Synthesis of some new spirocyclic β-lactam and spirocyclic thiazolidin-4-one derivatives

Elkanzi, Nadia A. A.; Yosef, Hisham Abdallah A.; Mohamed, Nesrin Mahmoud Morsy

doi:10.5155/eurjchem.4.3.195-202.777

Cited by 4 publications

(3 citation statements)

References 46 publications

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“…In an analogous approach, spiro-[chloroazetidinethiazolopyrimidine] derivatives were obtained by using the corresponding thiazolopyrimidine imines. 31…”

Section: Methodsmentioning

confidence: 99%

An update on the synthesis and reactivity of spiro-fused β-lactams

Thi¹,

D’hooghe²

2019

Arkivoc

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β-Lactam ring-containing compounds play a pivotal role in drug design and synthetic chemistry. Spirocyclic βlactams, representing an important β-lactam subclass, have recently attracted considerable interest with respect to new synthetic methodologies and pharmacological applications. The aim of this manuscript is to review the recent progress made in this field, covering publications disseminated between 2011 to 2018 concerning the synthesis and application of spirocyclic β-lactams. In the first part, new approaches to the synthesis of spirocyclic β-lactams, including Staudinger synthesis, cyclization and transformation reactions, will be presented. The reactivity and biological properties of spiro-β-lactams will be described in the second and third part, respectively.

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“…In an analogous approach, spiro-[chloroazetidinethiazolopyrimidine] derivatives were obtained by using the corresponding thiazolopyrimidine imines. 31…”

Section: Methodsmentioning

confidence: 99%

An update on the synthesis and reactivity of spiro-fused β-lactams

Thi¹,

D’hooghe²

2019

Arkivoc

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“…The search of convenient synthetic approaches for the construction of new compounds with potential biological and pharmacological effects is an extension of our efforts to find convenient synthetic approaches [48–60] . In connection with these aforesaid observations, the purpose of this study is to develop novel bioactive isolated spiro β ‐Lactam and thiazolidinone derivatives bearing 1,8‐naphthyridine moiety.…”

Section: Introductionmentioning

confidence: 99%

“…[47] The search of convenient synthetic approaches for the construction of new compounds with potential biological and pharmacological effects is an extension of our efforts to find convenient synthetic approaches. [48][49][50][51][52][53][54][55][56][57][58][59][60] In connection with these aforesaid observations, the purpose of this study is to develop novel bioactive isolated spiro β-Lactam and thiazolidinone derivatives bearing 1,8-naphthyridine moiety. The synthesized compounds were identified based on their spectral and elemental data, and were tested for their antioxidant and antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

Antioxidant and Antimicrobial Potential of 1,8‐Naphthyridine Based Scaffolds: Design, Synthesis and in Silico Simulation Studies within Topoisomerase II

Elkanzi,

Hrichi,

Muqbil Alsirhani

et al. 2024

Chemistry & Biodiversity

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A series of spiro β‐ Lactams (4a‐c, 7a‐c) and thiazolidinones (5a‐c, 8a‐c) possessing 1,8‐naphthyridine moiety were synthesized in this study. The structure of the newly synthesized compounds has been confirmed by IR, 1H NMR, 13C NMR mass spectra, and elemental analysis. The synthesized compounds were tested in vitro for their antibacterial and antifungal activity against various strains. The antimicrobial data showed that most of the compounds displayed good efficacy against both bacteria and fungi. The structure‐activity relationship (SAR) studies suggested that the presence of electron‐withdrawing chloro (3b, 4b, and 5b) and nitro groups (7b, 8b) at the para position of the phenyl ring improved the antimicrobial activity of the compounds. The free radical scavenging assay showed that all the synthesized compounds exhibited significant antioxidant activity on DPPH. Compounds 8b (IC50 = 17.68± 0.76 µg/mL) and 4c (IC50 =18.53±0.52 µg/mL) showed the highest antioxidant activity compared to ascorbic acid (IC50=15.16±0.43 µg/mL). Molecular docking studies were also conducted to support the antimicrobial and SAR results.

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Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

2015

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A variety of selenium compounds were proven to be useful reagents and catalysts for organic synthesis over the past several decades. The most interesting aspect, which emerged in recent years, concerns application of hydroperoxide/selenium(IV) oxide and hydroperoxide/organoselenium catalyst systems, as "green reagents" for the oxidation of different organic functional groups. The topic of oxidations catalyzed by organoselenium derivatives has rapidly expanded in the last fifteen years This paper is devoted to the synthetic applications of the oxidation reactions mediated by selenium compounds such as selenium(IV) oxide, areneseleninic acids, their anhydrides, selenides, diselenides, benzisoselenazol-3(2H)-ones and other less often used other organoselenium compounds. All these compounds have been successfully applied for various oxidations useful in practical organic syntheses such as epoxidation, 1,2-dihydroxylation, and α-oxyfunctionalization of alkenes, as well as for ring contraction of cycloalkanones, conversion of halomethyl, hydroxymethyl or active methylene groups into formyl groups, oxidation of carbonyl compounds into carboxylic acids and/or lactones, sulfides into sulfoxides, and secondary amines into nitrones and regeneration of parent carbonyl compounds from their azomethine derivatives. Other reactions such as dehydrogenation and aromatization, active carbon-carbon bond cleavage, oxidative amidation, bromolactonization and oxidation of bromide for subsequent reactions with alkenes are also successfully mediated by selenium (IV) oxide or organoselenium compounds. The oxidation mechanisms of ionic or free radical character depending on the substrate and oxidant are discussed. Coverage of the literature up to early OPEN ACCESSMolecules 2015, 20 10206 2015 is provided. Links have been made to reviews that summarize earlier literature and to the methods of preparation of organoselenium reagents and catalysts.

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Synthesis of some new spirocyclic β-lactam and spirocyclic thiazolidin-4-one derivatives

Cited by 4 publications

References 46 publications

An update on the synthesis and reactivity of spiro-fused β-lactams

An update on the synthesis and reactivity of spiro-fused β-lactams

Antioxidant and Antimicrobial Potential of 1,8‐Naphthyridine Based Scaffolds: Design, Synthesis and in Silico Simulation Studies within Topoisomerase II

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

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