Furocoumarins in Medicinal Chemistry. Synthesis, Natural Occurrence and Biological Activity

Abstract

The scope of this review encompasses the importance of furocoumarins and the most important developments in this field that have been made in recent years, with particular emphasis placed on the aspects related to medicinal chemistry. A concise and exhaustive overview is given regarding the methods used for the synthesis of these compounds, new furocoumarins isolated from natural sources, and the most significant biological properties associated with these molecules. The section describing the synthetic methods is organized on the basis of the key step used for the formation of the two different oxygenated rings. In this respect there are three possibilities: (i) formation of the furan ring onto the coumarin, (ii) formation of the pyrone ring onto the benzofuran and (iii) the simultaneous formation of both oxygenated rings onto a benzene unit. The most recent preparative approaches are discussed along with modifications or improvements to methods that, though not particularly new, are still commonly used. The recently discovered natural furocoumarins are focused and presented in tables that provide information about its structure and source. The discussion of the biological importance of furocoumarins mainly focuses on their more relevant applications in photochemotherapy, but also provides examples of their versatility in a range of applications in the fields of biology and pharmacology.

Synthesis and Anti-inflammatory Activity of Novel Furochromenes

“…27 Furocoumarins are a class of natural and synthetic compounds used as photoreactive, antiviral, antiinflammatory agents as well as kinase inhibitors. 28 Furo [4,3-c]coumarins are generally prepared by condensation of aryl substituted 4-hydroxycoumarins as dinucleophiles and vicinal dielectrophiles. 26,29 In a quest for new anti-inflammatory / antiallergic therapeutics we screened our compound collection in mast cell degranulation assays and leukotriene B 4 assay.…”

Herbal Remedies and New Approaches in Vitiligo Treatment

“…Bunun yanında, sentetik olarak da üretilen furokumarinler bulunmaktadır. 36,37 Furokumarinler, lineer (Psöralen türevleri) ve angular furokumarinler (Anjelisin türevleri) olarak iki grup altında incelenmektedirler. 38 Furokumarinler, psöriyazis ve vitiligo gibi farklı cilt rahatsızlıklarına karşı fotokimyasal tedavilerde, geniş şekilde kullanılmaktadır.…”

Discrimination of the seeds of Notopterygium incisum and Notopterygium franchetii by validated HPLC-DAD–ESI-MS method and principal component analysis

“…namely kynurenic acid (1), alaschanioside C (2), umbelliferone (3), bergaptol-O-␤-d-glucopyranoside (4), nodakenin (5), oxypeucedanin (6), bergapten (7), diosmetin (8), oxypeucedanin hydrate (9), O-prenyl-umbelliferone (10), phellopterin (11) and isoimperatorin (12) were isolated in our laboratory from the seeds of N. incisum and N. franchetii and their structures ( Fig. 1) were elucidated by comparison of UV, MS, 1 H NMR and 13 C NMR spectral data with the literature values [4,5,[23][24][25][26][27][28][29].…”

“…The chemical constituents from the rhizomes and roots of the two plants were coumarins, phenoloids and essential oils [3][4][5][6][7][8][9]. Pharmacological studies have shown that coumarins such as isoimperatorin, notopterol and bergapten possess anti-inflammatory, analgesic and anti-cancer activities [10][11][12][13][14].…”