Synthesis of Naphthoquinone‐ and Pyrrolo[2,1‐<i>a</i>]isoquinoline‐Fused Heterocycles and Tridemethoxy Lamellarin D

Jhang, Jia-Wei; Manjappa, Kiran B.; Yang, Ding‐Yah

doi:10.1002/ajoc.202100660

Cited by 7 publications

(3 citation statements)

References 36 publications

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“…Jhang et al reported a facile synthesis of pyrrolo[2,1- a ]isoquinoline tethered naphthoquinone 359 (Scheme 72). 117 Direct oxidative coupling of naphthalene-1,4-dione 356 with papaverine 357 in the presence of Lewis acid catalyst ZnCl 2 furnishes tetra- and hexamethoxy isoquinoline derivatives 358 . Demethylation of 358 with excess BBr 3 affords the pentacyclic isoquinoline scaffolds 359a–b .…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Diversely functionalized isoquinolines and their core-embedded heterocyclic frameworks: a privileged scaffold for medicinal chemistry

Vijayakumar,

Manod,

Krishna

et al. 2023

RSC Med. Chem.

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Section: Miscellaneous Reactionsmentioning

confidence: 99%

Diversely functionalized isoquinolines and their core-embedded heterocyclic frameworks: a privileged scaffold for medicinal chemistry

Vijayakumar,

Manod,

Krishna

et al. 2023

RSC Med. Chem.

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“…Mpro in (Figure 4A) by the benzyl and -lactam moieties. Contrary to what has been reported for anti-HIV activity [105], the presence of sulfate groups does not appear to Moreover, considering the valid and easily accessible chemical syntheses for a numerous number of these marine compounds and their structurally related congeners, which could be encouraging for more in vitro /in vivo preclinical investigations [60,[106][107][108][109].…”

Section: Figure 14 Polycyclic Core Of the Lamellarin-derived Pyrrole ...mentioning

confidence: 99%

Investigating the Antiviral Therapeutic Potentialities of Marine Polycyclic Lamellarin Pyrrole Alkaloids as Promising Inhibitors for SARS-CoV-2 and Zika Main Proteases (Mpro)

Pereira

Bedda

Tammam

et al. 2022

Preprint

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The new coronavirus variant (SARS-CoV-2) and Zika virus are two worldwide health pandemics which outbreak borders and causing significant health difficulties, severe economic problems, and disturbing people’s daily life globally. Although many forms of preventative vaccines have been discovered and approved as protective manipulations alongside several orally available medications to stop the viral explosion, parallel competent antivirals are vitally needed to compete these viruses and their forms. Along history, naturally occurring organic chemicals have always crucially recognized as a main source of valuable medications. Taking into consideration the SARS-CoV-2 and Zika main proteases (Mpro) as the re-production key element of the viral cycle and its main target, herein we report an intensive computer-aided virtual screening for a focused list of 39 marine lamellarins pyrrole alkaloids, against SARS-CoV-2 and Zika main proteases (Mpro) using a set of combined modern computational methodologies including molecular docking (MDock), molecule dynamic simulations (MDS) and structure-activity relationships (SARs) as well. Indeed, the molecular docking studies had revealed four promising marine alkaloids including [lamellarin H (14)/lamellarin K (17)] and [lamellarin S (26)/ lamellarin Z (39)], according to their notable ligand-protein energy scores and relevant binding affinities with the SARS-CoV-2 and Zika (Mpro) pocket residues, respectively. Consequentially, these four chemical hits were further examined thermodynamically though investigating their MD simulations at 100 ns, where they showed prominent stability within the accommodated (Mpro) pockets. Moreover, in-deep SARs studies suggested the crucial roles of the rigid fused polycyclic ring system, particularly aromatic A- and F- rings, position of the phenolic -OH and -lactone functionalities as essential structural and pharmacophoric characteristics for an effective protein ligand interaction against SARS-CoV-2 and Zika Mpro, respectively. These motivating outcomes are greatly recommending further in vitro/vivo examinations regarding those marine derived compounds and their synthetic congeners, opening the gate to identify clinically useful antivirals based or bio-inspired from lamellarins pyrrole alkaloids (LPAs).

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“…In 2022, Yang et al 59 extended the application of the Grob-coupling reaction for the synthesis of tridemethoxy lamellarin D. This compound was synthesized via base-mediated Grob coupling of 1-methylisoquinoline and 7-methoxy-3-nitrocoumarin as the key step in the presence of NaHCO 3 in dichloroethane (DCE) as a solvent in a sealed tube at 105 °C. Bromination of the pyrrole ring with NBS followed by palladium-catalyzed Suzuki–Miyaura coupling reaction with arylboronic acid afforded the desired product tridemethoxy lamellarin D in good yield in both steps (Scheme 4).…”

Section: Introductionmentioning

confidence: 99%

Recent advances in the synthesis of chromenone fused pyrrolo[2,1-a]isoquinoline derivatives

Bera,

Maji,

Patra

et al. 2023

New J. Chem.

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Synthesis of Naphthoquinone‐ and Pyrrolo[2,1‐a]isoquinoline‐Fused Heterocycles and Tridemethoxy Lamellarin D

Cited by 7 publications

References 36 publications

Diversely functionalized isoquinolines and their core-embedded heterocyclic frameworks: a privileged scaffold for medicinal chemistry

Diversely functionalized isoquinolines and their core-embedded heterocyclic frameworks: a privileged scaffold for medicinal chemistry

Investigating the Antiviral Therapeutic Potentialities of Marine Polycyclic Lamellarin Pyrrole Alkaloids as Promising Inhibitors for SARS-CoV-2 and Zika Main Proteases (Mpro)

Recent advances in the synthesis of chromenone fused pyrrolo[2,1-a]isoquinoline derivatives

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