Spirocyclic compounds: potential drug leads in the fight against Mycobacterium tuberculosis

Future Medicinal Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 19

Published: March 19, 2025

TB drug discovery needs scientists' attention since resistance in TB, including extensively drug-resistant (XDR-TB) and multidrug-resistant (MDR-TB), is a major healthcare concern. Since millions of fatalities from tuberculosis are recorded each year, there an urgent need to discover new anti-tubercular medications that will either eradicate or control the disease. Spiro compounds have garnered lot medicinal chemistry these days because various biological activities mainly their adaptability structural resemblance significant pharmacophores. This article overviews synthesis activity spirocyclic as agents. Both synthesized naturally occurring spiro chemicals exhibit antitubercular properties. The promising potential shown by some has attracted scientists explore them further develop molecules with improved pharmacodynamic pharmacokinetic properties mechanisms action enhanced safety efficacy tuberculosis. current review covers exploration year 2004 2024 for combat Tuberculosis. gives comprehensive advancements this scaffold which would help logical design powerful, less toxic, more effective anti-TB molecules.

Language: Английский

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Spirooxindoles: Recent report of green synthesis approach

Green Synthesis and Catalysis, Journal Year: 2023, Volume and Issue: 5(1), P. 1 - 13

Published: Aug. 15, 2023

Spirooxindole is a compound with unique framework and broad bioactivities in medicine. In this study, we have reviewed various approaches or methods synthesizing spirooxindole derivatives focused on green synthesis. Synthesis of spirooxindoles mainly carried out through multicomponent reactions combined such as the use heterogeneous catalysts (nano-sized, magnetic, metal-complex, metal-organic catalysts), deep eutectic solvent, solvent-free reactions, catalyst-free well ultrasonic microwaves irradiation. The method addition to obtaining high yields, it also offers reductions hazardous chemicals, energy use, purification processes, waste generation. As result, synthesis are more environmentally friendly.

Language: Английский

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An Access to Highly Functionalized Dihydrobenzofuran Spirooxindole Scaffolds

Organic Letters, Journal Year: 2022, Volume and Issue: 24(42), P. 7790 - 7795

Published: Oct. 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.

Language: Английский

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Synthesis spiro and fused chromenes via [4 + 2] cycloaddition of salicyl N-tosylimines and cyclic dienophiles

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1304, P. 137684 - 137684

Published: Feb. 4, 2024

Language: 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, Journal Year: 2022, Volume and Issue: 20(35), P. 7099 - 7104

Published: Jan. 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.

Language: Английский

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Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10854 - 10866

Published: July 12, 2024

A convenient synthetic protocol for diverse fused chromenes was successfully developed by a three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and various cyclic 1,3-dipolarophiles containing

Language: Английский

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Lewis Acid-Catalyzed [3 + 2]-Cyclization of Iodonium Ylides with Azadienes: Access to Spiro[benzofuran-2,2′-furan]-3-ones

Organic Letters, Journal Year: 2022, Volume and Issue: 24(41), P. 7502 - 7506

Published: Oct. 11, 2022

A highly regioselective synthesis of spiro[benzofuran-2,2'-furan]-3-ones has been explored via Lewis acid-catalyzed [3 + 2] cyclization iodonium ylides with azadienes. The acidity the acid was significantly strengthened strong hydrogen bond donors, thereby promoting enolization isomerization for subsequent cycloaddition. This reaction compatible a broad range substrates under mild conditions, and efficiently delivered spiro-heterocycles excellent stereoselectivity.

Language: Английский

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Synthesis of Oxo-Bridged Dibenzoazocines through Ruthenium-Catalyzed [4 + 3]-Cycloannulation of Aza-ortho-quinone Methides with Carbonyl Ylides

Organic Letters, Journal Year: 2023, Volume and Issue: 25(27), P. 5134 - 5139

Published: June 30, 2023

Oxo-bridged dibenzoazocines are furnished within a single synthetic step at room temperature via ruthenium-catalyzed [4 + 3]-cycloannulation of aza-ortho-quinone methides with carbonyl ylides. Exclusive diastereoselectivity, excellent yield, mild reaction conditions, and broad substrate scope distinguishing features this protocol. The product could be prepared on gram scale further functionalized into diverse substituted dihydroisobenzofuran derivatives dibenzoazocine scaffold.

Language: Английский

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Construction of Spiro[indoline‐3,2′‐pyrrolo[2,1‐a]Isoquinoline] and Spiro[indoline‐3,2′‐pyrrolo[1,2‐a]Quinoline] via Isocyanide‐Based Three‐Component Reaction

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(4)

Published: Jan. 1, 2025

Abstract A convenient synthetic protocol for novel spiro[indoline‐3,2′‐pyrrolo[2,1‐ a ]isoquinoline] and spiro[indoline‐3,2′‐pyrrolo[1,2‐ ]quinoline] motifs was successfully developed by three‐component reaction of isoquinoline (quinoline), cyclohexyl isocyanide, isatylidene malononitriles. In the absence any catalyst, isoquinoline, malononitriles in refluxing dichloromethane gave functionalized ]isoquinolines] good yields with high diastereoselectivity. However, similar quinoline afforded ]quinolines] about 2:1

Language: Английский

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Rh-Catalyzed [3+2] Annulation of Cyclic Ketimines and Alkynyl Chloride: A Strategy for Accessing Unsymmetrically Substituted and Highly Functionalizable Indenes

Organic Letters, Journal Year: 2022, Volume and Issue: 24(50), P. 9169 - 9173

Published: Dec. 12, 2022

Alkynyl chlorides were found to be extraordinarily novel electrophiles, which could afford a single regioisomer of the [3+2] annulation adducts with cyclic ketimines by rhodium catalysis. The alkenyl chloride moiety in products provided valuable functional handle for further diverse transformations. Therefore, this research not only synthetic protocol accessing unsymmetrically substituted indenyl amines but also highly divergent solution decorating substituting group postmanipulation chloride.

Language: Английский

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