Synthesis of some medicinal and biological active (E)-2-arylidine-4-oxo-4-(4-(N-arylsulfamoyl)phenylamino)butanoic acids and (E)-4-(3-arylidene)-2,5-dioxopyrrolidin-1-yl)-N-arylbenzenesulfonamides

Microwave irradiation of anhydride (E)-3-(3,4-dimethoxybenzylidene)dihydrofuran-2,5-dione 1 gives with N-aryl-4-aminobenzenesulfonamides (a and d) separable mixtures of (E)-2-(3,4-dimethoxybenzylidene)-4-oxo-4-(4-(N-arylsulfamoyl)phenylamino)butanoic acids 3 and 6, and (E)-4-(3-(3,4-dimethoxybenzylidene)-2,5-dioxopyrrolidin-1-yl)-N-arylbenzenesulfonamides 10 and 13, respectively. Also anhydride (E)-3-(benzo[d][1,3]dioxol-5-ylmethylene)dihydrofuran-2,5-dione 2 gives with amines (a, b, d, and g), separable mixtures of (E)-2-(benzo[d][1,3]dioxol-5-ylmethylene)-4-oxo-4-(4-(N-arylsulfamoyl) phenylamino) butanoic acids 16, 17, 19 and 22, and (E)-4-(3-(benzo[d][1,3]dioxol-5-ylmethylene)-2,5-dioxopyrrolidin-1-yl)-N-aryl-benzenesulfonamides 23, 24, 26, and 28, respectively. On the other hand, reaction of 1 with amines (b, c, e, and g) gives benzenesulfonamides 11, 12, 14, and 15, whereas compound 2 gives with amines (c and e) the corresponding benzenesulfonamides 25 and 27, as only products. Compounds 1 and 2 give, either in presence or absence of solvent DMF, with amine (f) the corresponding butanoic acids 8 and 21, respectively. Microwave irradiation of (g) with 1 gives benzenesulfonamide 15 as an only product, whereas with 2, it gives a separable mixture of 22 and 28, whereas in DMF, it gives compound 28 as an only product. Reaction of 1 and 2 with (a-g) using the conventional thermal heating technique, gives the corresponding butanoic acid derivatives 3- 7, 9 and 16-20, 22, respectively. Trials to react 1 and 2 with (f) were unsuccessful. The structural formulas of the products obtained 3- 28 were assigned by their spectral analysis. Cytotoxic and antimicrobial activities of some prepared compounds have been studied and reported. [Boshra M. Awad, Shadia M. Abdallah, Halima A. Hefny, Mervat H. Abdou, Fatehia I. Abd-Elmonem and Noura A. Abd-Elmomem. Synthesis of some medicinal and biological active (E)-2-arylidine-4-oxo-4-(4-(N-arylsulfamoyl)phenylamino)butanoic acids and (E)-4-(3-arylidene)-2,5-dioxopyrrolidin-1-yl)-N-arylbenzenesulfonamides. Life Sci J 2012;9(4):567-577] (ISSN:1097-8135). http://www.lifesciencesite.com. 86