Synthesis of Novel 1,2-Diphenylpyrrole Derivatives Using Organophosphorus Reagents and Their Antitumour Activities

Abstract

The reactions are reported of 4-(furan-3-ylcarbonyl)-1,5-diphenylpyrrolidine-2,3-dione with six classes of organophosphorus reagents: carboalkoxymethylene triphenylphosphoranes, triphenyl (phenylimino)-λ 5 -phosphane, trialkylphosphonoacetates, trialkylphosphites, tris (dialkylamino)phosphines, and Lawesson's reagent. Several of the products showed antitumour activity.

Synthesis, Characterization and Antimicrobial Evaluation of New cis-Bicyclo [3.3.0] octane-3,7- dione Derivatives

“…Moreover, when dione 1 was reacted with Japanese reagent 4b in refluxing toluene for 1h, the corresponding 2-(phenylthio)tetrahydro-1'H-spiro[ [1,3,2] dithiaphosphetane-4,2'-pentalen]-5'(3'H)-one 2-sulfide (13) was obtained in a 40% yield (Scheme 5). The elemental microanalyses and spectroscopic data (IR, 1 H, 13 C, 31 P NMR, and MS data) agreed with structure of 13. Structure 13 was confirmed by the presence of one signal at 78.3 ppm (s) in its 31 P NMR spectrum.…”

“…Triphenylphosphorane oxide (TPPO) was also isolated from the reaction medium and identified (Scheme 2). The structure of compo und 8 was inferred from elemental analysis, IR, 1 H, 13 C, 31 P NMR, and MS data (cf. Experimental Section).…”

“…A second ylide molecule of 2e is then added to the ketene to afford compound 10 in a crystalline form (Scheme 3). The structure of compound 10 was deduced from elemental analysis, IR, 1 H, 13 C, 31 P NMR, and MS data (cf. Experimental Section).…”

“…Structure 13 was confirmed by the presence of one signal at 78.3 ppm (s) in its 31 P NMR spectrum. Moreover, 13…”

The Behaviour of Bis(Diphenylphosphino)Alkanes towards Different Active Centres

“…15 Bis(diphenylphosphino)alkanes have been reported as anticancer agents. [16][17][18][19][20] The useful applications of these starting materials, coupled with our interest in organophosphorus chemistry, [21][22][23][24][25] encouraged us to synthesise new organophosphorus compounds and to identify the preferred site of attack of these compounds. We sought to obtain the target compounds by reacting bis(diphenylphosphino) alkanes 1a-c with some different organic compounds; namely, benzophenone 2, 1,1′-(azodicarbonyl)dipiperidine (ADDP, 3), isatin 4a and 4b, and quinoxaline 1,4-di-N-oxide 5 (Scheme 1).…”