Synthesis and pharmacological properties of polysubstituted 2-amino-4H-pyran-3-carbonitrile derivatives

Tashrifi, Zahra; Mohammadi‐Khanaposhtani, Mohammad; Hamedifar, Haleh; Larijani, Bagher; Ansari, Sara; Mahdavi, Mohammad

doi:10.1007/s11030-019-09994-9

Cited by 44 publications

(20 citation statements)

References 113 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This reaction was performed under classical reaction conditions described in the literature to prepare 2-amino-3-cyano-4 H -pyrans [ 27 ]. Thus, using an excess of malononitrile, in the presence of a catalytic amount of DBU, at 100 °C under MW irradiation for 30 min, the desired 4 H -pyran-fused BoOMe compound 6 was obtained in 64% yield ( Scheme 5 ), although there were still traces of starting material 3b in the crude reaction media.…”

Section: Resultsmentioning

confidence: 99%

Decoration of A-Ring of a Lupane-Type Triterpenoid with Different Oxygen and Nitrogen Heterocycles

et al. 2022

View full text Add to dashboard Cite

Betulinic acid (BA) was used as starting building block to create a library of novel BA-derived compounds containing O- and N-heterocycles. Firstly, BA was converted into methyl betulonate (BoOMe), which was used as intermediate in the developed methodologies. 1,2-Oxazine-fused BoOMe compounds were obtained in 12–25% global yields through a Michael addition of nitromethane to methyl (E)-2-benzylidenebetulonate derivatives, followed by nitro group reduction and intramolecular cyclization. Remarkably, the triterpene acts as a diastereoselective inducer in the conjugate addition of nitromethane, originating only one diastereomer out of four possible ones. Furthermore, other oxygen and nitrogen-containing heterocycles were installed at the A-ring of BoOMe, affording 2-amino-3-cyano-4H-pyran-fused BoOMe, diarylpyridine-fused BoOMe and 1,2,3-triazole–BoOMe compounds, using simple and straightforward synthetic methodologies. Finally, BA was revealed to be a versatile starting material, allowing the creation of a molecular diversification of compounds containing a triterpenic scaffold and O- and N-heterocycles.

show abstract

Section: Resultsmentioning

confidence: 99%

Decoration of A-Ring of a Lupane-Type Triterpenoid with Different Oxygen and Nitrogen Heterocycles

et al. 2022

View full text Add to dashboard Cite

show abstract

“…It is equalized by adding drops of concentrated hydrochloric acid HCl and noting the product's precipitation. The precipitate is separated by filtering, washed with cold water, and recrystallized methanol, and table (1) shows some physical properties of 2-amino-pyrene derivatives (I25-I32).…”

Section: Preparation Of 2-amino-pyran Derivatives (I33-i40) [24]mentioning

confidence: 99%

“…Pyrene or pyran is a heterocyclic, unsaturated organic compound consisting of six central atoms, five of which are carbon atoms and one oxygen atom, and contains two double bonds. It has the chemical formula C5H6O, and the molar mass is 82.10 g/mol [1]. Its common name is (IUPAC) 2H-Pyran, 4H-Pyran, and its other names are 2H-Oxine and 4H-Oxine [2].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization of ‎2-amino-pyran ‎and derivatives evaluation of the bacterial, ‎antioxidant and anticancer activity

Hamid

Attia

2022

ijhs

View full text Add to dashboard Cite

Using ethanol as a solvent, heterocyclic hexagonal rings for 2-amino-pyran derivatives (I33-I40) were produced by reacting a mole of chalcones derivatives with a mole of malononitrile. Physical properties such as melting point, colour, and molecular weight and spectroscopic measurements such as the infrared spectrum, [1H-NMR], [13C-NMR] spectrum were used to confirm the accuracy of the prepared compounds' compositions. The biological activity of various produced compounds was investigated in two species of pathogenic bacteria, one of which is Gram-positive, Staphylococcus aureus, and the other, Gram-negative, Escherichia coli. Chemical solutions for the two substances (I25, I32) with concentrations (0,01, 0.001, 0.0001) mg /ml were created using a solvent DMSO and Multer Hinton Agar growth medium. The antibiotic Ciprofloxacin was utilized as a control sample for the diffusion sensitivity test of the bacterial isolates used in the investigation. Using DPPH root and varied concentrations, the impact of chemical (I32) on the elimination of free radicals was also investigated. Breast cancer cells were taken from Baghdad's Medical City and used to test the efficiency of several produced chemicals against them.

show abstract

“…2-Amino-4H-pyran derivatives are recognized as a domineering category of compounds that are mostly deployed in pigments and cosmetics and also as potentially biodegradable agrochemicals. 119 Besides that, functionalized 4H-pyrans comprise a building unit of several naturally occurring products and biologically active molecules that enjoy assorted pharmacological activities, namely, antitumor 120 and antibacterial. 121 As a result, several synthetic routes and catalytic systems have been introduced in recent years.…”

Section: ■ Gold Np-catalyzed Mcrsmentioning

confidence: 99%

Gold Nanoparticle-Catalyzed Multicomponent Reactions

Yazdani

Hooshmand

Varma

2021

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

Nanotechnology and nanoscience hold great promise for many multidisciplinary applications, including catalysis where gold nanoparticles (GNPs) are considered "safer and environmentally benign" on account of the fact that they are relatively nontoxic and efficient for pivotal applications in natural-product synthesis, organic reactions, pharmaceutical industry, and medicinal chemistry. Since the physicochemical characteristics of GNPs pertain to their shape, size, composition, and surface modification, these features contribute to the reactivity and toxicity of nanomaterials in the catalytic systems. Multicomponent reactions (MCRs) lead to expeditious synthesis of biologically active molecules and active pharmaceutical ingredients (APIs) with atom economy and high efficiency, as well as a low E-factor, and they can be performed in one-pot operations deploying three or more reactants. Thus, applications of GNPs as robust catalysts in MCRs comprise an effective synthetic route with an ideal combination for the augmentation of greener and sustainable methods. Accordingly, cutting-edge examples of gold nanoparticle-catalyzed multicomponent reactions leading to a diverse range of valuable organic molecules such as isoxazolines, propargylamines, 3,4dihydropyrimidin-2(1H)-ones, pyrans, chromeno[2,3-d]pyrimidins, pyridines, and benzodiazepines are discussed and highlighted.

show abstract

Synthesis and pharmacological properties of polysubstituted 2-amino-4H-pyran-3-carbonitrile derivatives

Cited by 44 publications

References 113 publications

Decoration of A-Ring of a Lupane-Type Triterpenoid with Different Oxygen and Nitrogen Heterocycles

Decoration of A-Ring of a Lupane-Type Triterpenoid with Different Oxygen and Nitrogen Heterocycles

Synthesis, characterization of ‎2-amino-pyran ‎and derivatives evaluation of the bacterial, ‎antioxidant and anticancer activity

Gold Nanoparticle-Catalyzed Multicomponent Reactions

Contact Info

Product

Resources

About