Coumarins Synthesis and Transformation via C–H Bond Activation—A Review

Abstract

For several decades, coumarins have attracted considerable attention due to the fact of their application in diverse fields such as medical science and biomedical research as well as several industrial branches. Recently, many compounds containing the coumarin moiety have been intensively studied, mainly due to the fact of their biological activities such as antitumor, antioxidative, anti-HIV, vasorelaxant, antimicrobial, and anticancer. They are also widely used as fluorescent dyes and probes because of their great structural flexibility and large fluorescent quantum yields. For this reason, numerous attempts have been made to develop new and more practical methods for the synthesis of these compounds. This review aims at providing a comprehensive overview of coumarin synthesis methods by direct C–H bond activation in order to demonstrate the current state-of-the-art methods as well as the current limitations.

4-(Phenylselanyl)-2H-chromen-2-one-Loaded Nanocapsule Suspension—A Promising Breakthrough in Pain Management: Comprehensive Molecular Docking, Formulation Design, and Toxicological and Pharmacological Assessments in Mice

“…where Dv (90), Dv (10), and Dv (50) are the diameters at 90%, 10%, and 50% of the cumulative distribution of the diameter curve, respectively. The zeta potential was determined by electrophoretic mobility (Zetasizer ® Nano-ZS ZEN 3600 model, Malvern Instruments, UK).…”

“…The release profile of 4-PSCO from polymeric nanocapsules was performed in triplicate by the dialysis bag diffusion method [43]. An aliquot of 1 mL of 4-PSCO-loaded polymeric nanocapsules was placed inside the dialysis cellulose membrane (molecular weight 10,000 Da, Sigma-Aldrich, St. Louis, MI, USA) and immersed in 200 mL of release medium composed of 70% of the 1 M potassium phosphate buffer at pH 7.4 and 30% of ethanol kept under moderate magnetic stirring at 37 • C. At predetermined times (1,2,3,4,5,6,8,10,12,24, and 48 h), 1 mL of the external medium was collected, and the same volume of fresh medium was replaced. The quantity of 4-PSCO released was assessed by the HPLC method previously described in Section 2.4.…”

“…However, it is known that organic selenium compounds have numerous pharmacological targets, and, for this reason, are capable of causing a complex pattern of action, and this characteristic can lead to molecular toxicity [ 9 ]. In this way, coumarins, regarded as privileged structures in medicinal chemistry, offer straightforward synthesis and versatile functionalization within the coumarin ring, yielding derivatives with compelling applications and biological activities [ 10 ]. These compounds exhibit notable antioxidant, anti-inflammatory, antitumoral, antimicrobial, and antiviral actions, supported by a body of literature [ 8 , 11 , 12 , 13 ].…”

Deep Red to NIR Emitting Xanthene Hybrids: Xanthene‐Hemicyanine Hybrids and Xanthene‐Coumarin Hybrids

“…Various deep red to NIR chromophores/fluorophores such as squaraine, [19][20][21] azo, [22][23][24] styryl, [25][26][27] perylene, [28][29][30] BODIPY, [31][32][33] aza-BODIPY, [32,34,35] cyanine, [36][37][38] coumarin, [39,40] and xanthene [41][42][43] are reported having either absorption or emission or both lying in the deep-red to NIR. A few such fluorophores are presented in Figure 1.…”

Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions

“…The presence of the coumarin structure in natural products and biologically active molecules has promoted considerable interest toward their synthesis [ 1 , 2 , 3 ]. The coumarin framework is widely used as a building block for obtaining derivatives that exhibit a wide variety of biological properties [ 4 ], especially anti-HIV, antitumor, anticoagulant, and antibiotic activities [ 5 ].…”