Pyrrolo[2,1-<i>a</i>]isoquinoline scaffolds for developing anti-cancer agents

García Maza, Leidy J.; Salgado, Arturo Mendoza; Kouznetsov, Vladimir V.; Meléndez, Carlos M.

doi:10.1039/d3ra07047f

Cited by 8 publications

(2 citation statements)

References 89 publications

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“…Thus, the main reason for the interest in pyrrolo[1,2- a ]quinoline and pyrrolo[2,1- a ]isoquinoline is driven by the high biological activity of both scaffolds with a remarkable tendency to exhibit anticancer activity . At the same time, another trend has emerged in the last year toward the formation of synthetic toolbox for their functionalization; in particular, chlorination, bromination, nitration, sulfenilation, oxidation, formylation, benzylation, allenylation, methylthio- and aminomethylation reactions have been unveiled .…”

Section: Introductionmentioning

confidence: 99%

Cascade Synthesis of Pyrrolo[1,2-a]quinolines and Pyrrolo[2,1-a]isoquinolines via Formal [3 + 2]-Cycloaddition of Push–Pull Nitro Heterocycles with Carbonyl-Stabilized Quinolinium/Isoquinolinium Ylides

Osipov,

Demidov,

Artemenko

et al. 2024

J. Org. Chem.

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Various substituted pyrrolo[1,2-a]quinolines and pyrrolo[2,1-a]isoquinolines were synthesized in good to high yields by the Et3N-mediated reaction of push–pull 3-nitrobenzofurans or 1-Ts-/1-Ms-3-nitroindoles and precursors of carbonyl-stabilized quinolinium and isoquinolinium ylides as 1,3-dipole equivalents. These transformations proceed in a one-pot manner starting with the formal [3 + 2]-cycloaddition stage, which is accompanied by double dearomatization of both quinoline/isoquinoline and benzofuran/indole moieties, followed by ring-opening of cyclic intermediate formed and nitrous acid elimination sequence. [3 + 2]-Cycloadducts were isolated as the final products in cases of impossibility or difficulty of their enolization. The present protocol was successfully extended to 3-nitro-4H-chromene derivatives as push–pull dipolarophile component. Finally, using the method of competing reactions, the reactivity of the starting compounds was compared with each other.

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Section: Introductionmentioning

confidence: 99%

Cascade Synthesis of Pyrrolo[1,2-a]quinolines and Pyrrolo[2,1-a]isoquinolines via Formal [3 + 2]-Cycloaddition of Push–Pull Nitro Heterocycles with Carbonyl-Stabilized Quinolinium/Isoquinolinium Ylides

Osipov,

Demidov,

Artemenko

et al. 2024

J. Org. Chem.

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“…2,3 In light of its importance in this regard, numerous studies have been devoted to the synthesis of pyrrolo[2,1- a ]isoquinoline. 4…”

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confidence: 99%

Photo-induced tungsten-catalyzed cascade synthesis of pyrrolo[2,1-a]isoquinoline-1,3-dicarboxylate and its reaction mechanism

Wen,

Jin,

Qiu

et al. 2024

Chem. Commun.

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A Comprehensive Review of Synthetic Approaches Toward Lamellarin D and its Analogous

Sivaganesan,

VL,

Sahoo

et al. 2024

ChemistrySelect

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Lamellarin D, a naturally occurring molecule, isolated from marine molluscs, it exhibits potent pharmacological activities, such as topoisomerase I inhibition, antiproliferation, antiviral, insecticidal, antimetastatic and anticancer effects, making it a promising candidate for drug development. This review explores the synthesis of Lamellarin D employing various methodologies. These synthetic approaches have enabled researchers to access Lamellarin D and its analogous efficiently, facilitating further investigation into their biological properties. Our study summarizes the major contributions of these efforts to the larger synthetic community, primarily focusing on general synthetic techniques toward the Lamellarin D and its counterpart since its isolation in 1997 to the present.

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Pyrrolo[2,1-a]isoquinoline scaffolds for developing anti-cancer agents

Abstract: Fused pyrrolo[2,1-a]isoquinolines have emerged as compelling molecules with remarkably potent cytotoxic activity and topoisomerase inhibitors.

Cited by 8 publications

References 89 publications

Cascade Synthesis of Pyrrolo[1,2-a]quinolines and Pyrrolo[2,1-a]isoquinolines via Formal [3 + 2]-Cycloaddition of Push–Pull Nitro Heterocycles with Carbonyl-Stabilized Quinolinium/Isoquinolinium Ylides

Cascade Synthesis of Pyrrolo[1,2-a]quinolines and Pyrrolo[2,1-a]isoquinolines via Formal [3 + 2]-Cycloaddition of Push–Pull Nitro Heterocycles with Carbonyl-Stabilized Quinolinium/Isoquinolinium Ylides

Photo-induced tungsten-catalyzed cascade synthesis of pyrrolo[2,1-a]isoquinoline-1,3-dicarboxylate and its reaction mechanism

A Comprehensive Review of Synthetic Approaches Toward Lamellarin D and its Analogous

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