Synthesis and biological activity of 4-aryl-3-benzoyl-5-phenylspiro[pyrrolidine-2.3′-indolin]-2′-one derivatives as novel potent inhibitors of advanced glycation end product

Kaur, Anjandeep; Singh, Baldev; Vyas, Bhawna; Silakari, Om

doi:10.1016/j.ejmech.2014.04.022

Cited by 32 publications

(6 citation statements)

References 55 publications

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“…Few of the synthesized spiro-analogs 59 revealed potent inhibitory advanced glycation end (AGE) product formation in a bovine serum albumin (BSA)-glucose assay that was higher than that of aminoguanidine (standard reference). The occurrence of AGE is related to hyperglycemia observed as a complication of diabetes ( Scheme 18 ) [ 39 ].…”

Section: Acyclic Unsaturated 2π-electron Componentsmentioning

confidence: 99%

Azomethine Ylides—Versatile Synthons for Pyrrolidinyl-Heterocyclic Compounds

et al. 2023

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Azomethine ylides are nitrogen-based three-atom components commonly used in [3+2]-cycloaddition reactions with various unsaturated 2π-electron components. These reactions are highly regio- and stereoselective and have attracted the attention of organic chemists with respect to the construction of diverse heterocycles potentially bearing four new contiguous stereogenic centers. This review article complies the most important [3+2]-cycloaddition reactions of azomethine ylides with various olefinic, unsaturated 2π-electron components (acyclic, alicyclic, heterocyclic, and exocyclic ones) reported over the past two decades.

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Section: Acyclic Unsaturated 2π-electron Componentsmentioning

confidence: 99%

Azomethine Ylides—Versatile Synthons for Pyrrolidinyl-Heterocyclic Compounds

et al. 2023

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“…The 3,3’-spiropyrrolidinyloxindole unit is found in the molecular skeleton of a large family of natural alkaloids with remarkable bioactivity profiles and interesting structural properties [19–20]. Derivatives with the 2,3’-spiropyrrolidinyloxindole core show various biological effects such as bactericidal and fungicidal [21], anticancer [22], cytotoxic to MCF-7 and HepG2 cells [23–24], and advanced glycation end (AGE) product formation inhibitory activities [25] (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy

Izmest’ev

Газиева

Sigay

et al. 2016

Beilstein J. Org. Chem.

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An effective and highly regio- and diastereoselective one-pot method for the synthesis of new polynuclear dispiroheterocyclic systems with five stereogenic centers (dispiro[imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-6,3′-pyrrolidine-2′,3′′-indoles]) comprising pyrrolidinyloxindole and imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine moieties has been developed. The method relies on a 1,3-dipolar cycloaddition of azomethine ylides generated in situ from isatin derivatives and sarcosine to 6-benzylideneimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7-diones.

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“…Some of the synthesized agents revealed AGE (advanced glycation end, which is the formation of sugar-derived substances) inhibitory properties in the BSA (bovine serum albumin) glucose assay, supporting the suitability for diabetes. The most promising agent synthesized is that with R = Ph (IC 50 = 11.37 μM) relative to the aminoguanidine “standard reference” (IC 50 = 40.54 μM) [ 70 ].…”

Section: Synthetic Spirooxindolesmentioning

confidence: 99%

Spirooxindole: A Versatile Biologically Active Heterocyclic Scaffold

et al. 2023

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Spirooxindoles occupy an important place in heterocyclic chemistry. Many natural spirooxindole-containing compounds have been identified as bio-promising agents. Synthetic analogs have also been synthesized utilizing different pathways. The present article summarizes the recent development of both natural and synthetic spirooxindole-containing compounds prepared from isatin or its derivatives reported in the last five years. The spirooxindoles are categorized based on their mentioned biological properties.

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Synthesis and biological activity of 4-aryl-3-benzoyl-5-phenylspiro[pyrrolidine-2.3′-indolin]-2′-one derivatives as novel potent inhibitors of advanced glycation end product

Cited by 32 publications

References 55 publications

Azomethine Ylides—Versatile Synthons for Pyrrolidinyl-Heterocyclic Compounds

Azomethine Ylides—Versatile Synthons for Pyrrolidinyl-Heterocyclic Compounds

An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy

Spirooxindole: A Versatile Biologically Active Heterocyclic Scaffold

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