SILICON-MEDIATED INACTIVATION OF DIAMINE OXIDASE

The design, synthesis, and biologic evaluation of potential silicon-co ntaining inhibitors of diamine oxidases (siladiaminopropane 1, silaput rescine 2, and sila analogs of cadaverine 3, 4, and 5) are described. All compounds have been prepared independently. The common feature in the reported syntheses is the way chosen to introduce the amine group relative to silicon: the Gabriel-type approach to obtaining aminomethy l- and aminopropylsilanes and the Mitsunobu-type approach to obtaining aminoethylsilanes. Among the synthesized silane diamines, compounds 1 and 3 have been found to be time-dependent inhibitors of diamine oxid ases prepared from hog kidney and rat small intestine. These results e xtend and generalize the concept of silicon-based inactivation of amin e oxidases. (C) 1996 Academic Press, Inc.