A review on recent progress in synthesis and biological activities of spiropyrrolidine and its derivatives

Journal of Molecular Structure, Год журнала: 2025, Номер unknown, С. 141377 - 141377

Опубликована: Янв. 1, 2025

Язык: Английский

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Design and Application of Chiral Bifunctional 4-Pyrrolidinopyridines: Powerful Catalysts for Asymmetric Cycloaddition of Allylic N-Ylide

ACS Catalysis, Год журнала: 2022, Номер 12(12), С. 7221 - 7232

Опубликована: Июнь 2, 2022

We designed bifunctional 4-pyrrolidinopyridines as powerful Lewis base catalysts. The catalyst structure features a 4-hydroxy-2-(hydroxydiphenylmethyl)pyrrolidine-1-formyl group at the pyridine's C3 site and chiral side arm C2 position of p-pyrrolidine ring. An operationally simple three-step synthetic route allows for efficient economical preparation. In comparison with other bases, exhibits excellent efficiency stereoselectivity in asymmetric (3 + 2) cycloaddition allylic N-ylide generated situ from pyrazolone-derived Morita–Baylis–Hillman carbonate, providing platform construction spiropyrazolone derivatives. reaction mechanism was thoroughly studied. Control experiments DFT calculations illustrated origin chemoselectivity stereocontrol model. H-bonding is crucial control enantioselectivity diastereoselectivity. also successfully applied reactions, such an acylative dynamic kinetic resolution to synthesize phthalidyl ester, including prodrug Talmetacin.

Язык: Английский

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Synthesis of Spiro[indoline-pyridine]-dicarboxylates and Substituted Alkylidene Oxindoles by Azomethine Ylides and MBH Carbonates of Isatins

Organic Letters, Год журнала: 2024, Номер 26(19), С. 4117 - 4121

Опубликована: Май 9, 2024

We have developed an efficient protocol for the synthesis of spiro[indoline-pyridine]dicarboxylates and substituted alkylidene oxindoles through [3 + 3] cycloaddition Michael addition individually by azomethine ylides various MBH carbonates isatins. The selective generation cyclic products chain was achieved changing substituents at 3-position oxindoles. features this method include convenient catalysts, mild reaction conditions, broad substrate scopes.

Язык: Английский

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Convenient Synthetic Protocols for Diverse Functionalized Dihydrobenzofuran-Fused Spiro-indanedione-oxindole Scaffolds

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(16), С. 11562 - 11580

Опубликована: Июль 27, 2023

Diverse functionalized dihydrobenzofuran spiro-indanedione-oxindole scaffolds were conveniently synthesized by base-promoted cyclization reaction of Morita-Baylis-Hillman (MBH) carbonates isatins and 2-(o-hydroxybenzylidene)-1,3-indanediones. The two diastereomeric dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines] could be selectively using DABCO or DMAP as a base promoter. More importantly, facilitated the annulation MBH formates 2-(o-hydroxybenzylidene)-1,3-indanediones selectively, resulting in spiro[cyclopropa[c]chromene-1,2'-indene]-1',3'-diones dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines]. Additionally, similar with maleimides afforded dispiro[indene-2,5'-benzofuro[2',3':1,5]cyclopenta[1,2-c]pyrrole-4',3″'-indolines] high yields diastereoselectivity.

Язык: Английский

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An Access to Highly Functionalized Dihydrobenzofuran Spirooxindole Scaffolds

Organic Letters, Год журнала: 2022, Номер 24(42), С. 7790 - 7795

Опубликована: Окт. 14, 2022

We have developed an efficient protocol for the construction of polycyclic dihydrobenzofuran spirooxindole scaffolds via base promoted cascade annulation Morita-Baylis-Hillman (MBH) carbonates isatins with ortho-hydroxychalcones or ortho-hydroxy-β-nitrostyrenes. The complex compounds were conveniently synthesized in satisfactory yields and high diastereoselectivity. This provides a swift convenient approach assembly diverse highly functionalized spirooxindoles also features broad substrate scope, molecular convergence, excellent atomic economy.

Язык: Английский

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Selective construction of spiro[indoline-3,5′-pyrrolo[3,4-b]azepines] and spiro[indoline-3,3′-pyrroles] via a [4 + 3]/[3 + 2] cycloaddition reaction of α,β-unsaturated aldimines and MBH adducts of isatins

Organic Chemistry Frontiers, Год журнала: 2022, Номер 10(2), С. 540 - 547

Опубликована: Дек. 10, 2022

An efficient synthetic protocol for the selective construction of spiro[indoline-3,5′-pyrrolo[3,4- b ]azepines] and spiro[indoline-3,3′-pyrroles] via a cycloaddition reaction α,β-unsaturated aldimines MBH adducts isatins was successfully developed.

Язык: Английский

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Synthesis, Characterization, and Cytotoxicity of New Spirooxindoles Engrafted Furan Structural Motif as a Potential Anticancer Agent

ACS Omega, Год журнала: 2022, Номер 7(40), С. 35743 - 35754

Опубликована: Сен. 27, 2022

A new series of spirooxindoles based on ethylene derivatives having furan aryl moiety are reported. The hybrids were achieved via [3 + 2] cycloaddition reaction as an economic one-step efficient approach. final constructed have four contiguous asymmetric carbon centers. structure 3a is exclusively confirmed using X-ray single crystal diffraction. supramolecular controlled by O···H, H···H, and C···C intermolecular contacts. It includes layered molecules interconnected weak C-H···O (2.675 Å), H···H (2.269 relatively short Cl···Br interhalogen interactions [3.4500(11)Å]. Using Hirshfeld analysis, the percentages these contacts 10.6, 25.7, 6.4, 6.2%, respectively. along with assessed against breast (MCF7) liver (HepG2) cancer cell lines. results indicated that chalcone 3b showed excellent activity in both lines (MCF7 HepG2) IC50 = 4.1 ± 0.10 μM/mL 3.5 0.07 compared to staurosporine 4.3 2.92 folds. Spirooxindoles 6d (IC50 0.18 μM/mL), 6f 10.3 0.40 6i 10.7 0.38 6j 4.7 μM/mL) exhibited potential adenocarcinoma, while compounds 6.9 0.23 0.11 most active human line [IC50 17.8 0.50 (HepG2)]. Molecular docking study virtual mechanism binding compound a dual inhibitor EGFR/CDK-2 proteins, this may highlight molecular targets for its cytotoxic activity.

Язык: Английский

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Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita–Baylis–Hillman Carbonates with 3-Methyleneoxindoles

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(5), С. 3184 - 3194

Опубликована: Фев. 8, 2022

A type of Morita-Baylis-Hillman (MBH) carbonates has been developed from ninhydrin. These MBH have successfully employed as 3C-synthons in the organocatalytic asymmetric [3 + 2]-annulations isatin-derived electron-deficient olefins, affording structurally diverse spirooxindoles high yield with excellent stereoselectivity. In particular, regioselectivity was controlled by reaction partner, 3-methyleneoxindoles carbonyl groups (R = ArCO), β-selective products and ester CO2Me) furnishing γ-selective products. The representative scale-up reactions transformation product were examined. mechanism expounded control experiments.

Язык: Английский

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Efficient construction of diverse spiro[indoline-3,4′-pyrrolo[3,4-b]pyridines] via [3 + 3] cycloaddition of MBH carbonates of isatins with β-enamino maleimides

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(35), С. 7099 - 7104

Опубликована: Янв. 1, 2022

An efficient method to construct unique spiro[indoline-3,4′-pyrrolo[3,4- b ]pyridines] was successfully developed via a DABCO promoted formal [3 + 3] cycloaddition reaction of MBH carbonates isatins with β-enamino maleimides under mild conditions.

Язык: Английский

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Base-Mediated Annulation of ortho-Iminophenols and ortho-Vinylphenols with MBH Carbonates of Isatins: Straightforward Access to Dihydrobenzofuran and Benzofuran Derivatives

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(21), С. 15472 - 15489

Опубликована: Окт. 15, 2024

We have developed a convenient synthetic protocol for efficient construction of significant dihydrobenzofuran and benzofuran scaffolds by Lewis base-mediated annulation reaction ortho-iminophenols ortho-vinylphenols with MBH carbonates isatins under mild metal-free conditions. The selective generation different kinds derivatives was successfully achieved employing substituted isatin-derived ortho-N-tosyliminophenols ortho-vinylphenols. features included broad substrate scopes, excellent functional group compatibility, high molecular diversity, atomic economy.

Язык: Английский

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