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Coumarin—Synthetic Methodologies, Pharmacology, and Application as Natural Fluorophore

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Topics in Current Chemistry
Authors:
Deepshikha Gupta at Amity University
Deepshikha Gupta
Eksha Guliani at Manav Rachna University
Eksha Guliani
  • Manav Rachna University
Kiran Bajaj at Amity University
Kiran Bajaj
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Abstract and Figures

Coumarins are secondary metabolites made up of benzene and α-pyrone rings fused together that can potentially treat various ailments, including cancer, metabolic, and degenerative disorders. Coumarins are a diverse category of both naturally occurring as well as synthesized compounds with numerous biological and therapeutic properties. Coumarins as fluorophores play a key role in fluorescent labeling of biomolecules, metal ion detection, microenvironment polarity detection, and pH detection. This review provides a detailed insight into the characteristics of coumarins as well as their biosynthesis in plants and metabolic pathways. Various synthetic strategies for coumarin core involving both conventional and green methods have been discussed comparing advantages and disadvantages of each method. Conventional methods discussed are Pechmann, Knoevenagel, Perkin, Wittig, Kostanecki, Buchwald-Hartwig, and metal-induced coupling reactions such as Heck and Suzuki, as well as green approaches involving microwave or ultrasound energy. Various pharmacological applications of coumarin derivatives are discussed in detail. The structural features and conditions responsible for influencing the fluorescence of coumarin core are also elaborated. Graphical Abstract
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Vol.:(0123456789)
Topics in Current Chemistry (2024) 382:16
https://doi.org/10.1007/s41061-024-00462-z
1 3
REVIEW
Coumarin—Synthetic Methodologies, Pharmacology,
andApplication asNatural Fluorophore
DeepshikhaGupta1· EkshaGuliani1· KiranBajaj1
Received: 22 November 2023 / Accepted: 9 April 2024 / Published online: 9 May 2024
© The Author(s), under exclusive licence to Springer Nature Switzerland AG 2024
Abstract
Coumarins are secondary metabolites made up of benzene and α-pyrone rings fused
together that can potentially treat various ailments, including cancer, metabolic,
and degenerative disorders. Coumarins are a diverse category of both naturally
occurring as well as synthesized compounds with numerous biological and
therapeutic properties. Coumarins as fluorophores play a key role in fluorescent
labeling of biomolecules, metal ion detection, microenvironment polarity detection,
and pH detection. This review provides a detailed insight into the characteristics of
coumarins as well as their biosynthesis in plants and metabolic pathways. Various
synthetic strategies for coumarin core involving both conventional and green
methods have been discussed comparing advantages and disadvantages of each
method. Conventional methods discussed are Pechmann, Knoevenagel, Perkin,
Wittig, Kostanecki, Buchwald-Hartwig, and metal-induced coupling reactions such
as Heck and Suzuki, as well as green approaches involving microwave or ultrasound
energy. Various pharmacological applications of coumarin derivatives are discussed
in detail. The structural features and conditions responsible for influencing the
fluorescence of coumarin core are also elaborated.
* Deepshikha Gupta
dgupta2@amity.edu
1 Amity Institute ofApplied Sciences, Amity University Uttar Pradesh, Sector 125, Noida, India
Content courtesy of Springer Nature, terms of use apply. Rights reserved.
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... Coumarins, a class of naturally occurring heterocyclic compounds, are frequently utilized in the synthesis of various biologically and pharmacologically active substances [38][39][40]. In V. yedoensis, coumarin compounds represent a significant class of constituents, with maining coumarin compounds are categorized as simple coumarins. ...
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Pechmann Reaction in the Synthesis of Coumarin Derivatives
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