Organic molecules that may be effective in living systems

Amino acids are the simplest optically active compounds found in nature that their polymer, peptide and protein forms demonstrate functions such as electron transfer, information transfer, photoactivity and selective catalytic functions which are not shown by a wide variety of synthetic compounds. Natural and unnatural amino acids and their derivatives are widely used in asymmetric catalysis as chiral reagents, intermediates and ligands. On the other hand, malemide derivatives are an important substrate in biological and chemical applications. They are used in biological applications, chemical analyzes of protein constructs, cancer therapies as immune pairs, synthetic applications as solid-support enzymes, and also as new pesticides. The maleimide part could act as a platform in the synthesis thanks to the Michael accepter feature. Due to its dienophilic nature, it shows reactivity as much as dipolarophilia in 1,3-cyclocarbamates. There are several reports in the literature about the synthesis of N-substituted chiral maleimides with norbornenyl part in their skeleton. Biagini and colleagues synthesized amino acid methyl esters containing the norbornene structure [1]. In this thesis, we research on the synthesis of new chiral amino acid methyl esters containing aryl modified bicyclic imide systems by reducing Heck reaction. Due to its broad synthetic potential, Heck reactions, a stereoselective carbon-carbon bonding method, have been the subject of many synthetic and mechanistic studies over the past three decades. Peptides are polymeric structures formed by covalent bonding of one or more α-amino acids to each other. Protein molecules, building blocks of living cells, are obtained by forming long chain peptid bond. The covalent bond formed by the electron exchange between an amino acid and the other is known as an "amide bond" or peptide bond. In recent years there have been many new peptide molecule synthesis in the literature that may show biological activity. This study was designed after extensive literature research carried out mainly consists of nine steps. The first step is the synthesis of the optically active norbornenyl amino acid to be used as starting material. The second step is the synthesis of this amino acid's acyl chloride derivative. The third step is the synthesis of the alkenic peptide derivative, starting from the amino acid's acyl chloride derivative. Then, the alkenic peptid derivative is used as a starting material, and hydroarylation reactions are done with 1-iodobenzene, 4-morpholinoiodobenzene and 4-chloroiodobenzene reagents. In order to explain our one-side hydroarylation reactions, N-N hydrazide cleavage is done with 3,4-difluoroiodobenzene reagent. After that, domino-Heck reactions are carried out with phenyllacetylene, 1-iodobenzene reagents and phenyllacetylene, 4-chloroiodobenzene reagents, and new peptid derivatives are synthesized. In the final stage, our new peptid derivatives are extensively characterized by the use of spectroscopic studies such as FTIR, 1H NMR, 13C NMR, GC-MS and LC-MSMS/QTOF analyses. We think that these new compounds (compound 5, compound 8, compound 9, compound 10, compound 12) can show various biological activities and can be studied in living systems due to carrying the structures such as aryl, leucine chain, amide and imide which are important for pharmacological studies.