A Brief Review on the Synthesis of Pyrrolo[2,3-<i>c</i>]coumarins, including Lamellarin and Ningalin Scaffolds

Patra, Prasanta; Manna, Sibasish; Patra, Susanta; Samanta, Khokan; Roy, D. B.

doi:10.1080/00304948.2022.2116909

Cited by 6 publications

(3 citation statements)

References 74 publications

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“…Further investigations are neces-sary to unveil the physiological and pharmacological potential of these compounds. [51][52][53][54] There are two primary synthetic methods for producing pyrrolo[g]coumarins: the construction of the pyranone-ring and the benzopyrrole-ring approaches. [55][56][57]…”

Section: Pyrrolo[g]coumarinsmentioning

confidence: 99%

“…While merging the pyrrole ring with coumarin to create the nitrogen analogue in furo[g]coumarin is a viable approach, it hasn′t been extensively explored in medicinal chemistry studies. Further investigations are necessary to unveil the physiological and pharmacological potential of these compounds [51–54] . There are two primary synthetic methods for producing pyrrolo[g]coumarins: the construction of the pyranone‐ring and the benzopyrrole‐ring approaches [55–57] …”

Section: Ahccs Containing a Single Heteroatom Within A Five‐membered ...mentioning

confidence: 99%

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Annulated Heterocyclic[g]Coumarin Composites: Synthetic Approaches and Bioactive Profiling

Mazin Zeki,

Fakri Mustafa

2024

Chemistry & Biodiversity

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Coumarins, widely abundant natural heterocyclic compounds, are extensively employed in creating various biologically and pharmacologically potent substances. The hybridization of heterocycles presents a key opportunity to craft innovative multicyclic compounds with enhanced biological activity. Fusing different heterocyclic rings with the coumarin structure presents an intriguing method for crafting fresh hybrid compounds possessing remarkable biological effects. In the pursuit of creating heterocyclic‐fused coumarins, a wide range of annulated heterocyclic[g]coumarin composites has been introduced, displaying impressive biological potency. The influence of the linear attachment of heterocyclic rings to the coumarin structure on the biological performance of the resulting compounds has been investigated. This review centers on the synthetic methodologies, structural activity relationship investigation, and biological potentials of annulated heterocyclic[g]coumarin composites. We conducted searches across several databases, including Web of Science, Google Scholar, PubMed, and Scopus. After sieving, we ultimately identified and included 71 pertinent studies published between 2000 and the middle of 2023. This will provide valuable perspectives for medicinal chemists in the prospective design and synthesis of lead compounds with significant therapeutic effects, centered around heterocycle‐fused coumarin frameworks.

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Section: Pyrrolo[g]coumarinsmentioning

confidence: 99%

Section: Ahccs Containing a Single Heteroatom Within A Five‐membered ...mentioning

confidence: 99%

Annulated Heterocyclic[g]Coumarin Composites: Synthetic Approaches and Bioactive Profiling

Mazin Zeki,

Fakri Mustafa

2024

Chemistry & Biodiversity

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“…Here, we review the recent literature on synthesizing distinctly oriented 2H/4Hchromen-2/4-one fused to the five-membered ring of pyrrolo-[2,1-a]isoquinolines and their derivatives from suitable precursors covering the advances from 2016 to 2023. Although some of the methods have been discussed in related surveys, 20,[52][53][54][55] to the best of knowledge, this is the first review specifically covering both 2H/4H-chromen-2/4-one fused to the fivemembered ring of pyrrolo[2,1-a]isoquinolines. We have classified our review into several sections based on the starting materials, strategies and use of catalysts, and according to various modes of ring construction.…”

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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Chromenone‐Fused Pyrrolizines and Pyrrolizine Analogues of Lamellarins: Expanding the Lamellarin Family

Scalzullo,

Morgans,

Klintworth

et al. 2024

Eur J Org Chem

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Several N‐ethoxycarbonylmethyl enaminones, prepared by Eschenmoser sulfide contraction between N‐(ethoxycarbonylmethyl)‐pyrrolidine‐2‐thione and various ortho‐oxygenated phenacyl halides, underwent cyclisation to give ethyl 6‐aryl‐2,3‐dihydro‐1H‐pyrrolizine‐5‐carboxylates upon microwave heating with silica gel in xylene. With enaminones made from ortho‐hydroxyphenacyl halides, not only did dihydropyrrolizine formation take place, but spontaneous lactonisation also occurred to give 9,10‐dihydrochromeno[4,3‐b]pyrrolizin‐6(8H)‐ones. Bromination and Suzuki–Miyaura arylation of these chromenopyrrolizines at the free C‐H site on the pyrrole ring afforded four analogues of the lamellarin alkaloids in which a pyrrolidine ring replaces the isoquinoline system in the fused polycyclic core. The product 11‐(3,4‐dimethoxyphenyl)‐2,3‐dimethoxy‐9,10‐dihydrochromeno[4,3‐b]pyrrolizin‐6(8H)‐one, in particular, is a congener of the well‐known lamellarin G trimethyl ether. Preliminary results pertaining to an extension to chromenone‐fused indolizines are also reported.

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A Brief Review on the Synthesis of Pyrrolo[2,3-c]coumarins, including Lamellarin and Ningalin Scaffolds

Cited by 6 publications

References 74 publications

Annulated Heterocyclic[g]Coumarin Composites: Synthetic Approaches and Bioactive Profiling

Annulated Heterocyclic[g]Coumarin Composites: Synthetic Approaches and Bioactive Profiling

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

Chromenone‐Fused Pyrrolizines and Pyrrolizine Analogues of Lamellarins: Expanding the Lamellarin Family

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