Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Abstract

Coumarins, also known as benzopyrones, are present in remarkable amounts in plants, although their presence has also been detected in microorganisms and animal sources. The structural diversity found in this family of compounds led to the division into different categories, from simple coumarins to many other kinds of policyclic coumarins, such as furocoumarins and pyranocoumarins. Simple coumarins and analogues are a large class of compounds that have attracted their interest for a long time due to their biological activities: they have shown to be useful as antitumoural, anti-HIV agents and as CNS-active compounds. Furthermore, they have been reported to have multiple biological activities (anticoagulant, anti-inflammatory), although all these properties have not been evaluated systematically. In addition, their enzyme inhibition properties, antimicrobial and antioxidant activities are other foremost topics of this field of research. The present work is to survey the information published or abstracted from 1990 till 2003, which is mainly related to the occurrence, synthesis and biological importance of simple coumarins and some analogues, such as biscoumarins and triscoumarins. Data are also highlighted, concerning the development of new synthetic strategies that could help in drug design and in the work on SAR or QSAR.

Copper(II) complexes of coumarin-derived Schiff bases and their anti-Candida activity

“…Many of the coumarins present in plants, and also their synthetic analogues, have been reported to be good antifungal and antibacterial agents [14][15][16][17][18][19][20][21]. Preliminary structure-activity relationship studies have shown that the presence of hydroxyl or carboxylic groups on the coumarin nucleus are necessary for antimicrobial activity [22]. We have previously published a number of studies on both carboxylate-and hydroxy-substituted coumarin ligands, and while the ligands themselves were not active against fungal species a number of their Ag(I) and Cu(II) complexes showed good antimicrobial activity [23][24][25].…”

In vitro cytotoxic, antioxidant and antiviral effects of Pterocaulon alopecuroides and Bidens segetum extracts

“…Coumarins are a group of natural compounds which are extremely variable in structure (Beillerot et al, 2008), leading to compounds displaying multiple biological properties as in vitro antiproliferative and in vivo antitumor activities (Kostova, 2005); antioxidant activity (Beillerot et al, 2008;Farombi and Nwaokeafor, 2005;Fylaktakidou et al, 2004;Girennavar et al, 2007;Kontogiorgis et al, 2004;Torres et al, 2006;Wua et al, 2007;von Kruedener et al, 1996); inhibitory activity against cytochrome P450 enzyme (Girennavar et al, 2007); neuroprotective, anticancer and antimutagenic activities (Borges et al, 2005;Stanczyk et al, 2005); anti-inflammatory activity (Borges et al, 2005;Khan and Sharma, 1993;Kontogiorgis et al, 2004;Stanczyk et al, 2005); vasorelaxant (Hoult and Paya, 1996) and anticoagulant activities (Khan and Sharma, 1993). Some studies reveal that the multiple pharmacological activities of coumarins may be related to their antioxidant properties (Borges et al, 2005;Stanczyk et al, 2005), as oxidative damage to biomolecules causes accelerated aging and many chronic diseases, including neurodegenerative diseases, cancer, cardiovascular …”

“…Some studies reveal that the multiple pharmacological activities of coumarins may be related to their antioxidant properties (Borges et al, 2005;Stanczyk et al, 2005), as oxidative damage to biomolecules causes accelerated aging and many chronic diseases, including neurodegenerative diseases, cancer, cardiovascular …”

3-Arylcoumarins: Synthesis and potent anti-inflammatory activity

“…They have been reported with anticancer, antioxidant, anti-inflammatory, antimicrobial, antiviral and enzyme-inhibitory activities. 5 Hyuganin A-D, anomalin and isopteryxin from the roots of Angelica furcijuga KITAGAWA, 6 fukanefuromarin D from the roots of Ferula fukanensis 7 and a series of coumarins from the flowers of Mammea siamensis (Calophyllaceae) 8 demonstrated potent inhibitory activity on lipopolysaccharide (LPS)-induced NO production in mouse macrophages (Fig. 1).…”

“…5 The most wildly used method was Perkin reaction staring from salicylaldehyde in the presence of base and acid anhydride. 11 In this work, we present the synthesis of manifold 3-aryl substituted coumarins and their inhibitory activity on LPS-induced NO production in RAW 264.7 cells.…”