Sinteza novih aril-supstituiranih derivata kumarina i kinolina s potencijalnim citostatskim djelovanjem

undergraduate thesis

• Title (english): Synthesis of novel aryl-substituted coumarin and quinoline derivatives with potential cytostatic activity
• Author: Marina Ter
• Mentor: Silvana Raić-Malić (mentor)
• Committee member: Silvana Raić-Malić (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Danijela Ašperger (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2023-09-13, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Cilj ovog rada je sinteza novih aril-supstituiranih derivata kumarina i kinolina (5c−e, 6a−e, 7e, 8, 9) te njihovih Re(I)- (5d-Re, 8-Re, 10-Re) i Ru(II)-kompleksa (5d-Ru-fenil, 10-Ru-fenil, 5d-Ru-cim, 10-Ru-cim). Izoksazolni derivati kumarina i kinolina (5c−e, 6a−e, 7e) dobiveni su regioselektivnom 1,3-dipolarnom cikloadicijom propargiliranog kumarinskog (1) ili kinolinskog (2) derivata i odgovarajućeg kloriranog aldoksima (4a−e) uz trietilamin. Cijano-supstituirani izoksazolni derivati kinolina i kumarina (5e, 6e) prevedni su u fenilamidoksimske analoge (8, 9). Spojevi 5d i 10 korišteni su kao ligandi za metalne komplekse s renij(I) pentakarbonil-kloridom (5d-Re, 10-Re), diklor(benzen)rutenij(II) dimerom (5d-Ru-fenil, 10-Ru-fenil) i diklor(p-cimen)rutenij(II) dimerom (5d-Ru-cim, 10-Ru-cim). Strukture spojeva potvrđene su spektroskopijom 1H i 13C NMR, strukture cijano (6e) i fenilamidoksimskog (9) derivata kinolina potvrđene su spektroskopijom IR, a određivanje rendgenske strukture na monokristalu kompleksa te biološka ispitivanja novosintetiziranih spojeva (5−10, 5d-Re, 5d-Ru-fenil, 5d-Ru-cim, 10-Re, 10-Ru-fenil, 10-Ru-cim) su u tijeku.

Abstract (english)

The aim of this work was the synthesis of new aryl-substituted coumarin and quinoline derivatives (5c−e, 6a−e, 7e, 8, 9) and their Re(I)- (5d-Re, 8-Re, 10-Re) and Ru(II)-complexes (5d-Ru-phenyl, 10-Ru-phenyl, 5d-Ru-cym, 10-Ru-cym). Isoxazole derivatives (5c−e, 6a−e, 7e) were obtained by regioselective 1,3-dipolar cycloaddition of propargylated coumarin (1) or quinoline (2) derivative and corresponding chlorinated aldoximes (4a−e) with triethylamine. Cyano-substituted isoxazole derivatives (5e, 6e) were converted to their phenylamidoxime analogues (8, 9). Compounds 5d and 10 were used as ligands for metal complexes with rhenium(I) pentacarbonyl chloride (5d-Re, 10-Re), dichloro(benzene)ruthenium(II) dimer (5d-Ru-phenyl, 10-Ru-phenyl) and
dichloro(p-cymene)ruthenium(II) dimer (5d-Ru-cym, 10-Ru-cym). The structures of all compounds have been confirmed by 1H and 13C NMR spectroscopy, the structures of cyano (6e) and phenylamidoxime (9) quinoline derivatives are characterized by IR spectroscopy, while structure determination by X-ray diffraction on single crystals of complexes and biological evaluations of newly synthesized compounds (5-10, 5d-Re, 5d-Ru-phenyl, 5d-Ru-cym, 10-Re, 10-Ru-phenyl, 10-Ru-cym) are in progress.

• Keywords: citostatska aktivnost; kinolin; kumarin; izoksazol; 1 3-dipolarna cikloadicija; metalni kompleksi
• Keywords (english): cytostatic activity; quinoline; coumarin; isoxazole; 1 3-dipolar cycloaddition; metal complexes
• Language: croatian
• URN:NBN: urn:nbn:hr:149:171307
• Study programme: Title: Applied Chemistry - Undergraduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Applied organic chemistry; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Embargoed access; Embargo expiration date: 2026-09-01
• Created on: 2023-09-14 12:10:17