Dissertation/ Thesis
Sinteza novih izoksazolnih i amidoksimskih bioizostera purina s antitripanosomskim djelovanjem ; Synthesis of new isoxazole and amidoxime purine bioisosteres with antitrypanosomal activity
| العنوان: | Sinteza novih izoksazolnih i amidoksimskih bioizostera purina s antitripanosomskim djelovanjem ; Synthesis of new isoxazole and amidoxime purine bioisosteres with antitrypanosomal activity |
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| المؤلفون: | Damjanović, Lorena |
| المساهمون: | Raić-Malić, Silvana |
| بيانات النشر: | Sveučilište u Zagrebu. Fakultet kemijskog inženjerstva i tehnologije. University of Zagreb. Faculty of Chemical Engineering and Technology. |
| سنة النشر: | 2024 |
| المجموعة: | Croatian Digital Theses Repository (National and University Library in Zagreb) |
| مصطلحات موضوعية: | PRIRODNE ZNANOSTI. Kemija, NATURAL SCIENCES. Chemistry, benzotiazol, benzimidazol, izoksazol, 1 3-dipolarna cikloadicija, purin, purinski bioizosteri, benzothiazole, benzimidazole, isoxazole, 1 3-dipolar cycloaddition, purine, purine bioisoteres |
| الوصف: | U ovom radu opisana je sinteza novog amidoksim-supstituiranog derivata benzotiazola 5 te novih hibrida benzimidazola i izoksazola 19a–e. Derivat 5 dobiven je višestupanjskom sintezom iz 4-aminobenzonitrila. Utvrđeno je da derivat 5 pokazuje antitripanosomsku aktivnost s IC50 vrijednosti od 0.92 μM, uz indeks selektivnosti 18. Zbog izražene biološke aktivnosti i visoke selektivnosti, derivat je korišten kao ligand za sintezu metalnih kompleksa renija(I) i mangana(I). N-propargilirani derivat benzimidazola 12 dobiven je reakcijom alkiliranja dok su odgovarajući oksimi 18a–e, potrebni za sintezu izoksazolnih derivata priređeni reakcijom kloriranja odgovarajućih aldoksima. Ciljani derivati 19a–e priređeni su bazno-kataliziranom 1,3-dipolarnom cikloadicijom iz N-propargiliranog derivata 12 i kloriranih oksima 18a–e. Strukture novosintetiziranih spojeva potvrđene su spektroskopijom 1H i 13C NMR. Naknadno će se provesti antitripanosomska ispitivanja ostalih novosintetiziranih spojeva. ; In this work, the synthesis of novel amidoxime derivatives of benzothiazole 5 and novel benzimidazole derivatives linked via an isoxazole spacer (19a–e) is described. Derivative 5 was obtained from 4-aminobenzothiazole by a multi-step synthesis. Derivative 5 was evaluated for its antitrypanosomal activity and gave an IC50 value of 0.92 μM against T. brucei, with a selectivity index of 18. Due to its significant biological activity and high selectivity, the derivative was used as a ligand for the synthesis of rhenium(I) and manganese(I) metal complexes. N-Propargylated benzimidazole derivative 12 was prepared by alkylation reaction. The corresponding oximes 18a–e for the synthesis of isoxazole derivatives were synthesized by the chlorination reaction of corresponding aldoximes. The targer isoxazole derivatives 19a–e were prepared by base-catalyzed 1,3-dipolar cycloaddition of N-propargylated benzimidazole derivative 12 and chlorinated oximes 18a–e. The structures of all compounds were determined by 1H NMR and 13C NMR spectroscopy. ... |
| نوع الوثيقة: | master thesis |
| وصف الملف: | application/pdf |
| اللغة: | Croatian |
| Relation: | info:eu-repo/grantAgreement/Hrvatska zaklada za znanost/Research Projects/IP-2022-10-9420/HR/Novi N‐heterocikli i njihovi kompleksi s antitumorskim i antitripanosomskim djelovanjem/NHet&MetCom Project; https://zir.nsk.hr/islandora/object/fkit:2930; https://urn.nsk.hr/urn:nbn:hr:149:203445; https://repozitorij.unizg.hr/islandora/object/fkit:2930; https://repozitorij.unizg.hr/islandora/object/fkit:2930/datastream/PDF |
| الاتاحة: | https://zir.nsk.hr/islandora/object/fkit:2930 https://urn.nsk.hr/urn:nbn:hr:149:203445 https://repozitorij.unizg.hr/islandora/object/fkit:2930 https://repozitorij.unizg.hr/islandora/object/fkit:2930/datastream/PDF |
| Rights: | http://rightsstatements.org/vocab/InC/1.0/ ; info:eu-repo/semantics/embargoedAccess |
| رقم الانضمام: | edsbas.4DA5962C |
| قاعدة البيانات: | BASE |
| الوصف غير متاح. |