Master Degree / Yüksek Lisans Tezleri
Permanent URI for this collectionhttps://hdl.handle.net/11147/3008
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Master Thesis Synthesis of 1,5-Disubstituted 1,2,3-Triazole Modified Azacoumarins(01. Izmir Institute of Technology, 2022) Çağır, Ali; Çağır, Ali; 04.01. Department of Chemistry; 04. Faculty of Science; 01. Izmir Institute of TechnologyCancer is a deadly disease that threatens human health and all life, and it is still a serious problem despite all scientific studies for more than half a century. Pharmacophores are a part of the structure of a drug (or drug candidate) responsible from the biological activity. This thesis is related with the synthesis of novel compounds having two well-known pharmacophore structures, 1,2,3-triazole and 1-azacoumarin. Both structures can be found in the structure of many biologically active molecules. Triazole modified coumarin derivatives are scarce in the literature. In this study, we aimed to improve the synthetic route toward the synthesis of 1- azacoumarin derivative modified by 1,2,3-triazole group at position 4-. Synthesis starts with the conversion of methyl 4-chloroanthranilate to the corresponding 4-OH azacoumarin. Then it is transferred into the 4-OTf group by simply addition of Tf group to OH under basic condition. After Sonogashira reaction and removal of TMS group 4- alkynyl-1-azacoumarin was produced. At this point, conversion of alkyne into 1,5- disubstituted 1,2,3-triazole was examined in the presence of Cp2Ni-Xantphos and RuCl(COD)Cp* catalytic systems but all of trials were failed probably due to the presence of ester group close to the reaction site. In further studies, design of the molecule will be reperformed and ester group will be moved over phenyl rings in order to test its biological activity over cancer cell lines.Master Thesis Synthesis of Simple 2'-alkoxymethyl Substituted Klavuzon Derivatives(Izmir Institute of Technology, 2017) Çetinkaya, Hakkı; Çağır, Ali; Çağır, Ali; 04.01. Department of Chemistry; 04. Faculty of Science; 01. Izmir Institute of Technologyα,β-Unsaturated δ-lactones are the members of lactones, which are cyclic esters. They are quite valuable compounds because of their Michael acceptor property at unsaturated carbonyl functional group. It is believed that soft nucleophilic parts of the enzymes react with the β-carbon of lactone and form a covalent bond. If that is occurred at the active site of an enzyme, its activity is inhibited irreversibly. (R)-goniothalamin is a α,β-unsaturated lactone and it was shown that it has a selective cytotoxic activity over cancer cells. It is less cytotoxic in healthy cells. Later, Kasaplar and coworkers synthesized the klavuzon derivatives, which can be considered as the close relatives of goniothalamins. In this study novel derivatives of simple 2’-alkoxymethyl substituted klavuzon derivatives were synthesized. For this purpose, we started with 2-methyl-1-naphtoic acid, which can be transferred to ethyl 2-methyl-1-naphtoate by reacting with iodoethane under basic condition. Next, formed ester reacted with Br2 molecules generated in situ by NaBrO3 and NaHSO3. Then formed ethyl 2-(bromomethyl)-1-naphtoate reacted with various alcohols under basic conditions to form ethyl-2-alkoxymethyl-1-naphtoate. These esters are coverted to the target klavuzon products in five steps that are reduction with LiAlH4, oxidation with PCC, addition of allylmagnesium bromide, acrylate ester formation and ring closing metathesis reactions.