Synthesis, biological evaluation, density functional calculation and molecular docking analysis of novel spiropyrrolizidines derivatives as potential anti-microbial and anti-coagulant agents

Askri, Sonia; Edziri, Hayet; Hamouda, Manel Ben; Mchiri, Chadlia; Gharbi, Rafik; El‐Gawad, Hala H. Abd; El‐Tahawy, Mohsen M. T.

doi:10.1016/j.molstruc.2021.131688

Cited by 9 publications

(6 citation statements)

References 48 publications

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“…To explain the stereochemical outcome in line with antecedent studies and our previous experimental findings [33][34][35][36][37][38][39][40][41], we propose in Scheme 4 a plausible mechanism for the regioselective and stereoselective formation of the spiro[oxindole-2,3′-pyridine].…”

Section: Mecanistic Discussionsupporting

confidence: 58%

“…Several succinimides are furthermore used as anticonvulsant drugs, including ethosuximide (Zarontin), phensuximide, and methsuximide (Petinutin) [31,32]. Recently, we showed that some spirooxindolepyrrolidine and spirooxindolepyrrolizidine derivatives incorporating the pyrrolidine-2,5-dione motif are promising for acetylcholinesterase (AChE) inhibition [33] and possess both antimicrobial and anticoagulant activities [34].…”

Section: This Work Dispiro[pyrrolidine-23'-oxindoles]mentioning

confidence: 99%

“…Herein, and in continuation of our research in the domain of one-pot MCRs of azomethine ylides [33][34][35][36][37][38][39][40][41], we report on the synthesis of various spiro[oxindole-2,3 -pyrrolidines] tethered with succinimide derivatives. The latter were assembled by a one-pot threecomponent [3+2]-cycloaddition reaction of isatin itself or halogenated isatin derivatives 1, L-valine 2 and (E)-3-arylidene-1-methyl-succinimides 4.…”

Section: This Work Dispiro[pyrrolidine-23'-oxindoles]mentioning

confidence: 99%

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Antimicrobial Activity and In Silico Molecular Docking Studies of Pentacyclic Spiro[oxindole-2,3′-pyrrolidines] Tethered with Succinimide Scaffolds

et al. 2021

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Three-component cascade reactions of (E)-3-arylidene-1-methyl-pyrrolidine-2,5-diones, L-valine and various isatin derivatives are described. A series of 17 spiropyrrolidine derivatives with wide structural complexity and diversity have been thus obtained in moderate to excellent yields under mild reaction conditions. The structure and stereochemistry of these N-heterocyclic cycloadducts has been established by spectroscopic techniques and unambiguously confirmed by a single-crystal X-ray diffraction analysis performed on one derivative. UV-visible spectra have been recorded for all new compounds. Furthermore, the synthesized N-heterocyclic compounds have been screened for their in vitro antibacterial and antifungal activities. Several derivatives exhibited moderate to good activities, comparable to those of the known standard drugs Amphotericin B and Tetracycline. Structural activity relationships (SARs) and molecular docking of the most promising derivatives into the binding sites of glucosamine 6-phosphate synthase (GlcN6P) and methionyl-trna-synthetase (1PFV) were also established. Furthermore, pharmacokinetic studies indicate that the heterocycles exhibit acceptable predictive ADMET (absorption, distribution, metabolism, excretion, and toxicity) properties and good drug ability.

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Section: Mecanistic Discussionsupporting

confidence: 58%

Section: This Work Dispiro[pyrrolidine-23'-oxindoles]mentioning

confidence: 99%

Section: This Work Dispiro[pyrrolidine-23'-oxindoles]mentioning

confidence: 99%

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Antimicrobial Activity and In Silico Molecular Docking Studies of Pentacyclic Spiro[oxindole-2,3′-pyrrolidines] Tethered with Succinimide Scaffolds

et al. 2021

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“…Similar to Bekhradnia's reaction, El-Tahawy and co-workers employed 3-arylidene-1-methyl-pyrrolidine-2,5-diones as a dipolarophile in the reaction with isatins and l -proline to form spiro-oxindolopyrrolizidines. 38 In this method, the cyclization reactions were performed in MeOH as the solvent under reflux conditions. They could also report anti-microbial and anti-coagulant properties of these spiro products in the range of moderate to strong activity.…”

Section: 3-dipolar Cycloadditions For Synthesis Of Spiro-heterocyclesmentioning

confidence: 99%

Decarboxylative 1,3-dipolar cycloadditions of l-proline

Doraghi,

Serajian,

Karimian

et al. 2024

RSC Adv.

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“…Another advantage of in silico is that it can fill data gaps in chemical risk assessments [15]. Some in silico models today are molecular docking and molecular dynamics simulations [16][17]. Some of the software used for molecular docking will be shown in this review, along with the PDB code for the anticoagulant protein used.…”

Section: ■ Introductionmentioning

confidence: 99%

A Deep Overview of Anticoagulant Drugs: Recent Synthesis and Their Activity Assay

Astuti,

Ibrahim,

Zulfikar

et al. 2024

Indones. J. Chem.

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During the unprecedented COVID-19 pandemic, anticoagulant drugs have emerged as a crucial component of treatment alongside antivirus medications. Patients with severe COVID-19 frequently have critical conditions marked by blood clot development, necessitating the administration of anticoagulants. This review aims to provide a comprehensive overview of various anticoagulant drugs, their synthesis methods, and assays employed to predict their anticoagulant activity. Notable anticoagulant categories frequently utilized include oral anticoagulants heparin, non-vitamin K antagonists, and vitamin K antagonists. In recent years, the development of new anticoagulants has seen a shift towards a multifaceted approach that combines in silico prediction with in vitro and in vivo assays. In silico prediction techniques play a pivotal role in the initial screening process. This integrated approach has yielded promising results, paving the way for the synthesis of novel anticoagulant candidates, as substantiated by a battery of in vitro, in vivo, and ex-vivo tests.

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Synthesis, biological evaluation, density functional calculation and molecular docking analysis of novel spiropyrrolizidines derivatives as potential anti-microbial and anti-coagulant agents

Cited by 9 publications

References 48 publications

Antimicrobial Activity and In Silico Molecular Docking Studies of Pentacyclic Spiro[oxindole-2,3′-pyrrolidines] Tethered with Succinimide Scaffolds

Antimicrobial Activity and In Silico Molecular Docking Studies of Pentacyclic Spiro[oxindole-2,3′-pyrrolidines] Tethered with Succinimide Scaffolds

Decarboxylative 1,3-dipolar cycloadditions of l-proline

A Deep Overview of Anticoagulant Drugs: Recent Synthesis and Their Activity Assay

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