Furocoumarins in medicinal chemistry. Synthesis, natural occurrence and biological activity.
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.
Santana
L
L
Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago, 15782, Santiago de Compostela, Spain. qofuri@usc.es
Uriarte
E
E
Roleira
F
F
Milhazes
N
N
Borges
F
F
D000818:Animals; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D011564:Furocoumarins / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000378:metabolism* / Q000494:pharmacology; D006801:Humans; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
D011564:Furocoumarins; D010936:Plant Extracts