophiles with 2H-azirines. The first example of reactions of 3-phenyl-2H-azirine with enolates leading to pyrrole derivatives was published by Sato. 7 2H-Pyrroles were prepared in good yields from 2H-azirines and enolates from activated
International Journal of Molecular Sciences
The current study describes the synthesis, physicochemical characterization and cytotoxicity evaluation of a new series of pyrrole derivatives in order to identify new bioactive molecules. The new pyrroles were obtained by reaction of benzimidazolium bromide derivatives with asymmetrical acetylenes in 1,2-epoxybutane under reflux through the Huisgen [3 + 2] cycloaddition of several ylide intermediates to the corresponding dipolarophiles. The intermediates salts were obtained from corresponding benzimidazole with bromoacetonitrile. The structures of the newly synthesized compounds were confirmed by elemental analysis, spectral techniques (i.e., IR, 1H-NMR and 13C-NMR) and single-crystal X-ray analysis. The cytotoxicity of the synthesized compounds was evaluated on plant cells (i.e., Triticum aestivum L.) and animal cells using aquatic crustaceans (i.e., Artemia franciscana Kellogg and Daphnia magna Straus). The potential antitumor activity of several of the pyrrole derivatives was st...
Synthesis, characterization and biological activity of novel pyrrole compounds
5-((1, 3-dioxoisoindolin-2-yl) methyl-2-hydroxybenzohydrazide (1) undergoes facile condensation with aromatic aldehydes to afford the corresponding N'-Substitutedphenyl-5-((1, 3-dioxoisoindolin-2-yl) methyl)-2-hydroxy benzo hydrazides (2a-h) in good yield. Cyclocondensation of compounds (2a-h) with maleic anhydride yields 1-(5-((1, 3dioxoisoindolin-2-yl) methyl)-2-hydroxybenzamido) -5-oxo-2-substituted phenyl-2, 5-dihydro-1H-pyrrole-3carboxylic acid (3a-h). The structures of these compounds were established on the basis of analytical and spectral data. All the newly synthesized compounds were evaluated for their antibacterial and antifungal activities.