SYNTHESIS AND PHOTOBIOLOGICAL PROPERTIES OF 3-ACYLANGELICINS, 3-ALKOXYCARBONYLANGELICINS AND RELATED DERIVATIVES

Convenient synthesis of 3-acyl-2H-furo[2,3-h]-1-benzopyran-2-one ester s of 2-oxo-2H-furo[2,3-h]-1-benzopyran-3-carboxylic acid and 2H-furo[2 ,3-h]-1-benzopyran-3-carboxamides was accomplished via aromatization o f the adducts obtained by a reaction between thylaminomethylene-6,7-di hydrobenzofulan-4(5H)-one and the appropriate acylacetate or dialkyl m alonate. These compounds are angelicin derivatives which were prepared with the aim of obtaining intrinsically monofunctional drugs for phot ochemotherapy, with only one photoreactive site in their molecule. The new angelicins appear to be free df the known phototoxicity of furoco umarins on the skin and at a genetic level. The 3-carboxylic esters sh owed significant antiproliferative activity in Ehrlich ascites cells a nd T2 bacteriophage; the other derivatives were only slightly effectiv e. The features of these compounds are such that they represent a new model for non-toxic agents for photochemotherapy.