Synthesis, anticonvulsant, and antinociceptive activity of new 3‐(3‐methyl‐2,5‐dioxo‐3‐phenylpyrrolidin‐1‐yl)propanamides and 3‐phenyl‐butanamides

Obniska, Jolanta; Góra, Małgorzata; Rapacz, Anna; Sałat, Kinga; Rybka, Sabina; Abram, Michał; Jakubiec, Marcin; Kamiński, Krzysztof

doi:10.1002/ardp.202000225

Cited by 5 publications

(2 citation statements)

References 54 publications

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“…Later, Obniska et al [ 59 ] expanded the same class of pyrrolidine-2,5-diones by substituting the thiophene ring with an unsubstituted phenyl moiety. The new compounds 66a–m (Fig.…”

Section: Pyrrolidine Derivatives Obtained By Ring Synthesismentioning

confidence: 99%

Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds

et al. 2021

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The five-membered pyrrolidine ring is one of the nitrogen heterocycles used widely by medicinal chemists to obtain compounds for the treatment of human diseases. The great interest in this saturated scaffold is enhanced by (1) the possibility to efficiently explore the pharmacophore space due to sp3-hybridization, (2) the contribution to the stereochemistry of the molecule, (3) and the increased three-dimensional (3D) coverage due to the non-planarity of the ring—a phenomenon called “pseudorotation”. In this review, we report bioactive molecules with target selectivity characterized by the pyrrolidine ring and its derivatives, including pyrrolizines, pyrrolidine-2-one, pyrrolidine-2,5-diones and prolinol described in the literature from 2015 to date. After a comparison of the physicochemical parameters of pyrrolidine with the parent aromatic pyrrole and cyclopentane, we investigate the influence of steric factors on biological activity, also describing the structure–activity relationship (SAR) of the studied compounds. To aid the reader’s approach to reading the manuscript, we have planned the review on the basis of the synthetic strategies used: (1) ring construction from different cyclic or acyclic precursors, reporting the synthesis and the reaction conditions, or (2) functionalization of preformed pyrrolidine rings, e.g., proline derivatives. Since one of the most significant features of the pyrrolidine ring is the stereogenicity of carbons, we highlight how the different stereoisomers and the spatial orientation of substituents can lead to a different biological profile of drug candidates, due to the different binding mode to enantioselective proteins. We believe that this work can guide medicinal chemists to the best approach in the design of new pyrrolidine compounds with different biological profiles.

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“…Later, Obniska et al [ 59 ] expanded the same class of pyrrolidine-2,5-diones by substituting the thiophene ring with an unsubstituted phenyl moiety. The new compounds 66a–m (Fig.…”

Section: Pyrrolidine Derivatives Obtained By Ring Synthesismentioning

confidence: 99%

Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds

et al. 2021

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“…It is known that disubstituted piperazines can exhibit a wide range of pharmacological activity; they can act as anticonvulsant, 17 antifungal, 18 antiviral, 19 radioprotective, 20 antibacterial and antimalarial 21,22 agents. Accordingly, our studies in this field have shown that piperazine derivatives of pyrano [3,4-c]pyridines display high antibacterial 23 and neurotropic activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel 1,2,3-triazole-based hybrids via click reactions

Sirakanyan¹,

Ghochikyan²,

Spinelli³

et al. 2021

Arkivoc

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1,2,3-Triazoles have attracted the interest of researchers due to their wide range of biological activities which include antitumor, anti-leishmanial, bioluminescent and fungicidal activities This paper describes the synthesis of novel triazole hybrids containing biologically active fragments through cycloaddition (click) reactions, with the aim of increasing the diversity of known and active 1,2,3-triazole derivatives. All new compounds have been characterized by physicochemical methods.

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Reactive metabolites of the anticonvulsant drugs and approaches to minimize the adverse drug reaction

Pal¹,

Singh²,

Khan³

et al. 2021

European Journal of Medicinal Chemistry

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Synthesis, anticonvulsant, and antinociceptive activity of new 3‐(3‐methyl‐2,5‐dioxo‐3‐phenylpyrrolidin‐1‐yl)propanamides and 3‐phenyl‐butanamides

Cited by 5 publications

References 54 publications

Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds

Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds

Synthesis of novel 1,2,3-triazole-based hybrids via click reactions

Reactive metabolites of the anticonvulsant drugs and approaches to minimize the adverse drug reaction

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