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Synthesis and Bioactivity of Coumarin and Coumarin Derivatives
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Synthesis and Bioactivity of Coumarin and Coumarin Derivatives

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 July 2020) | Viewed by 12566

Special Issue Editor

Prof. Dr. Konstantinos E. Litinas

E-Mail Website
Guest Editor
Aristotle University of Thessaloniki, Department of Chemistry, Thessaloniki, Greece
Interests: organic synthesis; natural products synthesis; coumarin derivatives; purine derivatives; modified N-homonucleosides; synthesis of compounds with possible biological activity; application of organometallic reagents in organic synthesis (olefin metathesis, cross-coupling reactions); synthesis under microwaves

Special Issue Information

Dear Colleagues,

Coumarin (2H-1-benzopyran-2-one) is wide spread as an essential core moiety in a variety of natural products occurring in plants, bacteria, and fungi. Coumarin is synthesized in nature through the shikimate biosynthetic pathway, and it is also metabolized to hydroxycoumarins. Coumarins present interesting biological properties, such as anticoagulant, antibiotic, anti-inflammatory, antioxidant, anti-HIV, anticancer, thermal photosensitizing, vasodilator, and estrogenic activity.

Especially, hydroxycoumarin derivatives are used as anticoagulant, antibiotic, or choleretic drugs. 7-Aminocoumarins are useful as biological sensors showing fluorescence activity. Fused furanocoumarin derivatives are used for treating psoriasis, and they also exhibit anti-inflammatory, antibacterial, antifungal, and cytochrome P-450 inhibitor properties. Fused pyranocoumarins present anti-HIV, anticancer, anti-inflammatory, antifungal activities, and they play an important role in the regulation of root growth in different plants. Fused pyrrolocoumarins possess cytotoxic, anti-HIV, anti-inflammatory, photobiological, and antiproliferative properties. Fused pyridocoumarins present anticholinergic, antidiabetic, antiallergic, antipsychotic, and antimicrobial activities.

Prof. Dr. Konstantinos E. Litinas
Guest Editor

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Keywords

  • Coumarin synthesis
  • Coumarin bioactivity
  • Coumarin derivatives
  • Hydroxycoumarins
  • Aminocoumarins
  • Fused coumarins
  • Furanocoumarins
  • Pyranocoumarins
  • Pyrrolocoumarins
  • Pyridocoumarins

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Published Papers (2 papers)

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19 pages, 32648 KiB  
Article
Pretreatment with Warfarin Attenuates the Development of Ischemia/Reperfusion-Induced Acute Pancreatitis in Rats
by Dawid Maduzia, Piotr Ceranowicz, Jakub Cieszkowski, Krystyna Gałązka, Beata Kuśnierz-Cabala and Zygmunt Warzecha
Molecules 2020, 25(11), 2493; https://doi.org/10.3390/molecules25112493 - 27 May 2020
Cited by 19 | Viewed by 3155
Abstract
In acute pancreatitis (AP), pancreatic damage leads to local vascular injury, manifesting as endothelial damage and activation, increased vascular permeability, leukocyte rolling, sticking and transmigration to pancreatic tissue as well as activation of coagulation. Previous studies have shown that pretreatment with heparin or [...] Read more.
In acute pancreatitis (AP), pancreatic damage leads to local vascular injury, manifesting as endothelial damage and activation, increased vascular permeability, leukocyte rolling, sticking and transmigration to pancreatic tissue as well as activation of coagulation. Previous studies have shown that pretreatment with heparin or acenocoumarol inhibits the development of AP. The aim of the present study was to check the impact of pretreatment with warfarin, an oral vitamin K antagonist, on the development of ischemia/reperfusion-induced AP in rats. AP was induced by pancreatic ischemia followed by reperfusion of the gland. Warfarin (90, 180 or 270 µg/kg/dose) or vehicle were administered intragastrically once a day for 7 days before induction of AP. The effect of warfarin on the severity of AP was assessed 6 h after pancreatic reperfusion. The assessment included histological, functional, and biochemical analyses. Pretreatment with warfarin given at a dose of 90 or 180 µg/kg/dose increased the international normalized ratio and reduced morphological signs of pancreatic damage such as pancreatic edema, vacuolization of acinar cells, necrosis and the number of hemorrhages. These effects were accompanied by an improvement of pancreatic blood flow and a decrease in serum level amylase, lipase, pro-inflammatory interleukin-1β and plasma level of D-dimer. In contrast, pretreatment with warfarin given at a dose of 270 µg/kg/dose led to an increase in severity of pancreatic damage and biochemical indicators of AP. In addition, this dose of warfarin resulted in deaths in some animals. Pretreatment with low doses of warfarin inhibits the development of AP induced by pancreatic ischemia followed by reperfusion. Full article
(This article belongs to the Special Issue Synthesis and Bioactivity of Coumarin and Coumarin Derivatives)
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Review

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24 pages, 8656 KiB  
Review
Antagonists of Vitamin K—Popular Coumarin Drugs and New Synthetic and Natural Coumarin Derivatives
by Kinga Kasperkiewicz, Michał B. Ponczek, Jacek Owczarek, Piotr Guga and Elżbieta Budzisz
Molecules 2020, 25(6), 1465; https://doi.org/10.3390/molecules25061465 - 24 Mar 2020
Cited by 67 | Viewed by 8660
Abstract
Many natural coumarins and their chemically synthesized analogs and derivatives exert diverse properties, such as anticancer, antioxidant, anti-inflammatory, or anticoagulant, with the latter being of the utmost importance. The widely used warfarin, acenocoumarol, and phenprocoumon exert anticoagulant properties by inhibiting the vitamin K [...] Read more.
Many natural coumarins and their chemically synthesized analogs and derivatives exert diverse properties, such as anticancer, antioxidant, anti-inflammatory, or anticoagulant, with the latter being of the utmost importance. The widely used warfarin, acenocoumarol, and phenprocoumon exert anticoagulant properties by inhibiting the vitamin K epoxide reductase complex. In this interdisciplinary review, we present biochemical principles of the coagulation processes and possible methods for their tuning based on the use of coumarins. We also summarize chemical methods of synthesis of coumarins and discuss structures and properties of those that have been used for a long time, as well as newly synthesized compounds. Brief information on the clinical use of coumarins and other anticoagulant drugs is given, including the severe effects of overdosing and methods for reversing their action. Full article
(This article belongs to the Special Issue Synthesis and Bioactivity of Coumarin and Coumarin Derivatives)
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