Cuspareine as alkaloid against COVID-19 designed with ionic liquids: DFT and docking molecular approaches

Mahani, Nosrat Madadi; Mostaghni, Fatemeh; Shafiekhani, Homa

doi:10.1016/j.jphotobiol.2022.112447

Cited by 7 publications

(1 citation statement)

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“…It is noteworthy that 2‐methylbenzothiazole and 2‐methylquinoxaline were also tolerated under these coupling conditions to from the products in acceptable yields ( 3 ga , 3 ha , and 3 hf ). Gratifyingly, two pharmaceutically significant taconjugated olefins 3 ah and 3 ea , which is the precursor of antimalarial drug (±)‐Cuspareine [24] and the core structure of the drug Montelukast [25] respectively, were obtained in high yields. Furthermore, the gram‐scale synthesis of 3 aa was also successful, giving a 82 % yield from 1 a (1 g scale) after increasing the reaction time to 48 h ( 3 aa [b] ).…”

Section: Resultsmentioning

confidence: 99%

4,6‐Dihydroxysalicylic Acid‐Catalyzed Oxidative Olefination of Methyl N‐Heteroarenes with Benzyl Amines

et al. 2023

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Benzyl amines were deaminated for the olefination of methyl N‐heteroarenes such as quinolines, benzothiazoles, and quinoxalines catalyzed by 4,6‐dihydroxysalicylic acid with only 1 mol % catalyst loading. A wide range of N‐heteroaryl stilbenoids were synthesized in yields of 42 to 96 % using oxygen (1 atm) as the sole oxidant. 4,6‐dihydroxysalicylic acid not only behaves as an organocatalyst for the oxidation of benzyl amines to the imine intermediates, but also provides an acidic reaction condition for the olefinations. Gram scale reaction and the synthesis of two pharmaceutically relevant conjugated olefins were also successful using this methodology.

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Section: Resultsmentioning

confidence: 99%

4,6‐Dihydroxysalicylic Acid‐Catalyzed Oxidative Olefination of Methyl N‐Heteroarenes with Benzyl Amines

et al. 2023

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Nitrobenzene and Aniline‐Mediated Direct Olefination of Methyl Substituted N‐Heteroarenes With Benzylic Alcohols

Dong,

Mei,

et al. 2024

ChemistrySelect

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Metal‐free, strong‐base‐free, and solvent‐free synthesis of alkenyl heteroarenes through PhNO2/PhNH2 mediated direct olefination of methyl substituted N‐heteroarenes with benzylic alcohols was described. Detailed mechanistic studies indicated that in situ formed imine was the active intermediate for the olefination. PhNO2 protected benzylic alcohols from overoxidation, and PhNH2 not only acted as the coupling partner for the formation of intermediate imine, but also provides an alkaline condition for the generation of enamine salt. Gram scale reaction and the synthesis of three pharmaceutically relevant conjugated olefins were also successful using this methodology.

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Investigation on growth, Hirshfeld surface, optical, thermal and topological properties of nonlinear optical p-nitrophenol single crystal

Jyoti,

Vijayan,

Kiran

et al. 2024

J Mater Sci: Mater Electron

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Cuspareine as alkaloid against COVID-19 designed with ionic liquids: DFT and docking molecular approaches

Cited by 7 publications

References 50 publications

4,6‐Dihydroxysalicylic Acid‐Catalyzed Oxidative Olefination of Methyl N‐Heteroarenes with Benzyl Amines

4,6‐Dihydroxysalicylic Acid‐Catalyzed Oxidative Olefination of Methyl N‐Heteroarenes with Benzyl Amines

Nitrobenzene and Aniline‐Mediated Direct Olefination of Methyl Substituted N‐Heteroarenes With Benzylic Alcohols

Investigation on growth, Hirshfeld surface, optical, thermal and topological properties of nonlinear optical p-nitrophenol single crystal

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