An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Abstract

Privileged structures have been widely used as an effective template for the research and discovery of high value chemicals. Coumarin is a simple scaffold widespread in Nature and it can be found in a considerable number of plants as well as in some fungi and bacteria. In the last years, these natural compounds have been gaining an increasing attention from the scientific community for their wide range of biological activities, mainly due to their ability to interact with diverse enzymes and receptors in living organisms. In addition, coumarin nucleus has proved to be easily synthetized and decorated, giving the possibility of designing new coumarin-based compounds and investigating their potential in the treatment of various diseases. The versatility of coumarin scaffold finds applications not only in medicinal chemistry but also in the agrochemical field as well as in the cosmetic and fragrances industry. This review is intended to be a critical overview on coumarins, comprehensive of natural sources, metabolites, biological evaluations and synthetic approaches.

Synergy, Additivity, and Antagonism between Cisplatin and Selected Coumarins in Human Melanoma Cells

“…It has been shown that they possess anticancer [ 25 ], antibacterial [ 26 ], antifungal [ 27 ], anti-inflammatory and antiviral [ 28 ], anticonvulsant [ 29 ], antihyperglycemic [ 30 ], triglyceride-lowering [ 31 ], antioxidant [ 32 ], bronchodilator [ 33 ], and vasodilator [ 34 ] effects. The molecular modeling of coumarins and various types of substitutions in their nuclei, represented by benzo-α-pyrone, may open new directions in the search and design of new, more potent compounds as effective adjuvants for the treatment of various diseases [ 35 ]. The interest in coumarins as potential anticancer agents in the treatment of tumors results from both in vitro and in vivo studies reporting that these compounds are effective in preventing the proliferation of bladder cancer [ 36 ], colon cancer [ 37 ], lung cancer [ 38 ], leukemia [ 39 ], and breast cancer [ 40 ] through different mechanisms of action, including cell cycle arrest, modulation of estrogen receptors, inhibition of DNA-associated enzymes such as topoisomerase [ 41 ], inhibition of angiogenesis, several types of heat shock proteins, and activity of enzymes involved in the pathophysiology of cancer, such as telomerase, monocarboxylate transporters, carbonic anhydrase, aromatase, and sulfatase [ 42 ], as well as modulation of different signaling pathways, such as the regulation of mitogen-activated protein kinase expression, signal transducers, and activators of transcription 3, phosphatidylinositol-3-kinase/AKT, and nuclear factor kB [ 43 ].…”

Trending Topics on Coumarin and Its Derivatives in 2020

“…Their conjugated double ring system makes them interesting molecules for different fields of research. Coumarins can be found in industry as cosmetics and perfume ingredients, as food additives, and especially in the pharmaceutical industry in the synthesis of a large number of synthetic pharmaceutical products [ 1 ]. This last application is the main focus of our overview.…”

Synthetic Routes to Coumarin(Benzopyrone)-Fused Five-Membered Aromatic Heterocycles Built on the α-Pyrone Moiety. Part 1: Five-Membered Aromatic Rings with One Heteroatom

“…Coumarins are a family of benzopyrones (1,2-benzopyrones or 2 H -[1]benzopyran-2-ones), which represent an important family of oxygen-containing heterocycles, widely distributed in nature [ 1 , 2 , 3 , 4 ]. Coumarins display a broad range of biological and pharmacological activities, [ 5 , 6 ] such as antiviral [ 7 , 8 , 9 , 10 ], anticancer [ 11 , 12 , 13 ], antimicrobial [ 14 , 15 ], and antioxidant [ 16 , 17 , 18 ] activities. On the other hand, coumarin represents an ingredient in perfumes [ 19 ], cosmetics [ 20 ], and as industrial additives [ 21 , 22 ].…”