Abstract

Synthesis and characterization of promising carboranylquinazolines for boron neutron capture therapy of tumors

Author(s): Afaf R.Genady

Novel classes of structurally different boronated quinazolines were designed bearing 22-37%boron byweight for potential application in BNCT of tumors. Firstly, the o-carborane cage was linked to quinazoline at C-2 position via thioether linker: 2-S-(1,2-dicarba-closo-dodecaboran(12)-1-yl)- 3-phenylquinazolin-4(3H)-one. Secondly, the o-carborane cage connected to quinazoline moiety at C-4 position through an ether linkage: 4-O-(ocarboran- 1-yl)-2-methylquinazoline. Finally, carboranemoietieswere also linked to the C-6 position of quinazoline: 6-[N-{3-(2-methyl-1,2-dicarbacloso- dodecaboran(12)-1-yl)methyl}benzylidinamino]quinazolin-4(3H)-one and 6-[N-{3,5-di(2-methyl-1,2-dicarba-closo-dodecaboran(12)-1 yl)methyl}benzylidinamino]quinazolin-4(3H)-one. Thewater solubilitywas achieved by the degradative conversion of the o-carboranylquinazolines to the corresponding potassium nido-carboranylquinazolines: 2-S-(1,2- dicarba-nido-undecacarborate-1-yl)-3-phenylquinazolin-4(3H)-one, 4-O- (1,2-dicarba-nido-undecacarborate-1-yl)-2-methylquinazoline, 6-[N-{3-(2- methyl-1,2-dicarba-nido-undecacarborate-1-yl)methyl}benzylidinamino] quinazolin-4(3H)-one and 6-[N-{3,5-di(2-methyl-1,2-dicarba-nidoundecacarborate- 1-yl)methyl}benzylidinamino]quinazolin-4(3H)-one. The products were confirmed byNMR, elemental analysis, IR, and mass spectrometry. The compounds described here can be considered as new candidates for BNCT.