Derivatives of tyrosine with an acetylene type of substituents

Endiinski antitumorski antibiotici predstavljaju novu skupinu spojeva složene strukture, izražene biološke aktivnosti i jedinstvenog mehanizma djelovanja. U svrhu dobivanja jednostavnijih analoga endiina, u okviru ovog diplomskog rada priređeni su derivati tirozina modificirani na karboksilnom i amino-kraju, te u bočnom lancu, s propargilnim (prop-2-inil) supstituentima. Dobiveni i karakterizirani su sljedeći spojevi: N,O-di-tert-butiloksikarbonil-L-tirozin N-propargilamid (3), L-tirozin N-propargilamid (4), N-(2-nitrobenzensulfonil)-L-tirozin N-propargilamid (5), N-(2-nitrobenzensulfonil)-N,O-dipropargil-L-tirozin N-propargilamid (7), N-propargil-L-tirozin N-propargilamid (8), N,O-dipropargil-L-tirozin N-propargilamid (9) i N-tert-butiloksikarbonil-O-propargil-L-tirozin N-propargilamid (10).Enediyne anticancer antibiotics represent a new class of compounds with complex architecture, high biological activity and the unique mechanism of action. As a part of the ongoing studies on the synthesis of enediyne analogs, within the framework of this Graduated paper tyrosine derivatives carrying propargyl substituents at the N- and C-terminus, as well as the side chain, have been prepared. The following products are synthesized and characterized: N,O-di-tert-butyloxycarbonyl-L-tyrosine N-propargylamide (3), L-tyrosine N-propargylamide (4), N-(2-nitrobenzenesulfonyl)-L-tyrosine N-propargylamide (5), N-(2-nitrobenzenesulfonyl)-N,O-dipropargyl-L-tyrosine N-propargylamide (7), N-propargyl-L-tyrosine N-propargylamide (8), N,O-dipropargyl-L-tyrosine N-propargylamide (9) and N-tert-butyloxycarbonyl-O-propargyl-L-tyrosine N-propargylamide (10)