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Coumarin and Its Derivatives III
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Coumarin and Its Derivatives III

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (15 December 2024) | Viewed by 9178

Special Issue Editor

Dr. Maria João Matos

E-Mail Website
Guest Editor
Department of Organic Chemistry, Faculty of Pharmacy, University of Santiago de Compostela, 15782 Santiago de Compostela, Spain
Interests: coumarins; natural product chemistry; organic chemistry; medicinal chemistry; chemical biology; computational chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Coumarin is a privileged scaffold in medicinal chemistry. Its derivatives are widely distributed in nature and can be found in a large number of naturally occurring and synthetic bioactive molecules. This scaffold is a unique and versatile oxygen-containing heterocyclic structure, presenting a large conjugated system with electron-rich and charge transport properties. These properties are responsible for the interaction of this scaffold with other molecules, such as biomolecules and ions. Therefore, a great number of coumarin derivatives have been designed, synthetized, and evaluated against different pharmacological targets. In addition, coumarin-based ion receptors, fluorescent probes, and biological stains are growing quickly and have extensive applications with which to monitor enzyme activity and complex biological events in a timely manner, as well as accurately monitor pharmacological and pharmacokinetic properties in living cells. The extraction, synthesis, and biological evaluation of coumarins have become extremely attractive and rapidly developing topics. Research articles, reviews, communications, and concept papers focused on the multidisciplinary profile of coumarins, highlighting natural sources, most recently synthetic pathways, along with the main biological applications and theoretical studies, are welcome for this Special Issue.

Dr. Maria João Matos
Guest Editor

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Keywords

  • coumarins
  • natural products
  • synthesis
  • bioactivity
  • fluorescent dyes
  • computational studies
  • analytical methods
  • medicinal chemistry
  • chemical biology
  • drug discovery

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Related Special Issues

Published Papers (5 papers)

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Research

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19 pages, 1716 KiB  
Article
Elucidating the Mechanism of Coumarin Homodimerization Using 3-Acetylcoumarin Derivatives
by Kristina B. Simeonova, Ana I. Koleva, Nevena I. Petkova-Yankova, Anna-Mariya R. Zlatanova, Vesela Lozanova, Rositca D. Nikolova and Petko St. Petkov
Molecules 2025, 30(3), 651; https://doi.org/10.3390/molecules30030651 - 1 Feb 2025
Viewed by 677
Abstract
The current study is a continuation of our previous investigations into the radical homodimeric reaction mechanism of 3-acetylcoumarin. In the current study, the effects of different substituents on the coumarin ring of 3-acetylcoumarin are investigated both experimentally and theoretically. Several 3-acetylcoumarin derivatives (substituted [...] Read more.
The current study is a continuation of our previous investigations into the radical homodimeric reaction mechanism of 3-acetylcoumarin. In the current study, the effects of different substituents on the coumarin ring of 3-acetylcoumarin are investigated both experimentally and theoretically. Several 3-acetylcoumarin derivatives (substituted at C-6, C-7, and C-8) were tested in the optimized reaction conditions under ultrasound irradiation, and biscoumarin species were isolated and characterized. The elucidation of the substituent’s effect was further investigated by means of DFT calculations (free-energy calculations, NBO analysis), both in the initial substituted coumarins and in the formed radicals. It was observed that the presence of substituents at the C-6 and C-8 positions in the coumarin moiety would not affect significantly the formation of a radical, while a group at position C-7 could either stabilize or destabilize the formed radical depending on the electronic properties of the substituent. Full article
(This article belongs to the Special Issue Coumarin and Its Derivatives III)
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9 pages, 3148 KiB  
Article
Novel Dihydrocoumarins Induced by Radiolysis as Potent Tyrosinase Inhibitors
by Gyeong Han Jeong, Manisha Yadav, Seung Sik Lee, Byung Yeoup Chung, Jae-Hyeon Cho, In-Chul Lee, Hyoung-Woo Bai and Tae Hoon Kim
Molecules 2024, 29(2), 341; https://doi.org/10.3390/molecules29020341 - 10 Jan 2024
Cited by 5 | Viewed by 1356
Abstract
A representative naturally occurring coumarin, 4-methylumbelliferone (5), was exposed to 50 kGy of gamma ray, resulting in four newly generated dihydrocoumarin products 1–4 induced by the gamma irradiation. The structures of these new products were elucidated by interpretation of [...] Read more.
A representative naturally occurring coumarin, 4-methylumbelliferone (5), was exposed to 50 kGy of gamma ray, resulting in four newly generated dihydrocoumarin products 1–4 induced by the gamma irradiation. The structures of these new products were elucidated by interpretation of spectroscopic data (NMR, MS, [α]D, and UV). The unusual bisdihydrocoumarin 4 exhibited improved tyrosinase inhibitory capacity toward mushroom tyrosinase with IC50 values of 19.8 ± 0.5 μM as compared to the original 4-methylumbelliferone (5). A kinetic analysis also exhibited that the potent metabolite 4 had non-competitive modes of action. Linkage of the hydroxymethyl group in the C-3 and C-4 positions on the lactone ring probably enhances the tyrosinase inhibitory effect of 4-methylumbelliferone (5). Thus, the novel coumarin analog 4 is an interesting new class of tyrosinase inhibitory candidates that requires further examination. Full article
(This article belongs to the Special Issue Coumarin and Its Derivatives III)
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Review

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21 pages, 5932 KiB  
Review
Coumarins: Quorum Sensing and Biofilm Formation Inhibition
by Eslam R. El-Sawy, Mohamed S. Abdel-Aziz, Heba Abdelmegeed and Gilbert Kirsch
Molecules 2024, 29(19), 4534; https://doi.org/10.3390/molecules29194534 - 24 Sep 2024
Cited by 5 | Viewed by 2415
Abstract
Quorum sensing (QS) is a bacterial cell-to-cell communication mechanism that plays an essential role in bacterial pathogenesis. QS governs bacterial behavior and controls biofilm formation, which in turn contributes to antibiotic resistance. Therefore, identifying and synthesizing novel compounds to overcome QS and inhibit [...] Read more.
Quorum sensing (QS) is a bacterial cell-to-cell communication mechanism that plays an essential role in bacterial pathogenesis. QS governs bacterial behavior and controls biofilm formation, which in turn contributes to antibiotic resistance. Therefore, identifying and synthesizing novel compounds to overcome QS and inhibit biofilm formation are essential. Coumarins are important plant-derived natural products with wide-ranging bioactivities and extensive applications, including antibacterial, antifungal, anticoagulant, antioxidant, anticancer, and anti-inflammatory properties. Additionally, coumarins are capable of QS rewiring and biofilm formation inhibition, leading to higher susceptibility to antimicrobial agents and less antibiotic resistance. Therefore, in this review, we aim to provide an overview of QS and biofilm formation. This review also discusses the role of natural and synthesized coumarins in controlling QS, inhibiting biofilm formation, and inducing synergy in antibiotic–coumarin combinations. Hence, this review emphasizes the potential of coumarin compounds to act as antibacterial agents and demonstrates their ability to alleviate antibiotic resistance. Full article
(This article belongs to the Special Issue Coumarin and Its Derivatives III)
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73 pages, 18532 KiB  
Review
An Overview on the Synthesis of Lamellarins and Related Compounds with Biological Interest
by Vasiliki-Panagiota M. Mitsiou, Anastasia-Maria N. Antonaki, Matina D. Douka and Konstantinos E. Litinas
Molecules 2024, 29(17), 4032; https://doi.org/10.3390/molecules29174032 - 26 Aug 2024
Cited by 4 | Viewed by 1533
Abstract
Lamellarins are natural products with a [3,4]-fused pyrrolocoumarin skeleton possessing interesting biological properties. More than 70 members have been isolated from diverse marine organisms, such as sponges, ascidians, mollusks, and tunicates. There is a continuous interest in the synthesis of these compounds. In [...] Read more.
Lamellarins are natural products with a [3,4]-fused pyrrolocoumarin skeleton possessing interesting biological properties. More than 70 members have been isolated from diverse marine organisms, such as sponges, ascidians, mollusks, and tunicates. There is a continuous interest in the synthesis of these compounds. In this review, the synthetic strategies for the synthesis of the title compounds are presented along with their biological properties. Three routes are followed for the synthesis of lamellarins. Initially, pyrrole derivatives are the starting or intermediate compounds, and then they are fused to isoquinoline or a coumarin moiety. Second, isoquinoline is the starting compound fused to an indole moiety. In the last route, coumarins are the starting compounds, which are fused to a pyrrole moiety and an isoquinoline scaffold. The synthesis of isolamellarins, azacoumestans, isoazacoumestans, and analogues is also described. The above synthesis is achieved via metal-catalyzed cross-coupling, [3 + 2] cycloaddition, substitution, and lactonization reactions. The title compounds exhibit cytotoxic, multidrug resistance (MDR), topoisomerase I-targeted antitumor, anti-HIV, antiproliferative, anti-neurodegenerative disease, and anti-inflammatory activities. Full article
(This article belongs to the Special Issue Coumarin and Its Derivatives III)
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24 pages, 4777 KiB  
Review
Naturally Inspired Coumarin Derivatives in Alzheimer’s Disease Drug Discovery: Latest Advances and Current Challenges
by Rebecca Orioli, Federica Belluti, Silvia Gobbi, Angela Rampa and Alessandra Bisi
Molecules 2024, 29(15), 3514; https://doi.org/10.3390/molecules29153514 - 26 Jul 2024
Cited by 6 | Viewed by 1852
Abstract
The main feature of neurodegenerative diseases, including Alzheimer’s disease, is the network of complex and not fully recognized neuronal pathways and targets involved in their onset and progression. The therapeutic treatment, at present mainly symptomatic, could benefit from a polypharmacological approach based on [...] Read more.
The main feature of neurodegenerative diseases, including Alzheimer’s disease, is the network of complex and not fully recognized neuronal pathways and targets involved in their onset and progression. The therapeutic treatment, at present mainly symptomatic, could benefit from a polypharmacological approach based on the development of a single molecular entity designed to simultaneously modulate different validated biological targets. This strategy is principally based on molecular hybridization, obtained by linking or merging different chemical moieties acting with synergistic and/or complementary mechanisms. The coumarin core, widely found in nature, endowed with a recognized broad spectrum of pharmacological activities, large synthetic accessibility and favourable pharmacokinetic properties, appears as a valuable, privileged scaffold to be properly modified in order to obtain compounds able to engage different selected targets. The scientific literature has long been interested in the multifaceted profiles of coumarin derivatives, and in this review, a survey of the most important results of the last four years, on both natural and synthetic coumarin-based compounds, regarding the development of anti-Alzheimer’s compounds is reported. Full article
(This article belongs to the Special Issue Coumarin and Its Derivatives III)
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