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The design, synthesis, and biologic evaluation of potential silicon-containing inhibitors of diamine oxidases (siladiaminopropane 1 , silaputrescine 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 aminomethyl- 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 oxidases prepared from hog kidney and rat small intestine. These results extend and generalize the concept of silicon-based inactivation of amine oxidases. |
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