Spirooxindole: A Versatile Biologically Active Heterocyclic Scaffold

Molecules, Journal Year: 2023, Volume and Issue: 28(2), P. 618 - 618

Published: Jan. 7, 2023

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

Language: Английский

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Sustainable one-pot synthesis of novel soluble cellulose-based nonionic biopolymers for natural antimicrobial materials

Chemical Engineering Journal, Journal Year: 2023, Volume and Issue: 468, P. 143810 - 143810

Published: May 31, 2023

Language: Английский

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Expeditious entry into carbocyclic and heterocyclic spirooxindoles

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(29), P. 5651 - 5693

Published: Jan. 1, 2022

Recent advances in the chemistry of base-, metal-, nano-metal and organo-catalyst mediated achiral chiral versions structurally diverse pharmaceutically relevant spirooxindoles are gently reviewed.

Language: Английский

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Synergistic applications of nanocomposite, ultrasound, and on‐water synthesis for efficient and green synthesis of spirooxindole derivatives via cascade C–N, C–O, and C–S bond formation

Applied Organometallic Chemistry, Journal Year: 2024, Volume and Issue: 38(4)

Published: Feb. 7, 2024

A highly efficient, green, and multicomponent reaction method has been developed for the diversity‐oriented synthesis of 32 spirooxindole derivatives via formation cascade C–N, C–O, C–S bonds. The involved starch‐capped zinc oxide nanocomposite as an effective heterogeneous catalyst with synergistic application ultrasound on‐water synthesis. By employing this approach, all desired products were successfully obtained high yields comparatively short times. Furthermore, employed in process exhibited excellent recyclability, allowing its recovery reuse up to eight consecutive runs without any loss catalytic activity. greenness protocol was evaluated by various green metrics such E‐factor eco‐score, result showed acceptability present organic

Language: Английский

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Relay Annulation of Ammonium Ylides with Oxindole-Derived α,β-Unsaturated Ketimines: Catalytic Construction of Spiro-polycyclic Oxindoles

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5115 - 5119

Published: June 11, 2024

An ammonium ylide-based relay annulation was disclosed, which uses DABCO as the catalyst and oxindole-derived α,β-unsaturated ketimines γ-bromo-crotonates starting materials. This method enables rapid assembly of a series structurally novel spiro-polycyclic oxindoles containing bicyclo[4.1.0]heptane moiety through simultaneous generation three new bonds two rings in one step under mild reaction conditions.

Language: Английский

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Eco-Friendly Cellulose-Based Nonionic Antimicrobial Polymers with Excellent Biocompatibility, Nonleachability, and Polymer Miscibility

ACS Applied Materials & Interfaces, Journal Year: 2023, Volume and Issue: 15(43), P. 50344 - 50359

Published: Oct. 20, 2023

This study aims to prepare natural biomass-based nonionic antimicrobial polymers with excellent biocompatibility, nonleachability, activity, and polymer miscibility. Two new cellulose-based (MIPA MICA) containing many terminal indole groups were synthesized using a sustainable one-pot method. The structures properties of the characterized nuclear magnetic resonance hydrogen spectroscopy (1H NMR), infrared (FTIR), wide-angle X-ray diffractometry (XRD), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), electron microscopy (SEM), gel chromatography (GPC), other analytical techniques. results showed that microcrystalline cellulose (MCC) molecules combined derivatives through an esterification reaction produce MICA MIPA. crystallinity prepared MIPA decreased after MCC modification; their morphological structure changed from short fibrous granular better thermal stability solubility. paper diffusion method both had good bactericidal effects against two common pathogenic bacteria Escherichia coli (E. coli, inhibition zone diameters >22 mm) Staphylococcus aureus (S. aureus, >38 mm). Moreover, miscibility biodegradable poly(vinyl alcohol) (PVA), miscible composite films (PVA-MICA PVA-MIPA) phase compatibility, light transmission, (maximum decomposition temperature >300 °C), biological cell activity (no cytotoxicity), mechanical fracture elongation at >390%).

Language: Английский

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Discovery of a cytochrome P450 enzyme catalyzing the formation of spirooxindole alkaloid scaffold

Frontiers in Plant Science, Journal Year: 2023, Volume and Issue: 14

Published: Feb. 3, 2023

Spirooxindole alkaloids feature a unique scaffold of an oxindole ring sharing atom with heterocyclic moiety. These compounds display extensive range biological activities such as anticancer, antibiotics, and anti-hypertension. Despite their structural functional significance, the establishment rationale spirooxindole biosynthesis are yet to be elucidated. Herein, we report discovery characterization cytochrome P450 enzyme from kratom (Mitragyna speciosa) responsible for formation 3-epi-corynoxeine (3R, 7R) isocorynoxeine (3S, 7S) corynanthe-type (3R)-secoyohimbane precursors. Expression newly discovered in Saccharomyces cerevisiae yeast allows efficient vivo vitro production spirooxindoles. This highlights versatility plant enzymes building unusual alkaloid scaffolds opens gateway access prestigious pharmacophore its derivatives.

Language: 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, Journal Year: 2022, Volume and Issue: 87(5), P. 3184 - 3194

Published: Feb. 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.

Language: Английский

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Visible‐Light‐Mediated Direct Expeditious Photochemical Construction of Spirocyclic‐Oxindoles

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(3)

Published: Feb. 3, 2023

Abstract Spirocyclic compounds, particularly spirooxindoles that comprise a tetrahedral sp 3 ‐hybridized carbon atom at the C‐3 position of an orthogonally shaped bicyclic structure have recently received increasing attention in drug discovery and development, besides their major potential natural products synthetic organic chemistry. They are found to be structural constituents many alkaloids, key active building blocks for construction various pharmaceutically significant molecules. On other hand, with awareness people about protecting health living environment from pollution caused by chemical laboratories industry, development method provides alternatives traditional one introducing economical sustainable processes is scientifically technically demanding but challenging. To address these concerns inspired photosynthesis process, visible light‐induced chemistry appears highly economic, sustainable, alternative approach synthesis. The present mini‐review aims highlight recent progress accomplished straightforward accelerated light irradiation period 2015 date. Besides reviewing advantages achieved this field, we also attempt find out drawback, mechanistic rationalization, scopes future applications.

Language: Английский

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Novel spiroindoline quinazolinedione derivatives as anticancer agents and potential FLT3 kinase inhibitors

Bioorganic & Medicinal Chemistry, Journal Year: 2023, Volume and Issue: 90, P. 117367 - 117367

Published: June 10, 2023

Language: Английский

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